Community Financial (NYSE: CBU) CAO exercises stock options, withholds shares for taxes

Rhea-AI Filing Summary

Community Financial System, Inc. senior vice president and chief accounting officer Deresa Fischer reported routine equity compensation activity. She exercised stock options covering 1,623 shares of common stock at exercise prices of $44.27 and $51.64 per share, and 1,326 shares were disposed of to cover tax obligations at $64.77 per share. Following these transactions, she directly holds 5,477.604 common shares, with additional indirect holdings through a spouse and a 401(k) plan.

Insights

Equity compensation and insider-transactions analyst

Routine option exercises with tax withholding, no open-market trades.

The filing shows Deresa Fischer, SVP and chief accounting officer, exercising stock options for 1,623 common shares at exercise prices of $44.27 and $51.64. This converts derivative awards into owned stock, a standard feature of equity compensation.

To satisfy tax obligations, 1,326 shares were disposed of at $64.77 per share, classified as a tax-withholding transaction, not an open-market sale. After these entries, she holds 5,477.604 common shares directly plus smaller indirect positions via a spouse and the company’s 401(k) plan.

Because there are no open-market purchases or sales and the activity aligns with vesting schedules noted in the footnotes, this looks like routine compensation management rather than a directional bet on the stock, so the informational impact for investors is limited.

Insider Trade Summary

1,623 shares exercised/converted

Mixed 7 txns

Insider Durkee Deresa Fischer

Role SVP, Chief Accounting Officer

Type	Security	Shares	Price	Value
Exercise	Stock Option	427	$0.00	--
Exercise	Stock Option	1,196	$0.00	--
Exercise	Common Stock	427	$51.64	$22K
Exercise	Common Stock	1,196	$44.27	$53K
Tax Withholding	Common Stock	1,326	$64.77	$86K
holding	Common Stock	--	--	--
holding	Common Stock	--	--	--

Holdings After Transaction: Stock Option — 0 shares (Direct, null); Common Stock — 5,607.604 shares (Direct, null); Common Stock — 710.252 shares (Indirect, By 401(k))

Footnotes (1)

1. The number of shares reported herein acquired pursuant to Community Financial System, Inc.'s 401(k) Plan and are based on a current plan statement. The option vested ratably on March 17, 2021, 2022, 2023, 2024, and 2025. The option vests ratably on March 19, 2025, 2026, 2027, 2028, and 2029.

Key Figures

Option shares exercised: 1,623 shares Tax-withheld shares: 1,326 shares Exercise price 1: $44.27/share +5 more

8 metrics

Option shares exercised 1,623 shares Common stock acquired via option exercises on 2026-06-10

Tax-withheld shares 1,326 shares Shares delivered to cover tax liability at $64.77/share

Exercise price 1 $44.27/share Exercise price for 1,196 option shares

Exercise price 2 $51.64/share Exercise price for 427 option shares

Post-transaction direct holdings 5,477.604 shares Directly held common stock after transactions

Spouse indirect holdings 218 shares Common stock held indirectly via spouse

401(k) indirect holdings 710.2515 shares Common stock held through Community Financial 401(k) Plan

Remaining option grant 1,794 options Stock options with $44.27 exercise price expiring 2034-03-19

Key Terms

401(k) Plan, Stock Option, tax-withholding disposition, derivative security, +1 more

5 terms

401(k) Plan financial

"acquired pursuant to Community Financial System, Inc.'s 401(k) Plan"

A 401(k) plan is a workplace retirement account that lets employees set aside part of their pay into a tax-advantaged savings pot, often with employers adding matching contributions — like a workplace piggy bank for future income. It matters to investors because the amount people save and how employers fund these plans influence consumer spending, corporate payroll costs and the flow of money into financial markets, which can affect stock prices and company valuations.

Stock Option financial

"security_title": "Stock Option""

A stock option is a contract that gives you the right to buy or sell a company's stock at a specific price within a certain time frame. People use them to potentially make money if the stock's price moves favorably or to protect against losses. It's like holding a coupon that can be used to buy or sell stock at a set price later on.

tax-withholding disposition financial

"transaction_action": "tax-withholding disposition""

A tax-withholding disposition is an event or transaction—such as selling or transferring securities, exercising options, or receiving compensation—that triggers a requirement to hold back part of the payment and remit it to tax authorities. It matters to investors because it reduces the cash they receive immediately and can change the timing and amount of taxable income, like a cashier taking a portion of your sale proceeds to pay taxes before you get the rest.

derivative security financial

"transaction_code_description": "Exercise or conversion of derivative security""

A derivative security is a financial contract whose value comes from the price or performance of something else, such as a stock, bond, commodity, or market index. For investors it acts like an insurance policy or a wager: it can be used to protect against losses, lock in prices, or amplify gains and losses, so it can change a portfolio’s risk and potential return without owning the underlying asset directly.

vested ratably financial

"The option vested ratably on March 17, 2021, 2022, 2023, 2024, and 2025."

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Form 4 Insider Transactions: What Each Field Means →

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Durkee Deresa Fischer

(Last) (First) (Middle)

C/O COMMUNITY FINANCIAL SYSTEM, INC.

333 BUTTERNUT DRIVE

(Street)

SYRACUSE NEW YORK 13214

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
COMMUNITY FINANCIAL SYSTEM, INC. [ CBU ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	SVP, Chief Accounting Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/10/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	06/10/2026		M		427	A	$51.64	5,607.604	D
Common Stock	06/10/2026		M		1,196	A	$44.27	6,803.604	D
Common Stock	06/10/2026		F		1,326	D	$64.77	5,477.604	D
Common Stock								710.2515	I	By 401(k)(1)
Common Stock								218	I	By spouse

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Stock Option	$51.64	06/10/2026		M			427	(2)	03/17/2030	Common Stock	427	$0	0	D
Stock Option	$44.27	06/10/2026		M			1,196	(3)	03/19/2034	Common Stock	1,196	$0	1,794	D

Explanation of Responses:

1. The number of shares reported herein acquired pursuant to Community Financial System, Inc.'s 401(k) Plan and are based on a current plan statement.

2. The option vested ratably on March 17, 2021, 2022, 2023, 2024, and 2025.

3. The option vests ratably on March 19, 2025, 2026, 2027, 2028, and 2029.

	/s/ Danielle M. Cima, pursuant to a Confirming Statement executed by Deresa F. Durkee	06/11/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

FAQ

What insider transactions did CBU executive Deresa Fischer report on this Form 4?

Deresa Fischer reported exercising stock options for 1,623 shares of Community Financial System common stock and a related tax-withholding disposition of 1,326 shares. These entries reflect routine equity compensation activity rather than open-market buying or selling by the executive.

Did the CBU chief accounting officer buy or sell shares on the open market?

The filing does not show any open-market purchases or sales. It records option exercises and a tax-withholding disposition, where shares are delivered to cover taxes on vested equity awards, a common non-discretionary compensation mechanism for executives.

How many CBU shares does Deresa Fischer hold after the reported transactions?

After the transactions, Deresa Fischer holds 5,477.604 Community Financial System common shares directly. She also has indirect holdings of 218 shares through her spouse and 710.2515 shares through the company’s 401(k) plan, based on a current plan statement.

What were the exercise prices of the CBU stock options exercised by Deresa Fischer?

She exercised stock options for 1,196 shares at an exercise price of $44.27 per share and 427 shares at $51.64 per share. These options were granted previously and vested ratably over several years according to the vesting schedules in the footnotes.

Why were 1,326 CBU shares classified as a tax-withholding disposition?

The 1,326 shares classified with code F were delivered to cover tax liabilities associated with equity awards. This mechanism allows taxes to be paid using shares instead of cash and is treated differently from open-market sales, carrying limited signaling value about the insider’s view.

What do the Form 4 footnotes say about CBU 401(k) holdings and option vesting?

One footnote states the 401(k) shares are based on a current plan statement. Other footnotes explain that specific options vested ratably over multiple years ending in 2025 and beginning in 2025, clarifying these exercises follow established vesting schedules.