Butterfield (NYSE: NTB) plans $1.8B CIBC Caribbean acquisition, boosting assets to $29B

Rhea-AI Filing Summary

The Bank of N.T. Butterfield & Son Limited is making a transformational acquisition of CIBC Caribbean Bank Limited. Butterfield agreed to buy CIBC’s 91.7% stake for an aggregate purchase price of $1.794 billion, made up of $1.091 billion in cash and $703 million in Butterfield shares, valued using a 10-day VWAP of $55.66. The deal implies $1.14 per CIBC Caribbean share and includes issuing 11,577,367 new Butterfield ordinary shares at an exchange ratio of 0.008008 share plus $0.6918 in cash per CIBC Caribbean share.

Butterfield will also launch a mandatory takeover bid for the remaining 8.3% minority stake on equivalent economic terms, with minorities able to elect up to 100% stock. The bank has obtained commitments for $700 million of Tier 2 subordinated debt to help fund the cash portion and expects the combined institution to have about $29 billion in assets and $25 billion in deposits. Management projects 12% GAAP EPS accretion and 15% cash EPS accretion in the first full year with fully phased-in synergies, 10% tangible book value per share accretion at closing, and an internal rate of return above 20%, while maintaining a pro forma CET1 ratio above 12% and total capital above 19%. Pre-tax cost savings are expected to reach an annual run rate of roughly $49 million by 2030.

Positive

• Transformational scale and diversification: The deal creates a roughly $29 billion-asset institution with about $25 billion in deposits, broadening Butterfield’s presence across Bermuda, Cayman and multiple Caribbean markets and adding a granular, largely retail-funded deposit base.
• Accretive financial profile: Management projects 12% GAAP EPS accretion and 15% cash EPS accretion in the first full year with fully phased-in synergies, a 10% uplift to tangible book value per share at closing, and an internal rate of return above 20%.
• Strong pro forma capital metrics: Even after funding the $1.091 billion cash portion and issuing debt, the combined bank is expected to maintain a pro forma CET1 ratio above 12% and total capital above 19%, leaving a sizeable capital buffer.
• Meaningful cost synergies: Annual pre-tax cost savings are expected to reach about $49 million by 2030, supported by overlapping operations and similar IT platforms that can be rationalized over time.

Negative

• Integration and execution risk: The bank must integrate CIBC Caribbean’s businesses, systems, risk framework and culture across 10 countries, and the disclosure notes that integration could be more difficult, time-consuming or costly than expected, which may affect the timing and scale of projected synergies.
• Financing and leverage considerations: A portion of the cash consideration and related costs will be financed through about $700 million of Tier 2 subordinated debt, increasing leverage and introducing refinancing and interest-rate risk if market conditions change.
• Regulatory and closing uncertainty: Completion depends on Butterfield shareholder approval and numerous regulatory, governmental, securities exchange and exchange-control approvals. The filing highlights the possibility of delays, added conditions, or a failure to obtain approvals that could alter or prevent the transaction.
• Minority buyout and market reaction risk: The planned mandatory takeover bid and any follow-on compulsory acquisition processes for CIBC Caribbean minorities may be delayed or completed on different terms, and the documents flag potential reputational and business disruption risks around announcement, pendency and completion.

Insights

Banking M&A and Capital Analyst

Large, accretive Caribbean acquisition with strong capital but meaningful execution risk.

Butterfield is acquiring CIBC’s 91.7% stake in CIBC Caribbean for a total of $1.794 billion, split 61% cash and 39% shares. The transaction roughly doubles deposits to about $24.5 billion and grows assets to about $29 billion, significantly increasing the bank’s regional footprint and scale.

Management guides to 12% GAAP EPS accretion and 15% cash EPS accretion in the first full year with fully phased-in synergies, plus around 10% tangible book value per share accretion at closing. They target over $49 million in annual pre-tax cost savings by 2030 and an internal rate of return above 20%, while keeping the pro forma CET1 ratio above 12% and total capital above 19%.

Financing relies partly on $700 million of Tier 2 subordinated debt and the issuance of 11,577,367 new shares, which introduces leverage and dilution alongside the expected benefits. Integration across multiple jurisdictions, regulatory approvals, realization of synergies, and completion of the mandatory minority takeover bid are highlighted as key risks in the disclosure, so the eventual financial outcome will depend on execution over the years following the expected closing in the first half of 2027.

Key Figures

Total purchase price: $1.794 billion Cash consideration: $1.091 billion Share consideration: $703 million +5 more

8 metrics

Total purchase price $1.794 billion Aggregate consideration for 91.7% stake in CIBC Caribbean

Cash consideration $1.091 billion Cash portion of CIBC Caribbean purchase price

Share consideration $703 million Value of Butterfield shares issued, based on $55.66 VWAP

Exchange terms per CIBC Caribbean share $0.6918 cash + 0.008008 share Consideration for each CIBC Caribbean share held by CIBC’s holding company

New Butterfield shares issued 11,577,367 shares Ordinary shares issued to CIBC as part of consideration

Subordinated debt financing $700 million Tier 2 capital-qualifying subordinated notes to help fund cash portion

Expected GAAP EPS accretion 12% First full year after close with fully phased-in synergies

Target cost synergies $49 million per year Pre-tax run-rate savings expected by 2030

Key Terms

Tier 2 capital-qualifying subordinated debt, Common Equity Tier 1 (CET1) ratio, tangible book value per share accretion, mandatory take-over bid, +2 more

6 terms

Tier 2 capital-qualifying subordinated debt financial

"Butterfield has obtained commitments for $700 million of Tier 2 capital-qualifying subordinated debt financing"

A form of bank-issued debt that ranks below regular (senior) creditors but still counts toward the lender’s regulatory backup funds, called Tier 2 capital. Think of it as a secondary safety cushion that can absorb losses before depositors are hit; because it takes more risk, it usually pays higher interest, and changes to it can affect a bank’s perceived strength and share price, so investors treat it as riskier than senior bonds.

Common Equity Tier 1 (CET1) ratio financial

"the combined company is expected to maintain... a pro forma Common Equity Tier 1 (CET1) ratio above 12%"

The common equity tier 1 (CET1) ratio is a measure of a bank’s financial strength, showing how much high-quality capital it has compared to its risk-weighted assets. Think of it as a safety buffer or cushion that helps ensure the bank can withstand financial stress. A higher CET1 ratio indicates a stronger position, which is important for investors because it signals greater stability and resilience.

tangible book value per share accretion financial

"10% expected accretion to Butterfield’s tangible book value per share"

mandatory take-over bid regulatory

"the Company will commence a mandatory take-over bid for the remaining 8.33% of the CIBC Caribbean Shares held by minority shareholders"

A mandatory take-over bid is a regulator-enforced offer that a person or group must make to buy all remaining publicly traded shares of a company after they acquire control or cross a set ownership threshold. Think of it like buying most of an apartment building and being required to offer the same deal to the remaining tenants so everyone can choose to sell; it matters to investors because it can set or change the stock price, give minority holders a clear exit option, and determine who ultimately controls the company.

standstill obligations regulatory

"The Shareholder Agreement also includes customary standstill, voting, transfer and registration rights provisions and restrictions"

internal rate of return financial

"Internal rate of return of 20%+"

A percentage that represents the annualized yield an investment would earn, taking into account the timing and amount of all cash inflows and outflows; mathematically it is the rate that makes the discounted sum of future cash flows equal the initial cost. Investors use it to compare different projects or deals the way they compare interest rates — a higher internal rate of return suggests a stronger potential payoff, but it does not by itself show risk, scale, or timing nuances.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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FAQ

What acquisition did Butterfield (NTB) announce involving CIBC Caribbean?

Butterfield agreed to acquire CIBC’s 91.7% stake in CIBC Caribbean Bank Limited for a total of $1.794 billion, creating a combined bank with about $29 billion in assets across Bermuda, Cayman and multiple Caribbean markets, subject to shareholder and regulatory approvals.

How is the $1.794 billion purchase price for CIBC Caribbean structured?

The consideration totals $1.794 billion, or $1.14 per CIBC Caribbean share, split into $1.091 billion in cash and $703 million in Butterfield shares. Each CIBC Caribbean share held by CIBC’s holding company receives $0.6918 in cash plus 0.008008 Butterfield ordinary shares.

How will Butterfield finance the CIBC Caribbean acquisition?

Butterfield plans to fund part of the $1.091 billion cash component and related costs using $700 million of Tier 2 capital-qualifying subordinated debt. The remainder will come from existing resources, while $703 million of equity consideration will be paid in newly issued Butterfield ordinary shares.

What are the expected financial benefits of the CIBC Caribbean deal for NTB?

Management expects 12% GAAP EPS accretion and 15% cash EPS accretion in the first full year with fully phased-in synergies, 10% accretion to tangible book value per share at closing, an internal rate of return above 20%, and annual pre-tax cost savings of about $49 million by 2030.

How will the acquisition affect Butterfield’s capital ratios and balance sheet strength?

After closing and including new subordinated debt, the combined company is expected to have a pro forma Common Equity Tier 1 ratio above 12% and total capital above 19%. Management also cites a pro forma tangible common equity to tangible assets ratio of roughly 6% at closing.

What role will CIBC play in Butterfield after the transaction closes?

Following completion, CIBC is expected to own about 22% of Butterfield’s ordinary shares. Under a shareholder agreement, CIBC will initially be entitled to designate two directors to Butterfield’s board and will be subject to staged lock-up, standstill and customary registration rights provisions.

When is the Butterfield–CIBC Caribbean acquisition expected to close?

The transaction is targeted to close in the first half of 2027, assuming Butterfield shareholders approve the share issuance, all required regulatory and governmental consents are obtained, and customary closing conditions outlined in the share purchase agreement are satisfied or waived.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 6-K

REPORT OF FOREIGN PRIVATE ISSUER

PURSUANT TO RULE 13A-16 OR 15D-16

UNDER THE SECURITIES EXCHANGE ACT OF 1934

For the month of May 2026

Commission File Number: 001-37877

The Bank of N.T. Butterfield & Son Limited

(Translation of registrant’s name into English)

65 Front Street

Hamilton, HM 12

Bermuda

(Address of principal executive offices)

Indicate by check mark whether the registrant files or will file annual reports under cover Form 20-F or Form 40-F.

Form 20-F ý Form 40-F o

Indicate by check mark if the registrant is submitting the Form 6-K in paper as permitted by Regulation S-T Rule 101(b)(1): o

Indicate by check mark if the registrant is submitting the Form 6-K in paper as permitted by Regulation S-T Rule 101(b)(7): o

1

Entry into a Material Definitive Agreement

On May 27, 2026, The Bank of N.T. Butterfield & Son Limited (the “Company”), entered into a share purchase agreement (the “Purchase Agreement”) with Canadian Imperial Bank of Commerce (“CIBC”) and CIBC Investments (Cayman) Limited (“CICL” or “CIBC Holdco” and, together with CIBC, the “CIBC Parties”) providing for the acquisition of the CIBC Parties’ interest in CIBC Caribbean Bank Limited (“CIBC Caribbean”).

Pursuant to the terms of the Purchase Agreement, and upon the terms and subject to the conditions set forth therein, CIBC has agreed to sell, assign, transfer and deliver to the Company, and the Company has agreed to purchase and accept from CIBC, all of the issued and outstanding ordinary shares of CIBC Holdco (the “Share Purchase”). CIBC Holdco is the record owner of approximately 91.67% of the issued and outstanding common shares of CIBC Caribbean (the “CIBC Caribbean Shares”).

At the closing of the Share Purchase (the “Closing”), the Company will pay or issue to CIBC (or its applicable affiliate) aggregate consideration comprised of (i) 11,577,367 ordinary shares, par value BD$0.01 per share, of the Company (the “Ordinary Shares”), representing an exchange ratio of 0.008008 of an Ordinary Share for each CIBC Caribbean Share held by CIBC Holdco, and (ii) cash consideration of US$0.6918 for each CIBC Caribbean Share held by CIBC Holdco, subject to reduction for certain transaction expenses. On an aggregate basis and before any such deductions, the cash consideration would total US$1.091 billion (collectively, the “Purchase Price”). The Ordinary Shares issuable pursuant to the Purchase Agreement will be offered and sold in transactions not involving a public offering and will be issued in reliance on exemptions from the registration requirements of the Securities Act of 1933, as amended (the “Securities Act”).

In connection with the Share Purchase, the Company will commence a mandatory take-over bid for the remaining 8.33% of the CIBC Caribbean Shares held by minority shareholders (the “Takeover Bid”) in accordance with applicable law. CIBC Caribbean’s minority shareholders will be offered equivalent economic terms to CIBC and will also have the option to elect to receive up to 100% of their consideration in Ordinary Shares. To the extent permissible under applicable law, the Company plans to ultimately seek full ownership of CIBC Caribbean, including through any related compulsory acquisition, squeeze-out or similar process (the Takeover Bid and any such related transactions, collectively, the “Takeover Transactions”). Assuming CIBC Caribbean’s minority shareholders elect the same mix of cash and shares as CIBC, they are expected to collectively own approximately 2% of the Company.

The Purchase Agreement contains customary representations and warranties of the Company and the CIBC Parties, including representations and warranties relating to CIBC Caribbean made by the CIBC Parties, the parties have agreed to customary covenants, including, among others, covenants relating to (i) the conduct of their respective businesses during the period between the execution of the Purchase Agreement and the Closing, (ii) non-solicitation obligations relating to alternative acquisition proposals, and (iii) in the case of the Company, its obligation to call a meeting of its shareholders to approve the issuance of the Ordinary Shares in the Share Purchase and in connection with the Takeover Transactions (the “Company Share Issuance”) pursuant to applicable New York Stock Exchange (“NYSE”) listing rules. The parties have also agreed to use their reasonable best efforts to prepare and file all applications, notices and other documents to obtain all necessary consents and approvals for consummation of the transactions contemplated by the Purchase Agreement.

The completion of the Share Purchase is subject to customary conditions, including (i) approval by the Company’s shareholders of the Company Share Issuance, (ii) receipt of required regulatory approvals or non-objections, as applicable, (iii) authorization for listing on the NYSE and, to the extent required under applicable law or binding rule or regulation on the Bermuda Stock Exchange of the Ordinary Shares to be issued in the Company Share Issuance, and (iv) the absence of any order, injunction, decree or other legal restraint preventing the completion of the Share Purchase or any of the other transactions contemplated by the Purchase Agreement or making the completion of the Share Purchase or any such other transactions illegal. Each party’s obligation to complete the Share Purchase and the transactions contemplated by the Purchase Agreement is also subject to certain additional customary conditions including, subject to certain exceptions, the accuracy of the representations and warranties of the other party and performance in all material respects by the other party of its obligations under the Purchase Agreement.

The Purchase Agreement also includes covenants that will apply at or following the Closing relating to employee matters and maintenance of employee benefits, non-competition obligations of CIBC and its affiliates and reciprocal employee and customer non-solicitation obligations of the parties. The Purchase Agreement further contemplates that the Company and CIBC will enter into a transition services agreement at the Closing having a term of up to twenty-four (24) months, pursuant to which CIBC will provide certain transition services to the Company and CIBC Caribbean. In addition, the Purchase Agreement contemplates certain specific indemnification obligations of the parties, subject to limitations and procedures set forth in the Purchase Agreement.

2

The Company expects to finance a portion of the cash consideration and related fees and expenses through the issuance and sale of subordinated notes or other subordinated debt securities (the “Subordinated Debt Financing”). Under the Purchase Agreement, the CIBC Parties have agreed to use their reasonable best efforts, and cause CIBC Caribbean to use its reasonable best efforts, to provide customary cooperation and assistance to the Company in arranging, marketing and consummating the Subordinated Debt Financing.

The representations, warranties and covenants of each party set forth in the Purchase Agreement have been made only for purposes of, and were and are solely for the benefit of the parties to, the Purchase Agreement, may be subject to limitations agreed upon by the parties, including being qualified by confidential disclosures made for the purposes of allocating contractual risk between the parties instead of establishing these matters as facts, and may be subject to standards of materiality applicable to the parties that differ from those applicable to investors. Accordingly, the representations and warranties may not describe the actual state of affairs at the date they were made or at any other time, and investors should not rely on them as statements of fact.

Shareholder Agreement

In connection with the Closing, the Company and CIBC will enter into a shareholder agreement, substantially in the form attached as Exhibit A to the Purchase Agreement (the “Shareholder Agreement“), relating to CIBC’s ownership of Ordinary Shares following the Closing and other related matters. CIBC is expected to beneficially own approximately 22.3% of the Company’s issued and outstanding Ordinary Shares following completion of the Share Purchase.

The form of Shareholder Agreement provides that, subject to applicable law, stock exchange requirements, regulatory requirements and the Company’s governance policies, CIBC will have the right to designate two nominees to the Company’s Board of Directors depending on CIBC’s ownership percentage and to have CIBC-designated directors serve on specified committees of the Company’s Board of Directors. The Shareholder Agreement also includes customary standstill, voting, transfer and registration rights provisions and restrictions, including staged transfer restrictions on the Ordinary Shares issued to CIBC in the transaction, pursuant to which 25% of such Ordinary Shares will become transferable three months after Closing and an additional 25% will become transferable every six months thereafter, such that all such Ordinary Shares will become transferable twenty one (21) months after Closing, in each case subject to specified exceptions and restrictions. The Shareholder Agreement also provides for a 24.9% cap on CIBC’s beneficial ownership of Ordinary Shares, as well as customary shelf, demand and piggyback registration rights. The Shareholder Agreement will terminate immediately when the aggregate ownership percentage of CIBC and its affiliates ceases to be at least 5%.

The foregoing descriptions of the Purchase Agreement, the Share Purchase and the Shareholder Agreement and the other transactions contemplated thereby do not purport to be complete and are qualified in their entirety by reference to the full text of the Purchase Agreement, including the form of Shareholder Agreement attached as Exhibit A thereto, which are filed as Exhibits 2.1 and 10.1 hereto and incorporated herein by reference.

On May 28, 2026, the Company issued a press release announcing the execution of the Purchase Agreement. A copy of the press release is furnished as Exhibit 99.1 to this Form 6-K.

On May 28, 2026, the Company issued an investor presentation relating to the transaction contemplated by the Purchase Agreement. A copy of the investor presentation is furnished as Exhibit 99.2 to this Form 6-K.

3

FORWARD-LOOKING STATEMENTS

Certain of the statements made in this Form 6-K are forward-looking statements within the meaning of, and subject to the protections of, Section 27A of the Securities Act, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, and the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements are not historical facts and include statements with respect to, among other things, our beliefs, plans, objectives, goals, expectations, anticipations, assumptions, estimates, intentions, and future performance, including, without limitation statements regarding the proposed acquisition of CIBC Caribbean by Bank of N.T. Butterfield & Son Limited (“Butterfield”); the expected timing, structure, terms and completion of the proposed transaction; the expected form and mix of consideration, including the issuance of Butterfield ordinary shares; any acquisition of shares from minority shareholders of CIBC Caribbean or related compulsory acquisition, squeeze-out or similar process; the expected ownership, governance, management, capital, regulatory and operating profile of Butterfield following the proposed transaction; the expected financing of the proposed transaction, including the amount, terms and timing of the proposed subordinated debt financing; and the anticipated benefits of the proposed transaction, including expected scale, diversification, cost savings, synergies, earnings accretion, tangible book value per share accretion, capital generation, regulatory capital ratios, risk-weighted assets, liquidity, deposit mix, market position and other financial and operating impacts.

Forward-looking statements involve known and unknown risks, uncertainties and other factors, many of which are beyond Butterfield’s control, which may cause the actual results, performance, capital, ownership, financial condition or achievements of Butterfield to be materially different from future results, performance, capital, ownership, financial condition or achievements expressed or implied by such forward-looking statements. These risks and uncertainties include, among others: Butterfield’s ability to successfully complete the proposed acquisition of CIBC Caribbean on the anticipated terms or timeline or at all; Butterfield’s ability to realize the anticipated benefits of the proposed transaction in the expected timeframes or at all, including cost savings, synergies, balance sheet and capital optimization initiatives, earnings accretion, and tangible book value per share accretion; Butterfield’s ability to successfully integrate CIBC Caribbean’s businesses, operations, systems, controls, compliance programs, risk management framework, personnel and culture into those of Butterfield; the risk that such integration may be more difficult, time-consuming or costly than expected; the failure of any of the conditions to the proposed transaction to be satisfied or waived; the failure to obtain required shareholder, regulatory, governmental, securities exchange, exchange-control or other approvals, or delays in obtaining such approvals; the risk that such approvals may result in the imposition of conditions, restrictions or requirements that could adversely affect Butterfield, CIBC Caribbean or the expected benefits of the proposed transaction, potentially materially or that any proposed conditions, restrictions or requirements or; other actions of regulatory or governmental bodies or securities exchanges could delay or prevent the closing of the proposed transactions; the risk that any minority shareholder offer, compulsory acquisition, squeeze-out or similar process is delayed, not completed or completed on different terms than expected; revenues following the proposed transaction being lower than expected; operating costs, customer loss and business disruption, including difficulties in maintaining relationships with employees, customers, clients, depositors, vendors, suppliers, regulators and other business partners, being greater than expected; risks associated with the disruption of management’s attention from Butterfield’s ongoing business operations due to the proposed transaction; reputational risks and potential adverse reactions to the announcement, pendency or completion of the proposed transaction; the outcome of any legal, regulatory or shareholder proceedings, inquiries or investigations that may be instituted or arise in connection with the proposed transaction; the possibility that the proposed transaction may be more expensive to complete than anticipated, including as a result of unexpected transaction, integration, restructuring, financing, litigation, regulatory, tax, accounting or other costs; dilution caused by the issuance of additional Butterfield ordinary shares in connection with the proposed transaction; changes in Butterfield’s share price, interest rates, foreign exchange rates, capital markets or other market conditions that may affect the transaction financing or expected financial impacts of the proposed transaction; the risk that any subordinated debt or other transaction financing is not obtained on the expected terms, timing or at all; and the risk that assumptions underlying pro forma financial information, purchase accounting, credit marks, fair value marks, integration costs, cost savings, synergies, capital ratios, earnings accretion, tangible book value per share accretion, return metrics and other financial impacts prove to be inaccurate.

Other factors that may impact Butterfield’s future results, performance, financial condition or achievements include worldwide and regional economic conditions, including economic growth and general business conditions in Bermuda, the Cayman Islands, Barbados, The Bahamas, Turks and Caicos, Trinidad and Tobago, the broader Atlantic, Caribbean and other markets in which Butterfield or CIBC Caribbean operates; fluctuations in interest rates, inflation, monetary policy, foreign exchange rates, capital markets, tourism, real estate markets and sovereign credit ratings, including a decline in Bermuda’s sovereign credit rating; any sudden liquidity crisis; changes in customer behavior, including customer borrowing, repayment, investment and deposit practices; unfavorable developments concerning asset quality, credit quality, loan losses, non-performing loans, collateral values, loan concentrations, sovereign exposures, residential mortgage risk weighting, reserves, funding costs, liquidity and deposit flows; competitive product and pricing pressures; security risks, including cybersecurity, data privacy, fraud, financial crime, anti-money laundering and sanctions risks; the impact, extent and timing of technological changes, systems conversions and operational resilience initiatives; risks relating to the success of Butterfield’s updated systems and platforms; capital management activities; changes in laws, regulations, accounting standards, tax laws, regulatory capital or liquidity requirements and supervisory expectations; potential impacts of climate change, hurricanes and other natural disasters; compliance with regulatory requirements; and other factors.

4

Forward-looking statements can be identified by words such as "anticipate," "assume," "believe," "estimate," "expect," "indicate," "intend," "may," "plan," "point to," "predict," "project," "seek," "target," "potential," "will," "would," "could," "should," "continue," "contemplate" and other similar expressions, although not all forward-looking statements contain these identifying words. All statements other than statements of historical fact are statements that could be forward-looking statements.

All forward-looking statements in this Form 6-K are expressly qualified in their entirety by this cautionary notice, including, without limitation, those risks and uncertainties described in our SEC reports and filings, including under the caption "Risk Factors" in our most recent Form 20-F and in any subsequent reports furnished or filed with the Securities and Exchange Commission ("SEC"). Such reports are available upon request from Butterfield, or from the SEC including through the SEC’s website at https://www.sec.gov. Any forward-looking statements made by Butterfield is based only on information currently available and speaks only as of the date on which it is made. Except as otherwise required by law, Butterfield assumes no obligation and does not undertake to review, update, revise or correct any of the forward-looking statements included in this disclosure, whether as a result of new information, future events or other developments. You are cautioned not to place undue reliance on the forward-looking statements made by Butterfield in this disclosure. Comparisons of results for current and any prior periods are not intended to express any future trends or indications of future performance, and should only be viewed as historical data.

EXHIBIT INDEX

Exhibit						Description
2.1						Share Purchase Agreement, dated May 27, 2026, by and among The Bank of N.T. Butterfield & Son, Canadian Imperial Bank of Commerce and CIBC Investments (Cayman) Limited. †*
10.1						Form of Shareholder Agreement (included as Exhibit A to the Share Purchase Agreement).
99.1						Press Release - Butterfield Announces Agreement to Acquire Control of CIBC Caribbean
99.2						Investor Presentation - Butterfield Announces Agreement to Acquire Control of CIBC Caribbean

† Certain schedules have been omitted pursuant to Item 601(b)(2) of Regulation S-K. The registrant hereby undertakes to furnish supplementally copies of any of the omitted schedules upon request by the Securities and Exchange Commission.

* Certain personally identifiable information has been omitted from this exhibit pursuant to Item 601(a)(6) of Regulation S-K.

SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.

5

Date: May 28, 2026			THE BANK OF N.T. BUTTERFIELD & SON LIMITED
			By:			/s/ Michael Schrum
			Name:			Michael Schrum
			Title:			President & Group Chief Financial Officer

6

Butterfield Announces Agreement to Acquire Control of CIBC Caribbean in $1.8 Billion Transaction Transaction unites two premier, full-service banking and wealth management platforms with complementary experience in international financial centers and attractive Caribbean markets to create a $29 billion financial institution Hamilton, Bermuda and St. Michael, Barbados – May 28, 2026: The Bank of N.T. Butterfield & Son Limited (“Butterfield”) (NYSE: NTB | BSX: NTB.BH) has entered into a definitive agreement to acquire CIBC’s 91.7% interest in CIBC Caribbean Bank Limited (“CIBC Caribbean”), a relationship bank with a longstanding history serving communities across the Caribbean, to create a leading banking and wealth management platform in international financial centers and attractive Caribbean markets, with approximately $29 billion in assets. The transaction brings together two complementary banks with deep roots and established relationships across their combined footprint with heightened capacity, greater diversification and scalable growth to drive long-term value for all stakeholders. Butterfield and CIBC Caribbean’s expanded capabilities and scale are expected to provide enhanced corporate, personal and wealth management services across their combined client bases. Clients can expect greater ability to process cross- border payments, increased consumer and merchant banking capabilities, and continued investments in technology and digital banking infrastructure. Butterfield will maintain both organizations’ operational footprints, including CIBC Caribbean’s regional headquarters in Barbados, ensuring continuity for customers and employees. Butterfield is also committed to its and CIBC Caribbean’s philanthropic, financial education, and sustainability initiatives in each of their geographies, which will continue to provide outsized, tangible and mutually beneficial financial impacts for the combined company and its communities. Michael Collins, Butterfield’s Chairman and Chief Executive Officer, said: “Since Butterfield’s 2016 listing on the NYSE, we have successfully grown and enhanced profitability through bank and trust acquisitions. This deal combines two storied and complementary banks, with significant local scale advantages and time-honored customer relationships in their respective core jurisdictions. The transaction will offer both scale and diversification to the benefit of all stakeholders, positioning Butterfield as a leading independent bank and wealth manager operating across international financial centers and attractive Caribbean markets. I look forward to welcoming our talented new colleagues and valued clients.” Mark St. Hill, Chief Executive Officer of CIBC Caribbean, added: “For our clients, employees and communities, this combination brings together two organizations with shared values and a common focus on relationship banking, innovating and community impact. We look forward to building on our legacy as the region’s champion in financial services.” Harry Culham, President and CEO, CIBC, commented: "The entire CIBC Caribbean team led by Mark St. Hill has built a strong, client-focused bank across the region, and we look forward to realizing the strategic benefits of this transaction to deliver more for all stakeholders.” Transaction Details The total consideration to be paid for CIBC Caribbean will be comprised of $1,091 million in cash and $703 million in Butterfield shares valued by reference to Butterfield’s 10-day NYSE VWAP of $55.66 as of May 27, 2026, for an aggregate purchase price of $1,794 million, or $1.14 per CIBC Caribbean share.

2 Under the terms of the agreement, which have been unanimously approved by the Board of Directors of Butterfield, Butterfield will acquire CIBC Investments (Cayman) Limited, the holding company for CIBC’s 91.7% interest in CIBC Caribbean. Butterfield will subsequently commence a mandatory take-over bid for the remaining 8.3% of total outstanding shares of CIBC Caribbean held by minority shareholders, with the objective of acquiring full ownership of CIBC Caribbean, subject to applicable law and regulatory requirements. CIBC Caribbean’s minority shareholders will be offered equivalent economic terms as CIBC, and will also have the option to elect to receive up to 100% of their consideration in Butterfield shares, providing them with the opportunity to maintain the entirety of their investment in the combined organization, should they choose to do so. Houlihan Lokey, acting as financial advisor to the Special Committee of CIBC Caribbean’s Board of Directors, has provided an opinion to the Special Committee with respect to the fairness from a financial point of view of the consideration to be offered to CIBC Caribbean’s minority shareholders in the mandatory take-over bid. Assuming minority shareholders elect the same mix of cash and shares as CIBC, following completion of the take-over bid they would collectively own approximately 2% of Butterfield. In connection with the transaction, Butterfield has obtained commitments for $700 million of Tier 2 capital-qualifying subordinated debt financing expected to be raised prior to closing. Following completion of the transaction, the combined company is expected to maintain capital levels significantly above applicable regulatory thresholds on a consolidated basis, with a pro forma Common Equity Tier 1 (CET1) ratio above 12%, and total capital above 19% at closing. The transaction is expected to close in the first half of 2027, subject to receipt of Butterfield shareholder and regulatory approvals and the satisfaction of customary closing conditions. Following the transaction, Butterfield’s ordinary shares will continue to be listed on the New York Stock Exchange (NYSE) and the Bermuda Stock Exchange (BSX), and Butterfield intends to undertake additional secondary share listings on the Barbados Stock Exchange (BSE), the Bahamas International Securities Exchange (BISX), and the Trinidad & Tobago Stock Exchange (TTSE), subject to local listing and regulatory requirements. Following completion of the transaction, CIBC will own an approximately 22% stake in the combined entity. Under the terms of Butterfield and CIBC’s shareholder agreement, CIBC will then initially have the right to appoint two directors to Butterfield’s Board. The shareholder agreement will also provide for certain lockup restrictions with respect to CIBC’s stake in Butterfield, and include customary standstill obligations and registration rights. The Bermuda Monetary Authority (BMA) will continue to serve as the consolidated regulatory supervisor of Butterfield across all of its locations. Butterfield will also collaborate with all relevant jurisdictional authorities to ensure continuity, market confidence, and access to high-quality financial services within each jurisdiction. Financial Highlights • Total purchase price of $1,794 million, or $1.14 per CIBC Caribbean share, representing 106% of CIBC Caribbean’s tangible book value as of January 31, 2026 • Consideration is 61% cash ($1,091 million) and 39% ($703 million) Butterfield shares • Consideration per CIBC Caribbean share of $0.6918 in cash and 0.008008 in Butterfield shares based on the 10- day NYSE VWAP of $55.66 as of May 27, 2026 • Butterfield has obtained commitments for $700 million of Tier 2 capital-qualifying subordinated debt financing • Pro forma Common Equity Tier 1 (CET1) ratio above 12%, and total capital above 19% at closing • 12% expected accretion to GAAP EPS in year 1 with fully phased-in synergies, excluding integration costs • 15% expected accretion to cash EPS in year 1 with fully phased-in synergies, excluding integration costs, rate marks and transaction-related amortization • 10% expected accretion to Butterfield’s tangible book value per share • Internal rate of return of 20%+ • Pre-tax cost savings expected to reach an annual run rate of approximately $49 million once fully phased in by 2030

3 Advisors Barclays is serving as lead financial advisor to Butterfield, and Sullivan & Cromwell, Carey Olsen and Lex Caribbean are serving as legal advisors. BofA Securities is serving as financial advisor to Butterfield’s Board of Directors. H/Advisors is serving as communications advisor to Butterfield. Wachtell, Lipton, Rosen & Katz, Torys LLP and Chancery Chambers are serving as legal advisors to CIBC. CIBC Capital Markets is serving as financial advisor to CIBC Caribbean, and Mayer Brown LLP is serving as legal advisor. Houlihan Lokey is serving as financial advisor to the Special Committee of CIBC Caribbean’s Board of Directors. Finer Points Consultants is serving as communications advisor to CIBC Caribbean. Investor Call Butterfield will host a conference call for investors and analysts on Thursday, May 28, 2026 at 8:15 a.m. Eastern Time to discuss the transaction. Dial-in information: +1 (844) 855 9501 (toll-free US) or +1 (412) 858 4603 (international) Conference ID: Butterfield Group Live audio webcast: A live audio webcast of the call can be accessed via Butterfield’s investor relations page on Butterfield’s website at https://www.butterfieldgroup.com/investor-relations/events-presentations Replay: An audio replay of the call will be available at https://www.butterfieldgroup.com/investor-relations/events- presentations Website You can also learn more about today’s announcement at https://www.butterfieldgroup.com/future Forward-Looking Statements Certain of the statements made in this press release are forward-looking statements within the meaning of, and subject to the protections of, Section 27A of the Securities Act, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, and the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward- looking statements are not historical facts and include statements with respect to, among other things, our beliefs, plans, objectives, goals, expectations, anticipations, assumptions, estimates, intentions, and future performance, including, without limitation, statements regarding the proposed acquisition of CIBC Caribbean by Butterfield; the expected timing, structure, terms and completion of the proposed transaction; the expected form and mix of consideration, including the issuance of Butterfield ordinary shares; any acquisition of shares from minority shareholders of CIBC Caribbean or related compulsory acquisition, squeeze-out or similar process; the expected ownership, governance, management, capital, regulatory and operating profile of Butterfield following the proposed transaction; the expected financing of the proposed transaction, including the amount, terms and timing of the proposed subordinated debt financing; and the anticipated benefits of the proposed transaction, including expected scale, diversification, cost savings, synergies, earnings accretion, tangible book value per share accretion, capital generation, regulatory capital ratios, risk-weighted assets, liquidity, deposit mix, market position and other financial and operating impacts. Forward-looking statements involve known and unknown risks, uncertainties and other factors, many of which are beyond Butterfield’s control, which may cause the actual results, performance, capital, ownership, financial condition or achievements of Butterfield to be materially different from future results, performance, capital, ownership, financial condition or achievements expressed or implied by such forward-looking statements. These risks and uncertainties include, among others: Butterfield’s ability to successfully complete the proposed acquisition of CIBC Caribbean on the anticipated terms or timeline or at all; Butterfield’s ability to realize the anticipated benefits of the proposed transaction in the expected timeframes or at all, including cost savings, synergies, capital and balance sheet optimization initiatives, earnings accretion, and tangible book value per share accretion; Butterfield’s ability to successfully integrate CIBC Caribbean’s businesses, operations, systems, controls, compliance programs, risk management framework, personnel

4 and culture into those of Butterfield; the risk that such integration may be more difficult, time-consuming or costly than expected; the failure of any of the conditions to the proposed transaction to be satisfied or waived; the failure to obtain required shareholder, regulatory, governmental, securities exchange, exchange-control or other approvals, or delays in obtaining such approvals; the risk that such approvals may result in the imposition of conditions, restrictions or requirements that could adversely affect Butterfield, CIBC Caribbean or the expected benefits of the proposed transaction potentially materially or that any proposed conditions, restrictions or requirements or other actions of regulatory or governmental bodies or securities exchanges could delay or prevent the closing of the proposed transactions; the risk that any minority shareholder offer, compulsory acquisition, squeeze-out or similar process is delayed, not completed or completed on different terms than expected; revenues following the proposed transaction being lower than expected; operating costs, customer loss and business disruption, including difficulties in maintaining relationships with employees, customers, clients, depositors, vendors, suppliers, regulators and other business partners, being greater than expected; risks associated with the disruption of management’s attention from Butterfield’s ongoing business operations due to the proposed transaction; reputational risks and potential adverse reactions to the announcement, pendency or completion of the proposed transaction; the outcome of any legal, regulatory or shareholder proceedings, inquiries or investigations that may be instituted or arise in connection with the proposed transaction; the possibility that the proposed transaction may be more expensive to complete than anticipated, including as a result of unexpected transaction, integration, restructuring, financing, litigation, regulatory, tax, accounting or other costs; dilution caused by the issuance of additional Butterfield ordinary shares in connection with the proposed transaction; changes in Butterfield’s share price, interest rates, foreign exchange rates, capital markets or other market conditions that may affect the transaction financing or expected financial impacts of the proposed transaction; the risk that any subordinated debt or other transaction financing is not obtained on the expected terms, timing or at all; and the risk that assumptions underlying pro forma financial information, purchase accounting, credit marks, fair value marks, integration costs, cost savings, synergies, capital ratios, earnings accretion, tangible book value per share accretion, return metrics and other financial impacts prove to be inaccurate. Other factors that may impact Butterfield’s future results, performance, financial condition or achievements include worldwide and regional economic conditions, including economic growth and general business conditions in Bermuda, the Cayman Islands, Barbados, The Bahamas, Turks and Caicos, Trinidad and Tobago, the broader Atlantic, Caribbean and other markets in which Butterfield or CIBC Caribbean operates; fluctuations in interest rates, inflation, monetary policy, foreign exchange rates, capital markets, tourism, real estate markets and sovereign credit ratings, including a decline in Bermuda’s sovereign credit rating; any sudden liquidity crisis; changes in customer behavior, including customer borrowing, repayment, investment and deposit practices; unfavorable developments concerning asset quality, credit quality, loan losses, non-performing loans, collateral values, loan concentrations, sovereign exposures, residential mortgage risk weighting, reserves, funding costs, liquidity and deposit flows; competitive product and pricing pressures; security risks, including cybersecurity, data privacy, fraud, financial crime, anti-money laundering and sanctions risks; the impact, extent and timing of technological changes, systems conversions and operational resilience initiatives; risks relating to the success of Butterfield’s updated systems and platforms; capital management activities; changes in laws, regulations, accounting standards, tax laws, regulatory capital or liquidity requirements and supervisory expectations; potential impacts of climate change, hurricanes and other natural disasters; compliance with regulatory requirements; and other factors. Forward-looking statements can be identified by words such as "anticipate," "assume," "believe," "estimate," "expect," "indicate," "intend," "may," "plan," "point to," "predict," "project," "seek," "target," "potential," "will," "would," "could," "should," "continue," "contemplate" and other similar expressions, although not all forward-looking statements contain these identifying words. All statements other than statements of historical fact are statements that could be forward- looking statements. All forward-looking statements in this disclosure are expressly qualified in their entirety by this cautionary notice, including, without limitation, those risks and uncertainties described in our SEC reports and filings, including under the caption "Risk Factors" in our most recent Annual Report on Form 20-F and in any subsequent reports furnished or filed with the Securities and Exchange Commission ("SEC"). Such reports are available upon request from Butterfield, or from the SEC including through the SEC’s website at https://www.sec.gov. Any forward-looking statements made by Butterfield are current views as at the date they are made. Except as otherwise required by law, Butterfield assumes no obligation and does not undertake to review, update, revise or correct any of the forward-looking statements included in this disclosure, whether as a result of new information, future events or other developments. You are cautioned not to place undue reliance on the forward-looking statements made by Butterfield in this disclosure. Comparisons of results for current and any prior periods are not intended to express any future trends or indications of future performance, and should only be viewed as historical data. -ENDS-

5 About Butterfield: Butterfield is a full-service bank and wealth manager headquartered in Hamilton, Bermuda, providing services to clients from Bermuda, the Cayman Islands, Guernsey and Jersey, where our principal banking operations are located, and The Bahamas, Switzerland, Singapore and the United Kingdom, where we offer specialized financial services. Banking services comprise deposit, cash management and lending solutions for individual, business and institutional clients. Wealth management services are composed of trust, private banking, asset management and custody. In Bermuda, the Cayman Islands and Guernsey, we offer both banking and wealth management. In The Bahamas, Singapore and Switzerland, we offer select wealth management services. In the UK, we offer residential property lending. In Jersey, we offer select banking and wealth management services. Butterfield is publicly traded on the New York Stock Exchange (symbol: NTB) and the Bermuda Stock Exchange (symbol: NTB.BH). Further details on the Butterfield Group can be obtained from our website at: www.butterfieldgroup.com. BF-All About CIBC Caribbean: CIBC Caribbean is a relationship bank offering a full range of market leading financial services through our Corporate Banking, Personal and Business Banking and Private Wealth segments. CIBC Caribbean is located in ten (10) countries around the Caribbean, providing banking services through approximately 2,700 employees in 41 branches and offices. CIBC Caribbean also has a representative office in Hong Kong that provides business development and relationship management for its fund administration business. About CIBC: CIBC is a leading North American financial institution with 15 million personal banking, business, public sector and institutional clients. Across Personal and Business Banking, Commercial Banking and Wealth Management, and Capital Markets, CIBC offers a full range of advice, solutions and services through its leading digital banking network, and locations across Canada, in the United States and around the world. Investor Relations Contact: Media Relations Contact: Noah Fields Nicky Stevens Investor Relations Group Strategic Marketing & Communications The Bank of N.T. Butterfield & Son Limited The Bank of N.T. Butterfield & Son Limited Phone: (441) 299 3816 Phone: (441) 299 1624 E-mail: noah.fields@butterfieldgroup.com E-mail: nicky.stevens@butterfieldgroup.com CIBC Caribbean: Debra King Director of Corporate Communications CIBC Caribbean, Barbados Head Office E-mail: debra.king@cibccaribbean.com

1 May 28, 2026 Acquisition of CIBC Caribbean Bank Limited Creating a Leading Independent Banking Platform Investor Presentation May 28, 2026 (All values in US$ millions, unless otherwise stated)

2 May 28, 2026 Forward-Looking Statements: Certain of the statements made in this presentation are forward-looking statements within the meaning of, and subject to the protections of, Section 27A of the Securities Act, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended, and the safe harbor provisions of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements are not historical facts and include statements with respect to, among other things, our beliefs, plans, objectives, goals, expectations, anticipations, assumptions, estimates, intentions, and future performance, including, without limitation statements regarding the proposed acquisition of CIBC Caribbean Bank Limited (“CIBC Caribbean”) by The Bank of N.T. Butterfield & Son Limited (“Butterfield”); the expected timing, structure, terms and completion of the proposed transaction; the expected form and mix of consideration, including the issuance of Butterfield ordinary shares; any acquisition of shares from minority shareholders of CIBC Caribbean or related compulsory acquisition, squeeze-out or similar process; the expected ownership, governance, management, capital, regulatory and operating profile of Butterfield following the proposed transaction; the expected financing of the proposed transaction, including the amount, terms and timing of the proposed subordinated debt financing; and the anticipated benefits of the proposed transaction, including expected scale, diversification, cost savings, synergies, earnings accretion, tangible book value per share accretion, capital generation, regulatory capital ratios, risk-weighted assets, liquidity, deposit mix, market position and other financial and operating impacts. Forward-looking statements involve known and unknown risks, uncertainties and other factors, many of which are beyond Butterfield’s control, which may cause the actual results, performance, capital, ownership, financial condition or achievements of Butterfield to be materially different from future results, performance, capital, ownership, financial condition or achievements expressed or implied by such forward-looking statements. These risks and uncertainties include, among others: Butterfield’s ability to successfully complete the proposed acquisition of CIBC Caribbean on the anticipated terms or timeline or at all; Butterfield’s ability to realize the anticipated benefits of the proposed transaction in the expected timeframes or at all, including cost savings, synergies, capital optimization initiatives, earnings accretion, tangible book value per share accretion; Butterfield’s ability to successfully integrate CIBC Caribbean’s businesses, operations, systems, controls, compliance programs, risk management framework, personnel and culture into those of Butterfield; the risk that such integration may be more difficult, time-consuming or costly than expected; the failure of any of the conditions to the proposed transaction to be satisfied or waived; the failure to obtain required shareholder, regulatory, governmental, securities exchange, exchange-control or other approvals, or delays in obtaining such approvals; the risk that such approvals may result in the imposition of conditions, restrictions or requirements that could adversely affect Butterfield, CIBC Caribbean or the expected benefits of the proposed transaction; the risk that any minority shareholder offer, compulsory acquisition, squeeze-out or similar process is delayed, not completed or completed on different terms than expected; revenues following the proposed transaction being lower than expected; operating costs, customer loss and business disruption, including difficulties in maintaining relationships with employees, customers, clients, depositors, vendors, suppliers, regulators and other business partners, being greater than expected; risks associated with the disruption of management’s attention from Butterfield’s ongoing business operations due to the proposed transaction; reputational risks and potential adverse reactions to the announcement, pendency or completion of the proposed transaction; the outcome of any legal, regulatory or shareholder proceedings, inquiries or investigations that may be instituted or arise in connection with the proposed transaction; the possibility that the proposed transaction may be more expensive to complete than anticipated, including as a result of unexpected transaction, integration, restructuring, financing, litigation, regulatory, tax, accounting or other costs; dilution caused by the issuance of additional Butterfield ordinary shares in connection with the proposed transaction; changes in Butterfield’s share price, interest rates, foreign exchange rates, capital markets or other market conditions that may affect the transaction financing or expected financial impacts of the proposed transaction; the risk that any subordinated debt or other transaction financing is not obtained on the expected terms, timing or at all; and the risk that assumptions underlying pro forma financial information, purchase accounting, credit marks, fair value marks, integration costs, cost savings, synergies, capital ratios, earnings accretion, tangible book value per share accretion, return metrics and other financial impacts prove to be inaccurate. Other factors that may impact Butterfield’s future results, performance, financial condition or achievements include worldwide and regional economic conditions, including economic growth and general business conditions in Bermuda, the Cayman Islands, Barbados, The Bahamas, Turks and Caicos, Trinidad and Tobago, the broader Atlantic, Caribbean and other markets in which Butterfield or CIBC Caribbean operates; fluctuations in interest rates, inflation, monetary policy, foreign exchange rates, capital markets, tourism, real estate markets and sovereign credit ratings, including a decline in Bermuda’s sovereign credit rating; any sudden liquidity crisis; changes in customer behavior, including customer borrowing, repayment, investment and deposit practices; unfavorable developments concerning asset quality, credit quality, loan losses, non-performing loans, collateral values, loan concentrations, sovereign exposures, residential mortgage risk weighting, reserves, funding costs, liquidity and deposit flows; competitive product and pricing pressures; security risks, including cybersecurity, data privacy, fraud, financial crime, anti-money laundering and sanctions risks; the impact, extent and timing of technological changes, systems conversions and operational resilience initiatives; risks relating to the success of Butterfield’s updated systems and platforms; capital management activities; changes in laws, regulations, accounting standards, tax laws, regulatory capital or liquidity requirements and supervisory expectations; potential impacts of climate change, hurricanes and other natural disasters; compliance with regulatory requirements; and other factors. Forward-looking statements can be identified by words such as "anticipate," "assume," "believe," "estimate," "expect," "indicate," "intend," "may," "plan," "point to," "predict," "project," "seek," "target," "potential," "will," "would," "could," "should," "continue," "contemplate" and other similar expressions, although not all forward-looking statements contain these identifying words. All statements other than statements of historical fact are statements that could be forward-looking statements. All forward-looking statements in this disclosure are expressly qualified in their entirety by this cautionary notice, including, without limitation, those risks and uncertainties described in our SEC reports and filings, including under the caption "Risk Factors" in our most recent Annual Report on Form 20-F and in any subsequent reports furnished or filed with the Securities and Exchange Commission ("SEC"). Such reports are available upon request from Butterfield, or from the SEC including through the SEC’s website at https://www.sec.gov. Any forward-looking statements made by Butterfield are current views as at the date they are made. Except as otherwise required by law, Butterfield assumes no obligation and does not undertake to review, update, revise or correct any of the forward-looking statements included in this disclosure, whether as a result of new information, future events or other developments. You are cautioned not to place undue reliance on the forward-looking statements made by Butterfield in this disclosure. Comparisons of results for current and any prior periods are not intended to express any future trends or indications of future performance, and should only be viewed as historical data. About Non-GAAP Financial Measures: This presentation contains non-GAAP financial measures including “core” net income and other financial measures presented on a “core” basis. We believe such measures provide useful information to investors that is supplementary to our financial condition, results of operations and cash flows computed in accordance with GAAP; however, our non-GAAP financial measures have a number of limitations. In addition, these non-GAAP financial measures have no standardized meanings and are not defined by GAAP. As such, investors should not view these disclosures as a substitute for results determined in accordance with GAAP, and they are not necessarily comparable to non-GAAP financial measures that other companies use. Reconciliations of these non-GAAP measures to corresponding GAAP financial measures are provided in the Appendix of this presentation. Presentation of Financial Information: Certain monetary amounts, percentages and other figures included in this report have been subject to rounding adjustments. Accordingly, figures shown as totals in certain tables may not be the arithmetic aggregation of the figures that precede them, and figures expressed as percentages in the text may not total 100% or, as applicable, when aggregated may not be the arithmetic aggregation of the percentages that precede them. Forward-Looking Statements

3 May 28, 2026 1 Introduction and Strategic Rationale 2 Transaction Overview and Financial Impact 3 Due Diligence and Credit 5 Q&A Michael Collins Chairman and Chief Executive Officer The Bank of N.T. Butterfield & Son Limited Michael Schrum President and Group Chief Financial Officer The Bank of N.T. Butterfield & Son Limited Bri Hidalgo Group Chief Risk Officer The Bank of N.T. Butterfield & Son Limited Agenda Alexander Twerdahl SVP, Strategy and Corporate Development The Bank of N.T. Butterfield & Son Limited Presenters Topics for Discussion 4 Summary

4 May 28, 2026 Creating a Leading Independent Banking Platform Step Change in Scale(2) Source: Company disclosure. Note(s): Map not to scale. CIBC Caribbean financial statements are prepared in accordance with IFRS. Note(s): (1) As provided by The Banker. (2) Assuming completion of the transaction. (3) Consolidated FY2025 pro forma deposits as a % of Category A retail bank deposits as of Oct 31, 2025. (4) Butterfield’s FY2025 Bermuda deposits as a % of FY2025 total deposits of Butterfield Bermuda, HSBC Bermuda, Clarien Bank, and Bermuda Commercial Bank. (5) Current CIBC Caribbean HQ. (6) Business support centers. (7) Representative office. (8) Pro formas calculated as the sum of Butterfield and CIBC Caribbean Q1 2026 ending Mar 31 for Butterfield and Jan 31 for CIBC Caribbean, excluding the impact of purchase accounting; not prepared in accordance with Article 11 of Regulation S-X from the U.S. SEC. (9) Based on 2028E earnings with fully phased-in synergies, excluding integration costs and the impact of purchase accounting. (10) Measured at anticipated transaction close date of March 31, 2027. (11) Includes select independent banks and regional subsidiaries of global banks operating in the English-speaking Atlantic and Caribbean. Leading Bank in Attractive Markets Select Atlantic and Caribbean Banks by Total Assets (US$bn)(11) $29bn Total Assets(8) $25bn Total Deposits(8) Leading Bank in International Financial Centers and Attractive Caribbean Markets #1 Bermuda Bank(1) #1 Cayman Islands Bank(1) 50%+ Deposit Market Share(2,3) 30% Deposit Market Share(4) $1.7bn TCE(10) $400mm+ Run Rate Earnings(9) $29 $20 $19 $15 $14 $14 $10 $9 $7 P ro F or m a + R ep ub lic Fi na nc ia l N C B Ja m ai ca Sc ot ia ba nk C ar ib be an H SB C B er m ud a R B C C ar ib be an Fi rs t C it iz en s (T ri ni da d) The Bahamas Turks and Caicos Cayman Islands Jamaica British Virgin Islands St. Kitts Antigua St. Lucia Barbados Trinidad and Tobago Bermuda Legend CIBC Caribbean Existing Footprint Butterfield Existing Footprint Butterfield Current and Pro Forma Group HQ Pro Forma Regional HQ(5) Other International 6 Guernsey Jersey 6 Singapore Switzerland UK C ar ib be anHong Kong (7)

5 May 28, 2026 Complementary institutions with limited geographic overlap Shared vision of serving our combined clients and communities Leveraging the best of both for greater / more efficient investment in technology and cyber Continuity under stable regulatory structures Proven and experienced management team Transaction is aligned with the value creation strategy that Butterfield has executed against since its NYSE IPO in 2016 12% GAAP EPS accretion(1) and 15% cash EPS accretion(1,2) in the first full year 10% accretive to TBVPS at close(3,4) Attractive use of excess capital, generating 20%+ IRR and ~15% ROIC Well-capitalized, conservative balance sheet with 19%+ Total Capital Ratio at close(3) Pro forma ROATCE of ~20%(1) with the dividend rate to be maintained at $2.00 per year Adds a granular retail deposit base at an average cost of 85bps(5) Diversifies earnings mix, both geographically and by product, with a conservative approach to credit underwriting and risk Complementary Combination Financially Compelling and Resilient Combining Our Strengths With the Potential to Deliver Immediate Returns and Long-Term Value for All Stakeholders Note(s): (1) Based on 2028E earnings with fully phased-in synergies, excluding integration costs. (2) Excludes rate marks and transaction-related amortization. (3) Measured at anticipated transaction close date of March 31, 2027. (4) Compared to median consensus estimates. (5) For the fiscal year ending Oct 31, 2025.

6 May 28, 2026 $31.52 $28.58 $25.90 $23.52 $20.62 $19.01$18.22$17.67 $16.30 $14.89 2025202420232022202120202019201820172016 $5.60 $4.77$4.70 $4.33 $3.28 $3.04 $3.69$3.53 $2.86 $2.48 2025202420232022202120202019201820172016 Track Record of Value Creation Organically and Through M&A Note(s): Butterfield fiscal year ending Dec 31. Note(s): (1) Core Earnings per Share, TBVPS Excl. AOCI, Dividend Payout Ratio, and Total Payout Ratio are non-GAAP financial measures. For information regarding historical non-GAAP measures, including reconciliations, see Appendix D. Award-Winning Banking & Wealth Management Platform Core Earnings per Share(1) TBVPS Excl. AOCI(1) Proven Track Record of Scaling the Bank Through Acquisitions Dividend Payout Ratio: Total Payout Ratio: 33%36%37%40%53%58%47%42%44%28% 94%107%75%42%65%114%89%67%44%206% Trust & Corporate Services 2014 Corp. & Retail Banking of HSBC Bank (Cayman) 2014 Global Trust Solutions 2018 Channel Islands 2019 Trust Business 2022 Guernsey 2026 Trust Business of HSBC Bank (Bermuda) 2015

7 May 28, 2026 Transaction Overview and Financial Impact

8 May 28, 2026 Transaction Summary Synergies & Integration Structure & Consideration • CIBC Caribbean shareholders to receive $703mm in shares (39%) and $1,091mm in cash (61%)(2) • Pro Forma ownership of ~76% current Butterfield shareholders / ~22% Canadian Imperial Bank of Commerce (“CIBC”) / ~2% minority CIBC Caribbean shareholders(2) – Minority CIBC Caribbean shareholders (8.3% of CIBC Caribbean) to be offered equivalent economic terms in mandatory takeover bid and may elect to receive up to 100% of their consideration in Butterfield shares • Butterfield intends to issue $700mm in T2 Subordinated Debt in order to target a 19% Total Capital Ratio at close(3) • Closing of the transaction is subject to receipt of required regulatory approvals, Butterfield shareholder approval and other customary closing conditions(4) • Transaction expected to close in H1 2027 Transaction Value & Multiples • Complementary institutions with limited geographic overlap • ~$49mm in expected annual pre-tax cost synergies, phased in over 4 years – 10% of CIBC Caribbean’s non-interest expenses • Similar IT systems significantly reduces integration complexity and will enable more efficient long-term investment in technology and cyber • Butterfield will maintain both organizations’ operational footprints, including CIBC Caribbean’s regional headquarters in Barbados • A Transition Services Agreement (“TSA”) will be formalized pre-close to ensure continuity of services Board Composition & Management Approvals & Closing • Butterfield executive leadership team will be joined by 2 CIBC Caribbean executives • CIBC will have the right to nominate two directors to the Butterfield Board(4,5) – Shareholder Agreement to also include lockup and standstill obligations, as well as customary registration rights(5) • Total purchase price of $1,794 million, or $1.14 per CIBC Caribbean share(1) • Price / January 2026 Tangible Book Value of 1.06x • Price / 2025 Adjusted Earnings: 8.6x • Price / 2028 Earnings + After-Tax Fully Phased-In Cost Savings: 6.6x Note(s): CIBC Caribbean’s financial statements are prepared in accordance with IFRS. Note(s): (1) Based on Butterfield’s 10-day VWAP of $55.66 as at May 27, 2026. (2) CIBC holds 91.7% of the outstanding shares of CIBC Caribbean. Assumes pro rata shares and cash consideration to minority shareholders. (3) Measured at anticipated transaction close date of March 31, 2027. (4) Nominees are subject to applicable law and other requirements. (5) The terms and conditions of the Shareholder Agreement ("SHA") are described in Butterfield's Report on Form 6-K filed on May 28, 2026 with the SEC and the form of SHA is filed as an exhibit thereto.

9 May 28, 2026 Securities 42% Interest-Bearing Cash & Equiv. 26% Res. Mortgages 23% Commercial Loans 8% Personal Loans 1% Step Change in Scale and Diversification Demand 69% Term 31% Pro Forma(1) Demand 60% Term 28% Notice 12% Butterfield Standalone Net Interest Income 60% Fee Income 40% Securities 36% Interest-Bearing Cash & Equiv. 17% Res. Mortgages 21% Commercial Loans 22% Personal Loans 4% Other 0% Source: Company disclosure. Note(s): Pro formas calculated as the sum of Butterfield and CIBC Caribbean FY2025 ending Dec 31 for Butterfield and Oct 31 for CIBC Caribbean, excluding the impact of purchase accounting; not prepared in accordance with Article 11 of Regulation S-X from the U.S. SEC. CIBC Caribbean’s financial statements are prepared in accordance with IFRS. Note(s): (1) CIBC Caribbean segments include discontinued operations. (2) Adjusted for $56mm non-core FV loss on securities that will be retained by CIBC. Compelling Pro Forma Scale & Business Mix Significant increase in scale while maintaining a diversified business mix with stable fee-based revenue Granular, Low-Cost Retail Deposit Base Nearly doubles Butterfield’s deposit base, with a ~30bps reduction in cost of deposits while maintaining a favourable USD and USD-linked deposit mix Diversified Earning Assets Mix Meaningfully diversifies and expands Butterfield's earning assets, increasing expected yield on average earning assets Net Interest Income 66% Fee Income 34% 1.5% Cost of Deposits 1.2% Cost of Deposits 4.1% Yield on Average Earning Assets 4.8% Yield on Average Earning Assets 71% USD & USD-Linked Deposits 80% USD & USD-Linked Deposits $607mm 2025 Revenue $1.38bn 2025 Revenue(2) $12.7bn 2025 Deposits $24.5bn 2025 Deposits $13.5bn 2025 Earning Assets $25.3bn 2025 Earning Assets

10 May 28, 2026 Cayman 50% Bermuda 13% Channel Islands & UK 7% Other 2% Bahamas 11% Turks & Caicos 9% Barbados 8% Cayman 56%Bermuda 28% Channel Islands & UK 15% Other 1% Earnings Underpinned by Attractive Markets Source: Company disclosure. Note(s): Financial data as of FY2025, unless otherwise stated. CIBC Caribbean’s financial statements are prepared in accordance with IFRS. Note(s): (1) Adjusted for $56mm non-core FV loss on securities that will be retained by CIBC and other adjustments. (2) Excludes segments with net losses such as Trinidad & Tobago and Holdco & Eliminations, which total $13mm in total losses; Other – includes Bahamas & Cayman Trust and Jamaica from CIBC Caribbean and “Other” from both CIBC Caribbean and Butterfield. (3) Pro forma geographic earnings composition based on the total earnings exposure of Butterfield and CIBC Caribbean in FY2025. (4) Pro formas calculated as the sum of Butterfield and CIBC Caribbean FY2025 ending Dec 31 for Butterfield and Oct 31 for CIBC Caribbean, excluding the impact of purchase accounting; not prepared in accordance with Article 11 of Regulation S-X from the U.S. SEC. (5) Based on 2028E earnings with fully phased-in synergies, excluding integration costs and the impact of purchase accounting. ~70% of Butterfield’s pro forma earnings come from markets where it has an existing presence; new markets represent an attractive growth opportunity • ~70% of Butterfield’s pro forma earnings are from existing markets, with the Cayman Islands remaining as Butterfield’s primary source of earnings • The remaining ~30% of Butterfield’s pro forma earnings are primarily from three new international banking markets: – The Bahamas – Turks & Caicos Islands – Barbados • The transaction diversifies Butterfield’s geographic earnings mix and provides compelling growth opportunities as Butterfield enters attractive markets as a market leader Pro Forma Earnings Composition(1,2) $400mm+ Pro Forma Run-Rate Earnings(5) Butterfield Pro Forma Butterfield Standalone (3,4)

11 May 28, 2026 Compelling Fee Income Opportunity Source: Company disclosure. Note(s): Pro formas calculated as the sum of Butterfield and CIBC Caribbean FY2025 ending Dec 31 for Butterfield and Oct 31 for CIBC Caribbean, excluding the impact of purchase accounting; not prepared in accordance with Article 11 of Regulation S-X from the U.S. SEC. CIBC Caribbean’s financial statements are prepared in accordance with IFRS. Note(s): (1) Adjusted for $56mm non-core FV loss on securities that will be retained by CIBC. The combined platform provides a tangible opportunity to drive future fee income growth $67 $111 $179 $53 $81 $134 $123 $32 $155 $243 $225 $468 Butterfield CIBC Caribbean Pro Forma Banking Foreign Exchange Wealth Management FY2025 Fee Income• Butterfield will continue to execute towards a long-term fee income composition target of ~50% • Meaningfully increases Butterfield’s total fee income base – Stable, diversified fee income mix across banking, foreign exchange and wealth management – Adds significant scale to the wealth management business • The combined platform is anticipated to provide significant opportunities to expand future fee income, including: – Cross-selling wealth management products to CIBC Caribbean’s client base – Introduction of products across new markets • Although potential revenue synergies have been identified, they have not been incorporated into the financial modelling 40% 29% 34% Fee Income as a % of Revenue: (1)(1)

12 May 28, 2026 Financially Compelling with Enhanced Capital Generation Strong pro forma capital position at close, with the ability to generate significant retained earnings as a combined platform 12%+ CET1 Ratio Capital Levels At Close(1) 19%+ Total Capital Ratio Combined Profitability ~6% TCE / TA Note(s): (1) As of expected close, assumed to be March 31, 2027. (2) Based on 2028E earnings with fully phased-in synergies, excluding integration costs. (3) Excludes rate marks and transaction-related amortization. (4) Compared to median consensus estimates. (5) Assumes forecasted run-rate net income estimates for Butterfield and CIBC Caribbean, less financing / other costs and regular dividends based on current dividends per share on Butterfield pro forma share count. (6) Based on RWAs at close. Enhanced Capital Position and Generation 15% 2028E Cash EPS Accretion(2,3) ~20% 2028E ROATCE(2) 12% 2028E GAAP EPS Accretion(2) $300mm+ Net Organic Capital Generation(5) 10% TBVPS Accretion(1,4) ~250bps Run Rate Annual Capital Generation(5,6)

13 May 28, 2026 Due Diligence and Credit

14 May 28, 2026 Comprehensive Approach to Due Diligence Highlights Key Diligence Focus Areas • Robust, independently validated diligence supporting high confidence in risk and execution • Extensive, multi-disciplinary diligence across credit, financials, liquidity, operations, regulatory, and integration readiness • Review led by senior management with external specialist support, ensuring independent challenge across key technical areas • Deep, data-driven balance sheet analysis, including full loan/deposit tape review and loan-level testing of material exposures • Independent credit review covering over 80% of the corporate credit portfolio by value, supporting high confidence in asset quality and risk ratings • On-site diligence and direct management engagement, including operational walkthroughs and full access to documentation • Comprehensive review of funding, liquidity, capital, and CECL impacts, including FX and structural constraints Credit and Portfolio Operations Accounting / Tax Human Resources AML / Financial Crime / Compliance Capital / RWA / Stress / ICAAP ALCO / Liquidity Risk & Internal Audit Information Technology and Security Regulatory, Legal & Litigation

15 May 28, 2026 Track Record of Disciplined Underwriting Source: Company disclosure. Note(s): Financial data as of FY2025. CIBC Caribbean fiscal year ending Oct 31. CIBC Caribbean’s financial statements are prepared in accordance with IFRS. Note(s): (1) Business & sovereign asset class industry detail is based on exposure by industry group and includes some exposures that may be categorized otherwise. (2) CRE exposure consists of real estate and construction industry exposure, which is shown separately from the business & sovereign asset class. (3) Includes miscellaneous, agriculture, health & social work, education, recreational & community, fishing. (4) Other jurisdictions include Eastern Caribbean (10%), Jamaica (10%), Trinidad & Tobago (6%), Turks & Caicos (4%), British Virgin Islands (3%), and other (0%). CIBC Caribbean’s loan underwriting standards are consistent with Butterfield’s • Diversified, conservatively underwritten, and well performing loan portfolio • Low and stable historical loss experience • Conservative credit mark of 1.6x of closing reserves provides balance sheet protection CIBC Caribbean Loan Distribution(1) CIBC Caribbean Net Charge-Off Ratio 0.3% 0.1% 0.2% 0.6% 0.6% 0.1% 0.1% 2019 2020 2021 2022 2023 2024 2025 Sovereign 11% Distribution 7% Hospitality 7% Logistics & Comms 5% Utilities 5% Financial 4% Manufacturing 3%Mining & Quarrying 2% Other Business & Sovereign 46% Residential Mortgages 30% CRE 13% Personal 11% (2) 27% Bahamas 25% Cayman Islands 16% Barbados $7.7bn 2025 Gross Loans 33% Other Jurisdictions(4) (3) (2) Stable near-term credit performance, supported by sovereign-linked exposures and regulated infrastructure assets Stable NCOs post- COVID19

16 May 28, 2026 Summary

17 May 28, 2026 We Are Positioned for Durable Long-Term Success, With Benefits for All Stakeholders • Better product suite & capabilities • Connectivity across 19 operating jurisdictions, reducing the friction of doing international business • Scale to invest in technology and security • Improved wealth platform • Committed to branch & relationship banking • New growth markets with lower market shares • Continuity & proven regulatory structure • Supports sustainable economic growth • Community investment • Investment in financial wellness • Combined platform will continue to be a member of the UN Global Compact • Financially compelling transaction while maintaining a conservative, well-capitalized balance sheet • Scales franchise to ~$29bn in assets(1) with exposure to attractive markets providing for an enhanced long-term growth and capital generation profile • 2028E GAAP EPS accretion of 12%(2) and cash EPS accretion of 15%(2,3) • 10% TBVPS accretion at close(4) • NYSE-listed • Complementary cultures • Proven leadership team • Expanded core competencies • Opportunities for career development Customers Shareholders Employees Communities The combination of Butterfield and CIBC Caribbean is expected to enable us to better serve our customers, employees, communities, and drive enhanced shareholder value Note(s): (1) Pro formas calculated as the sum of Butterfield and CIBC Caribbean Q1 2026 ending Mar 31 for Butterfield and Jan 31 for CIBC Caribbean, excluding the impact of purchase accounting; not prepared in accordance with Article 11 of Regulation S-X from the U.S. SEC. (2) Based on 2028E earnings with fully phased-in synergies, excluding integration costs. (3) Excludes rate marks and transaction-related amortization. (4) Measured at anticipated transaction close date of March 31, 2027, compared to median consensus estimates.

18 May 28, 2026 Appendix A: Additional Financial Analysis

19 May 28, 2026 Transaction Assumptions • Total purchase price of $1,794mm, or $1.14 per CIBC Caribbean share – $703mm (39%) in Shares / $1,091mm (61%) in Cash – Butterfield shares valued by reference to Butterfield’s 10-day VWAP of $55.66 per share as of May 27, 2026 • CIBC Caribbean shareholders will receive 0.008008 Butterfield shares and $0.6918 in cash for each CIBC Caribbean share • Issuance of $700mm of Tier 2 Subordinated Debt – Butterfield has obtained commitments for $700mm of Tier 2 Subordinated Debt • CIBC Caribbean projections based on detailed due diligence and informed by CIBC Caribbean management forecast • Butterfield projections based on consensus estimates through 2027, with assumed 2.5% earnings growth in 2028 • Pre-tax annual cost savings of $49 million, expected to be fully achieved by 2030 – 10.0% of CIBC Caribbean estimated 2027 non-interest expense; 5.5% of combined 2027 non-interest expense – Phased in 25%/50%/75%/100% in 2027/2028/2029/2030 and 100% thereafter • Accelerated impact of OECD Pillar Two Global Minimum Tax (15%) • Total one-time expenses of $175mm pre-tax (9.8% of deal value) – $91mm pre-tax (5.1% of deal value) expensed 50%/25%/25% in 2027/2028/2029 – $84mm pre-tax (4.7% of deal value) expensed at closing • Assumes early adoption of FASB’s amendments to ASU 2016-13, eliminating non-PCD credit mark and related “double-count" • Gross credit mark of ~4.4% of CIBC Caribbean’s estimated gross loans at close ($348mm, ~1.58x closing reserves)(1) • Non-credit loan fair value mark-down of $40mm accreted straight line over ~6 years • Non-credit HTM securities fair value mark-up of $7mm amortized straight line over ~5 years • Other net fair value mark-up to equity of $43mm related to real estate and deposits • Assumed close date of March 31, 2027 • CDI equal to ~3.0% of core deposits(2) amortized straight-line over 15 years Consideration Tier 2 Subordinated Debt One-Time Expenses Credit Mark Earnings Forecast Other Items Corporate Income Tax Note(s): (1) Includes the impact of transitioning loan reserves to GAAP accounting standards. (2) January 31, 2026. Other Pre-Tax Fair Value Marks Cost Savings

20 May 28, 2026 Pro Forma Financial Impact Note(s): (1) Based on 2028E earnings with fully phased-in synergies, excluding integration costs. (2) Excludes rate marks and transaction-related amortization. (3) As of May 27, 2026. 2028 Earnings per Share Reconciliation 2028 Earnings per Share Reconciliation Butterfield Standalone Net Income (Estimate) $258 CIBC Caribbean Standalone Net Income (Estimate) 230 After-Tax Transaction Adjustments Fully Phased-In Post-Tax Cost Savings $42 Accretion from Interest Rate Marks 5 New CDI Intangible Amortization (17) Transaction Funding, Incremental Corporate Tax, & Other Costs (101) Butterfield Pro Forma Net Income $417 Butterfield Pro Forma EPS(1) $7.83 Butterfield Standalone EPS $7.02 2028 GAAP EPS Accretion to Butterfield ($)(1) $0.82 2028 GAAP EPS Accretion to Butterfield (%)(1) 11.6% Butterfield Pro Forma Cash EPS(1,2) $8.09 Butterfield Standalone Consensus EPS $7.02 2028 Cash Accretion to Butterfield ($)(1,2) $1.07 2028 Cash Accretion to Butterfield (%)(1,2) 15.3% First full year of combined operations Tangible Book Value per Share Reconciliation Consensus TBVPS (Q1 2027)(3) $30.03 Butterfield Standalone Common Equity at Closing $1,307 Stock Consideration 703 Other Adjustments 123 Pro Forma Common Equity at Closing $2,133 Pro Forma Intangibles at Closing 410 Pro Forma Tangible Common Equity at Closing $1,722 Butterfield Standalone Shares Outstanding at Closing (mm) 39.3 Butterfield Shares Issued to CIBC Caribbean Shareholders (mm) 12.6 Pro Forma Common Shares Outstanding (mm) 52.0 Pro Forma Tangible Book Value per Share $33.15 TBVPS Accretion vs. Consensus 10.4%

21 May 28, 2026 Appendix B: CIBC Caribbean and Select Jurisdiction Overview

22 May 28, 2026 Overview of CIBC Caribbean’s Operating Jurisdictions Source: S&P Capital IQ, Government Websites, United Nations Department of Economic and Social Affairs, Moody’s Analytics, U.S. International Trade Administration. Note(s): Economic statistics as of most recently available. Deposit Market Share calculated based on CIBC Caribbean’s total deposits per jurisdiction as a % of system deposits. The Bahamas $16.6bn Nominal GDP ~400k Population ~20% Deposit Market Share Capital: Nassau Official Language: English Currency: Bahamian Dollar (BSD/USD pegged: 1.0) Government: Parliamentary Democracy (Constitutional Monarchy) Cayman Islands $8.2bn Nominal GDP ~74k Population ~20% Deposit Market Share Capital: George Town Official Language: English Currency: Cayman Islands Dollar (KYD/USD pegged: 1.2) Government: Parliamentary Democracy (British Overseas Territory) Barbados $8.0bn Nominal GDP ~282k Population ~35% Deposit Market Share Capital: Bridgetown Official Language: English Currency: Barbadian Dollar (BBD/USD pegged: 0.5) Government: Parliamentary Republic Turks & Caicos $1.7bn Nominal GDP ~46k Population 50%+ Deposit Market Share Capital: Cockburn Town Official Language: English Currency: USD Government: Parliamentary Democracy (British Overseas Territory) Jamaica $22.3bn Nominal GDP ~2.8mm Population 5%+ Deposit Market Share Capital: Kingston Official Language: English Currency: Jamaican Dollar (JMD/USD: ~0.0063) Government: Parliamentary Democracy (Constitutional Monarchy) Trinidad & Tobago $25.7bn Nominal GDP ~1.5mm Population ~3% Deposit Market Share Capital: Port of Spain Official Language: English Currency: Trinidad & Tobago Dollar (TTD/USD: ~0.15) Government: Parliamentary Republic Antigua & Barbuda $2.2bn Nominal GDP ~94k Population ~25% Deposit Market Share Capital: St. John’s Official Language: English Currency: Eastern Caribbean Dollar (XCD/USD pegged: 0.37) Government: Parliamentary Democracy (Constitutional Monarchy) St. Kitts & Nevis $1.1bn Nominal GDP ~47k Population 5%+ Deposit Market Share Capital: Basseterre Official Language: English Currency: Eastern Caribbean Dollar (XCD/USD pegged: 0.37) Government: Federal Parliamentary Democracy St. Lucia $2.7bn Nominal GDP ~180k Population 20%+ Deposit Market Share Capital: Castries Official Language: English Currency: Eastern Caribbean Dollar (XCD/USD pegged: 0.37) Government: Parliamentary Democracy (Constitutional Monarchy) British Virgin Islands $1.8bn Nominal GDP ~39k Population 15%+ Deposit Market Share Capital: Road Town Official Language: English Currency: USD Government: Parliamentary Democracy (British Overseas Territory)

23 May 28, 2026 $543 $577 $715 $747 $764 $137 $184 $261 $278 $208 $363 $379 $512 $541 $540 $180 $198 $204 $206 $225 2021 2022 2023 2024 2025 Net Interest IncomeFee Income Adj. NI to Common Overview of CIBC Caribbean Historical Financial PerformanceCompany Overview CIBC Caribbean is an important full-service banking institution in several international financial centers, offering Corporate Banking, Personal and Business Banking, and Wealth Management services Physical presence in 10 countries in the Western Atlantic and Caribbean, ~2,700 employees provide banking services in 42 branches, serving ~530k clients CIBC Caribbean is one of the oldest banks in the region with a strong global bank heritage – Formed in 2002 through the merger of CIBC West Indies Holdings and Barclays Bank’s Caribbean operations – In Dec 2006, CIBC acquired Barclays’ stake and became the majority shareholder in CIBC Caribbean Source: Company disclosure, IMF World Economic Outlook Database. Note(s): CIBC Caribbean’s financial data is prepared in accordance with IFRS and as of FY2025, unless otherwise stated. CIBC Caribbean fiscal year ending Oct 31. Note(s): (1) Consolidated Cayman Islands bank and trust. (2) Includes Antigua, St. Lucia, St. Kitts, and Trinidad & Tobago. (3) Adj. NI to Common, Adj. ROATCE, Adj. ROAA are non-IFRS financial measures. For information regarding historical non-IFRS measures, including reconciliations, see Appendix D. (4) Adjusted for $56mm non-core FV loss on securities that will be retained by CIBC. (5) Does not include overdrafts. (6) Restated under Basel III framework. Significant Scale Across Key Markets Cayman Islands $2.1bn Loans(1) $3.0bn Deposits(1) The Bahamas $2.0bn Loans $2.7bn Deposits Barbados $1.2bn Loans $2.1bn Deposits Turks & Caicos Islands $0.3bn Loans $1.3bn Deposits Jamaica $0.8bn Loans $0.9bn Deposits Eastern Caribbean and Other(2) $1.2bn Loans $1.4bn Deposits Well-Capitalized with a Strong Financial Profile Deposit Franchise 50% Non-Interest Bearing Deposits ~$21,000 Avg. Deposit Size(5) 0.85% Cost of Deposits Loan Portfolio 6.4% Yield on Loans 46% Business & Sovereign Loans 30% Residential Mortgages Capital(6) 16.7% Tier 1 Capital 17.8% Total Capital Ratio $1.6bn Total Capital Balance Sheet $13.8bn Assets $11.8bn Deposits $7.7bn Gross Loans Profitability 13.0% Adj. ROATCE(3) 1.5% Adj. ROAA(3) 4.1% Net Interest Margin (4) Adj. ROATCE: 14% 17% 22% 20% 13%(3) (3)

24 May 28, 2026 Solidifying Butterfield’s Position as the #1 Cayman Islands Bank Source: Company disclosure, Cayman Islands Monetary Authority, Moody’s, S&P. Note(s): Pro formas calculated as the sum of Butterfield and CIBC Caribbean FY2025 ending Dec 31 for Butterfield and Oct 31 for CIBC Caribbean, excluding the impact of purchase accounting; not prepared in accordance with Article 11 of Regulation S-X from the U.S. SEC. CIBC Caribbean’s financial statements are prepared in accordance with IFRS. Note(s): (1) Consolidated FY2025 pro forma deposits as a % of Category A retail bank deposits as of Oct 31, 2025. (2) Butterfield’s consolidated Cayman Islands segment. (3) Pro forma includes Butterfield’s Cayman Islands segment and CIBC Caribbean’s consolidated Cayman Islands bank and trust. Highly Attractive Market CIBC Caribbean’s operations in the Cayman Islands are highly complementary, bolstering scale in one of Butterfield’s most important markets Enhanced Deposit Leadership ($bn) Rank Bank Total Deposits PF Butterfield (Cayman) $7.1 1 Butterfield (Cayman) $4.1 2 CIBC Caribbean (Cayman) $3.0 3 Cayman National Bank Ltd. $2.1 4 Scotiabank & Trust (Cayman) Ltd. $1.9 5 RBC Royal Bank (Cayman) Limited $0.9 + The Cayman Islands is one of Butterfield’s core banking markets • Steadily expanding economy • Leading international financial center for insurers and funds, with 80%+ of the world’s offshore hedge funds and ~$8tn of investment fund AUM • Stable political and social environment underpinned by an Aa3 Moody’s sovereign credit rating Complementary Loan Mix Res. Mortgages 58%Business & Gov. 22% Other Mortgages 14% Personal Loans 6% Res. Mortgages 46% Business & Gov. 41% Other Mortgages 6% Personal Loans 7% Butterfield Pro-Forma Butterfield Standalone $3.2bn Pro Forma 2025 Loans(3) $1.0bn Standalone 2025 Loans(2) 50%+ Pro Forma Deposit Market Share(1) The combination of Butterfield and CIBC Caribbean reinforces Butterfield’s leadership in Cayman Islands deposits and lending

25 May 28, 2026 Additionally Establishes Butterfield as the #1 Bank in The Bahamas, Barbados and Turks & Caicos Source: Company disclosure, Central Bank of the Bahamas, Central Bank of Barbados, TCI Statistics Authority, S&P Capital IQ. CIBC Caribbean fiscal year ending Oct 31. Excludes impact of purchase accounting. Note(s): Pro formas calculated as the sum of Butterfield and CIBC Caribbean FY2025 ending Dec 31 for Butterfield and Oct 31 for CIBC Caribbean, excluding the impact of purchase accounting; not prepared in accordance with Article 11 of Regulation S-X from the U.S. SEC. CIBC Caribbean’s financial statements are prepared in accordance with IFRS. Note(s): (1) Includes CIBC Caribbean’s consolidated Bahamas and Barbados operations. Antigua, St. Kitts, St. Lucia, and Turks & Caicos based on branch financials. (2) CIBC Caribbean’s FY2025 Bahamas deposits as a % of domestic bank deposits (including non-resident deposits) as of Oct 31, 2025. (3) CIBC Caribbean’s FY2025 Barbados deposits as a % of commercial bank deposits, excluding deposits with the Central Bank or other depository corporations as of Oct 31, 2025. (4) CIBC Caribbean’s FY2025 Turks & Caicos deposits as a % of domestic bank deposits (including non-resident deposits) as of Oct 31, 2025. CIBC Caribbean is the market leader with a long history of relationship banking in well established markets ~20% The Bahamas Deposit Market Share(2) High Quality Deposit Base(1) Diversified Loan Mix(1) ~35% Barbados Deposit Market Share(3) $7bn+ Total 2025 Deposits $4bn+ Total 2025 Loans Expansion in Attractive Growth Markets The Bahamas • ~$17bn 2025 GDP • Well-established financial center for international banking and wealth management with ~700+ investment funds • Tourism sector provides growth and development tailwinds 50%+ Turks & Caicos Deposit Market Share(4) Barbados • ~$8bn 2025 GDP • Regional hub for financial services businesses in the Caribbean • Emerging international financial center with a stable, well-regulated banking market Turks & Caicos • ~$2bn 2025 GDP • Strong services and tourism-led economy with consistent growth • British Overseas Territory • USD market with no exchange controls • A- rated market by S&P Bahamas 38% Barbados 43% Turks & Caicos 19% Jurisdiction Demand 63% Notice 23% Term 14% Type Bahamas 46% Barbados 46% Turks & Caicos 7% Jurisdiction Corporate Loans 50% Residential Mortgages 34% Personal Loans 10% Other 5% Segment

26 May 28, 2026 Appendix C: Commitment to Communities

27 May 28, 2026 Better Serving Our Communities The transaction establishes a financial institution that is well positioned to serve communities in the Atlantic and Caribbean • Independent financial institution offering connectivity across 19 operating jurisdictions – Reduces the friction of doing international business and enhances international financial mobility in the Atlantic and Caribbean • Well-capitalized banking institution with enough scale to support local businesses, increase access to everyday banking for individuals, and finance important projects – Proven regulatory and governance structure supports regional banking system stability – Improved access to and depth of banking products for customers • Coordinated investments in technology and fraud prevention to provide better services to our customers – Improvements to our quality of service – Expanded offering of digital services • Committed to the communities we serve, offering scholarships, internships, charitable giving, and skill development programs – Deeply invested in the success of the jurisdictions where we operate, and is focused on delivering programs that have a positive impact Highly complementary banks with an enhanced range of products across markets

28 May 28, 2026 Appendix D: Reconciliations

29 May 28, 2026 Non-GAAP Reconciliation – Butterfield For the year ended December 31 2025 2024 2023 2022 2021 2020 2019 2018 2017 2016 Reconciliation of net income (GAAP) to core net income (non-GAAP) Net income A $231.9 $216.3 $225.5 $214.0 $162.7 $147.2 $177.1 $195.2 $153.3 $115.9 Less: Dividends and guarantee fee for preference shares B - - - - - - - - - (15.7) Less: Premium paid on repurchase/redemption of preference shares C - - - - - - - - - (41.9) Net income to common shareholders D = A - B - C $231.9 $216.3 $225.5 $214.0 $162.7 $147.2 $177.1 $195.2 $153.3 $58.4 Non-core (gains), losses and expenses Non-core (gains) losses Liquidation settlement from an investment previously written-off - - ($4.0) - - - - - - - Gain on disposal of Visa Inc. Class B shares - - - - (0.9) - - - - - Distribution from equity method investment - - - - - (0.7) - - - - Gain on disposal of a pass-through note investment (formerly a SIV) - - - - - - (1.0) (1.2) (2.6) (0.6) Settlement loss on de-risking on a defined benefit plan - - - - - - - 1.5 - - Adjustment to holdback payable for previous business acquisitions - - - - - - - - 0.1 0.9 Total non-core (gains) losses E - - ($4.0) - ($0.9) ($0.7) ($1.0) $0.3 ($2.5) $0.3 Non-core expenses Early retirement program, redundancies and other non-core compensation costs $5.5 $1.5 $7.9 $1.0 $1.5 $8.0 $16.3 - $0.2 $1.8 Tax compliance review costs - 0.3 0.1 0.4 0.2 - - 0.5 2.1 1.6 Asset / business acquisition costs - - 1.9 - - - 5.5 1.0 2.0 3.2 Restructuring charges and related professional service fees - 0.8 0.2 - - - - - 1.8 6.3 Provision in connection with ongoing tax compliance review - - - 0.2 0.1 - - - - 0.7 Secondary offering costs - - - - - - - - 2.0 - Cost of 2010 legacy option plan vesting and related payroll taxes - - - - - - - - - 8.8 Total non-core expenses F $5.6 $2.6 $10.0 $1.7 $1.8 $8.0 $21.8 $1.5 $8.1 $22.4 Total non-core (gains), losses and expenses G = E + F $5.6 $2.6 $6.0 $1.7 $0.9 $7.3 $20.8 $1.8 $5.6 $22.7 Core net income H = A + G $237.5 $218.9 $231.5 $215.7 $163.6 $154.5 $197.9 $197.0 $158.9 $138.6 Core net income attributable to common shareholders I = D - C + G $237.5 $218.9 $231.5 $215.7 $163.6 $154.5 $197.9 $197.0 $158.9 $123.0

30 May 28, 2026 Non-GAAP Reconciliation – Butterfield (cont’d) For the year ended December 31 2025 2024 2023 2022 2021 2020 2019 2018 2017 2016 Reconciliation of dividend payout ratio Dividends paid J $77.7 $79.6 $86.2 $87.3 $87.3 $88.9 $93.6 $83.7 $69.7 $34.0 Dividend payout ratio (based on core net income) J / I 32.7% 36.4% 37.2% 40.5% 53.4% 57.6% 47.3% 42.5% 43.9% 27.6% Repurchase of common/preferred stock K $146.7 $155.3 $88.6 $3.9 $19.8 $86.6 $81.5 $48.4 - $219.3 Total payout L = J + K $224.4 $234.9 $174.8 $91.2 $107.0 $175.6 $175.2 $132.1 $69.7 $253.3 Total payout ratio (based on core net income) L / I 94.5% 107.3% 75.5% 42.3% 65.4% 113.6% 88.5% 67.1% 43.9% 205.9% Reconciliation of diluted earnings per share (GAAP) to core earnings per common share fully diluted (non-GAAP) Core earnings per common share fully diluted Adjusted weighted average number of diluted common shares (in millions) M 42.4 45.9 49.3 49.9 49.9 50.9 53.7 55.7 55.5 49.6 Earnings per common share fully diluted N = D / M $5.47 $4.71 $4.58 $4.29 $3.26 $2.90 $3.30 $3.50 $2.76 $1.18 Non-core items per share O = (F - C) / M $0.13 $0.06 $0.12 $0.04 $0.02 $0.14 $0.39 $0.03 $0.10 $1.30 Core earnings per common share fully diluted N + O $5.60 $4.77 $4.70 $4.33 $3.28 $3.04 $3.69 $3.53 $2.86 $2.48 Tangible book value per common share Shareholders' equity P $1,141.9 $1,020.8 $1,003.6 $864.8 $977.5 $981.9 $963.7 $882.3 $822.9 $710.7 Less: goodwill and intangible assets Q (86.8) (89.6) (98.9) (74.4) (86.1) (92.8) (96.5) (74.7) (60.6) (61.9) Tangible common equity R = P - Q $1,055.1 $931.2 $904.7 $790.4 $891.4 $889.1 $867.2 $807.6 $762.3 $648.8 Basic participating shares outstanding (in millions) S 39.9 42.9 46.9 49.7 49.3 49.4 52.4 54.1 54.7 53.3 Tangible book value per common share R / S $26.41 $21.70 $19.29 $15.92 $18.08 $18.00 $16.55 $14.93 $13.94 $12.18 Tangible common equity R $1,055.1 $931.2 $904.7 $790.4 $891.4 $889.1 $867.2 $807.6 $762.3 $648.8 Plus: Accumulated other comprehensive loss T 204.2 295.2 310.2 377.5 124.9 49.7 87.1 148.5 129.1 144.7 Tangible book value per common share excl. accumulated other comprehensive loss (R + T) / S $31.52 $28.58 $25.90 $23.52 $20.62 $19.01 $18.22 $17.67 $16.30 $14.89

31 May 28, 2026 Non-IFRS Reconciliation – CIBC Caribbean Source: Company disclosure. CIBC Caribbean fiscal year ending Oct 31. CIBC Caribbean’s financial statements are prepared in accordance with IFRS. For the year ended October 31 2025 2024 2023 2022 2021 Reconciliation of net income (IFRS) to adjusted net income (non-IFRS) Net income A $160 $278 $270 $176 $126 Less: Non-controlling interests B (5) (7) (6) (3) (4) Net Income to common C = A - B $154 $271 $264 $173 $122 Adjustments FV loss related to non-core investment 56 - - - - Net gain (loss) related to divestitures (2) - (3) - - Net expenses related to announced divestitures - 8 - - - Provisions related to announced divestitures - - - 11 5 Restructuring charge - - - - 10 Income tax credit - - - - (1) Total adjustments D 54 8 (3) 11 14 Adjusted net income E = A + D $214 $285 $267 $187 $140 Adjusted net income to common F $208 $278 $261 $184 $137 Reconciliation of return on average common equity (IFRS) to adj. return on average tangible common equity (non-IFRS) Average common equity G 1,647 1,456 1,225 1,126 1,050 Less: average goodwill and intangible assets H (44) (44) (44) (44) (44) Average tangible common equity I = G - H 1,603 1,412 1,180 1,081 1,006 Return on average common equity C / G 9.4% 18.6% 21.6% 15.3% 11.6% Adjusted return on average tangible common equity F / I 13.0% 19.7% 22.1% 17.0% 13.6% Reconciliation of return on average assets (IFRS) to adj. return on average assets (non-IFRS) Average total assets J $13,571 $12,915 $12,826 $12,993 $12,517 Return on average assets C / J 1.1% 2.1% 2.1% 1.3% 1.0% Adjusted return on average assets F / J 1.5% 2.2% 2.0% 1.4% 1.1%

32 May 28, 2026 Appendix E: Glossary

33 May 28, 2026 Glossary of Abbreviations and Defined Terms AFS: Available-for-Sale ALCO: Asset and Liability Committee AML: Anti-Money Laundering AUM: Assets Under Management Basel III: Basel III Accord BVI: British Virgin Islands CAGR: Compound Annual Growth Rate CDI: Core Deposit Intangibles CET1: Common Equity Tier 1 Capital EPS: Earnings per Share FASB: Financial Accounting Standards Board FV: Fair Value GDP: Gross Domestic Product ICAAP: Internal Capital Adequacy Assessment Process IPO: Initial Public offering IRR: Internal Rate of Return Moody’s: Moody’s Investor Service NCO: Net Charge-Off NIM: Net Interest Margin NPL: Non-Performing Loans NYSE: New York Stock Exchange OECD: Organisation for Economic Co-operation and Development PCD: Purchased Credit Deteriorated ROAA: Return on Average Assets ROATCE: Return on Average Tangible Common Equity ROIC: Return on Invested Capital RWA: Risk-Weighted Assets SEC: Securities and Exchange Commission S&P: Standard & Poor’s TBVPS: Tangible Book Value per Share TBVPS Excl. AOCI: Tangible Book Value per Share excluding Accumulated Other Comprehensive Income (Loss) TCE: Tangible Common Equity TCE / TA: Tangible Common Equity / Tangible Assets TCI: Turks & Caicos Islands T&T: Trinidad & Tobago T2: Tier 2 Capital UN: United Nations VWAP: Volume Weighted Average Price

34 May 28, 2026 Appendix E: Risk Factor Summary

35 May 28, 2026 The following risk factors should be read in conjunction with the Forward-Looking Statements and Disclaimers set forth on page 2 of this presentation and the “Risk Factors” section of Butterfield’s most recent Form 20-F. • Closing Conditions; Regulatory and Shareholder Approval Risks. Completion of the proposed acquisition of CIBC Caribbean is subject to a number of conditions, including Butterfield shareholder approval of the share issuance and receipt of required regulatory and non-objection approvals from banking, securities, exchange-control, competition, stock exchange and other regulatory authorities. Such approvals may be delayed, not obtained or obtained subject to conditions, restrictions or requirements that could adversely affect Butterfield, CIBC Caribbean, the combined company or the expected benefits of the transaction. • Integration Risk. Butterfield’s ability to realize the anticipated strategic and financial benefits of the transaction - including projected cost savings, synergies, balance sheet and capital optimization initiatives, earnings accretion, and tangible book value per share accretion – depends on the successful integration of CIBC Caribbean’s businesses, operations, systems, controls, compliance programs, risk management framework, personnel and culture. Integration may prove more difficult, time-consuming or costly than expected, and assumptions underlying pro forma financials, purchase accounting, credit and fair value marks and synergy estimates may prove inaccurate. • Subordinated Debt Financing Risk. Butterfield expects to finance a portion of the cash consideration and related fees and expenses from the issuance and sale of subordinated notes or other subordinated debt securities. There is no assurance that such financing will be obtained on the expected terms, timing or at all, and changes to Butterfield’s share price, capital markets or other market conditions could adversely affect the cost or availability of such financing or the expected financial impact of the transaction. • Minority Shareholder and Compulsory Acquisition Risk. Butterfield intends to commence a mandatory take-over bid for the remaining CIBC Caribbean shares held by minority shareholders and plans to ultimately seek full ownership through compulsory acquisition, squeeze-out or similar processes. Any such minority shareholder offer, or related process could be delayed, not completed or completed on terms that differ from those currently expected, which could affect the anticipated post-closing ownership, capital and operating profile of the combined company. • Business Disruption and Retention Risk. Operating costs, customer loss and business disruption, including difficulties in maintaining relationships with employees, customers, clients, depositors, vendors, suppliers, regulators and other business partners, may be greater than expected, and management’s attention to ongoing operations may be disrupted by the pendency of the transaction. The announcement, pendency or completion of the transaction may also give rise to reputational risk, adverse stakeholder reactions, and the possibility of legal, regulatory or shareholder proceedings, inquiries or investigations. Risk Factor Summary

Filing Exhibits & Attachments

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Press Releases

• EX-99.1 EX-99.1 PRESS RELEASE BUTTERFIELD ANNOUNCES ACQUISITION OF CIBC CARIBBEAN 23.3 KB
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• EX-2.1 EX-2.1 SHARE PURCHASE AGREEMENT 403.6 KB
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