OBT Completes $25M Private Debt Placement; Piper Sandler as Broker

Rhea-AI Filing Summary

Orange County Bancorp, Inc. filed a Form D announcing a completed exempt offering under Rule 506(b) for debt securities totaling $25,000,000. The issuer is a Delaware corporation with principal offices in Middletown, New York. The offering sold the full amount with 21 investors and a minimum outside investment of $100,000. Piper Sandler & Co. acted as (associated) broker-dealer. Reported sales commissions were $375,000. The company stated $0 of proceeds were used to pay named officers, directors or promoters. The notice was signed by EVP & CFO Michael Lesler.

Positive

• Full subscription: The offering amount of $25,000,000 was fully sold, with Total Remaining to be Sold $0.
• No insider payments: The filing reports $0 of proceeds used to pay named officers, directors, or promoters.
• Registered broker-dealer: Piper Sandler & Co. is identified as the (associated) broker-dealer, providing an organized placement channel.

Negative

• Distribution cost disclosed: Sales commissions of $375,000 were paid, increasing net proceeds to the issuer.
• High minimum investment: The $100,000 minimum may limit participation to accredited or institutional investors, concentrating the investor base.

Insights

Securities Analyst

TL;DR: Completed $25M Rule 506(b) debt offering sold to 21 investors; Piper Sandler involved; commissions disclosed.

The filing documents a fully subscribed private debt offering under Rule 506(b) totaling $25,000,000. The presence of an established broker-dealer and disclosure of sales compensation provides transparency on distribution costs. The minimum $100,000 investor threshold indicates this was aimed at accredited or institutional investors. No proceeds were reported as paid to insiders, which reduces immediate governance or related-party concerns. Overall, the filing is a routine private placement disclosure.

Financial Analyst

TL;DR: The completed offering raises $25M in debt capital with $375k in commissions; limited investor count.

The capital raise increases the issuer's debt financing by $25,000,000 as documented. Sales commissions of $375,000 are disclosed, representing an explicit cost of issuance. The offering lists 21 investors and a $100,000 minimum investment, suggesting a concentrated, higher‑ticket investor base. The filing does not state how proceeds will be deployed beyond excluding payments to listed insiders. From a financial perspective, this is a standard Form D reporting of a private debt placement.

The Securities and Exchange Commission has not necessarily reviewed the information in this filing and has not determined if it is accurate and complete.
The reader should not assume that the information is accurate and complete.

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

Notice of Exempt Offering of Securities

OMB APPROVAL

OMB Number:			3235-0076
Estimated average burden
hours per response:			4.00

1. Issuer's Identity

CIK (Filer ID Number)

Previous Names

X None

Entity Type

0001754226

X	Corporation
	Limited Partnership
	Limited Liability Company
	General Partnership
	Business Trust
	Other (Specify)

Name of Issuer

Orange County Bancorp, Inc. /DE/

Jurisdiction of Incorporation/Organization

DELAWARE

Year of Incorporation/Organization

X	Over Five Years Ago
	Within Last Five Years (Specify Year)
	Yet to Be Formed

2. Principal Place of Business and Contact Information

Name of Issuer
Orange County Bancorp, Inc. /DE/
Street Address 1		Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode	Phone Number of Issuer
Middletown	NEW YORK	10940	8453415000

3. Related Persons

Last Name	First Name	Middle Name
Gilfeather	Michael	J.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: X Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Holcombe	Gregory	F.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Keane	Kevin	J.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Kennedy	Marianna	R.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Morrison	William	D.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Rouis	Jonathan	F.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Rowley	Richard	B.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Schiller	Jonathan
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Tirado	Olga	Luz
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: Executive Officer X Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Lesler	Michael
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: X Executive Officer Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Ruhl	Joseph	A.
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: X Executive Officer Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Sousa	Gregory
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: X Executive Officer Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Dineen	David
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: X Executive Officer Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Coulter	Michael
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: X Executive Officer Director Promoter

Clarification of Response (if Necessary):

Last Name	First Name	Middle Name
Jones	Elizabeth
Street Address 1	Street Address 2
212 Dolson Avenue
City	State/Province/Country	ZIP/PostalCode
Middletown	NEW YORK	10940

Relationship: X Executive Officer Director Promoter

Clarification of Response (if Necessary):

4. Industry Group

Agriculture

Banking & Financial Services

X

Commercial Banking

Insurance

Investing

Investment Banking

Pooled Investment Fund

Is the issuer registered as
an investment company under
the Investment Company
Act of 1940?

Yes No

Other Banking & Financial Services

Business Services

Energy

Coal Mining

Electric Utilities

Energy Conservation

Environmental Services

Oil & Gas

Other Energy

	Health Care
	Biotechnology
	Health Insurance
	Hospitals & Physicians
	Pharmaceuticals
	Other Health Care
	Manufacturing
	Real Estate
	Commercial
	Construction
	REITS & Finance
	Residential
	Other Real Estate

Retailing

Restaurants

Technology

Computers

Telecommunications

Other Technology

Travel

Airlines & Airports

Lodging & Conventions

Tourism & Travel Services

Other Travel

Other

5. Issuer Size

Revenue Range		OR	Aggregate Net Asset Value Range
	No Revenues			No Aggregate Net Asset Value
	$1 - $1,000,000			$1 - $5,000,000
	$1,000,001 - $5,000,000			$5,000,001 - $25,000,000
	$5,000,001 - $25,000,000			$25,000,001 - $50,000,000
	$25,000,001 - $100,000,000			$50,000,001 - $100,000,000
	Over $100,000,000			Over $100,000,000
X	Decline to Disclose			Decline to Disclose
	Not Applicable			Not Applicable

6. Federal Exemption(s) and Exclusion(s) Claimed (select all that apply)

		Rule 504(b)(1) (not (i), (ii) or (iii))
		Rule 504 (b)(1)(i)
		Rule 504 (b)(1)(ii)
		Rule 504 (b)(1)(iii)
	X	Rule 506(b)
		Rule 506(c)
		Securities Act Section 4(a)(5)

Investment Company Act Section 3(c)

Section 3(c)(1) Section 3(c)(9)

Section 3(c)(2) Section 3(c)(10)

Section 3(c)(3) Section 3(c)(11)

Section 3(c)(4) Section 3(c)(12)

Section 3(c)(5) Section 3(c)(13)

Section 3(c)(6) Section 3(c)(14)

Section 3(c)(7)

7. Type of Filing

X	New Notice			Date of First Sale	2025-09-25				First Sale Yet to Occur
	Amendment

8. Duration of Offering

Does the Issuer intend this offering to last more than one year? Yes X No

9. Type(s) of Securities Offered (select all that apply)

	Equity		Pooled Investment Fund Interests
X	Debt		Tenant-in-Common Securities
	Option, Warrant or Other Right to Acquire Another Security		Mineral Property Securities
	Security to be Acquired Upon Exercise of Option, Warrant or Other Right to Acquire Security		Other (describe)

10. Business Combination Transaction

Is this offering being made in connection with a business combination transaction, such as a merger, acquisition or exchange offer? Yes X No

Clarification of Response (if Necessary):

11. Minimum Investment

Minimum investment accepted from any outside investor $100,000 USD

12. Sales Compensation

Recipient	Recipient CRD Number None
Piper Sandler & Co.	665
(Associated) Broker or Dealer X None	(Associated) Broker or Dealer CRD Number X None
None	None
Street Address 1	Street Address 2
1251 Avenue of the Americas	6th Floor
City	State/Province/Country	ZIP/Postal Code
New York	NEW YORK	10020
State(s) of Solicitation (select all that apply) Check "All States" or check individual States X All States	Foreign/non-US

13. Offering and Sales Amounts

Total Offering Amount	$25,000,000	USD	or Indefinite
Total Amount Sold	$25,000,000	USD
Total Remaining to be Sold	$0	USD	or Indefinite

Clarification of Response (if Necessary):

14. Investors

Select if securities in the offering have been or may be sold to persons who do not qualify as accredited investors, and enter the number of such non-accredited investors who already have invested in the offering.

Regardless of whether securities in the offering have been or may be sold to persons who do not qualify as accredited investors, enter the total number of investors who already have invested in the offering:

21

15. Sales Commissions & Finder's Fees Expenses

Provide separately the amounts of sales commissions and finders fees expenses, if any. If the amount of an expenditure is not known, provide an estimate and check the box next to the amount.

Sales Commissions	$375,000	USD	Estimate
Finders' Fees	$0	USD	Estimate

Clarification of Response (if Necessary):

16. Use of Proceeds

Provide the amount of the gross proceeds of the offering that has been or is proposed to be used for payments to any of the persons required to be named as executive officers, directors or promoters in response to Item 3 above. If the amount is unknown, provide an estimate and check the box next to the amount.

$0

USD

Estimate

Clarification of Response (if Necessary):

Signature and Submission

Please verify the information you have entered and review the Terms of Submission below before signing and clicking SUBMIT below to file this notice.

Terms of Submission

In submitting this notice, each issuer named above is:

• Notifying the SEC and/or each State in which this notice is filed of the offering of securities described and undertaking to furnish them, upon written request, in the accordance with applicable law, the information furnished to offerees.*

• Irrevocably appointing each of the Secretary of the SEC and, the Securities Administrator or other legally designated officer of the State in which the issuer maintains its principal place of business and any State in which this notice is filed, as its agents for service of process, and agreeing that these persons may accept service on its behalf, of any notice, process or pleading, and further agreeing that such service may be made by registered or certified mail, in any Federal or state action, administrative proceeding, or arbitration brought against the issuer in any place subject to the jurisdiction of the United States, if the action, proceeding or arbitration (a) arises out of any activity in connection with the offering of securities that is the subject of this notice, and (b) is founded, directly or indirectly, upon the provisions of: (i) the Securities Act of 1933, the Securities Exchange Act of 1934, the Trust Indenture Act of 1939, the Investment Company Act of 1940, or the Investment Advisers Act of 1940, or any rule or regulation under any of these statutes, or (ii) the laws of the State in which the issuer maintains its principal place of business or any State in which this notice is filed.

• Certifying that, if the issuer is claiming a Regulation D exemption for the offering, the issuer is not disqualified from relying on Rule 504 or Rule 506 for one of the reasons stated in Rule 504(b)(3) or Rule 506(d).

Each Issuer identified above has read this notice, knows the contents to be true, and has duly caused this notice to be signed on its behalf by the undersigned duly authorized person.

For signature, type in the signer's name or other letters or characters adopted or authorized as the signer's signature.

Issuer	Signature	Name of Signer	Title	Date
Orange County Bancorp, Inc. /DE/	/s/ Michael Lesler	Michael Lesler	EVP and CFO	2025-09-30

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.

* This undertaking does not affect any limits Section 102(a) of the National Securities Markets Improvement Act of 1996 ("NSMIA") [Pub. L. No. 104-290, 110 Stat. 3416 (Oct. 11, 1996)] imposes on the ability of States to require information. As a result, if the securities that are the subject of this Form D are "covered securities" for purposes of NSMIA, whether in all instances or due to the nature of the offering that is the subject of this Form D, States cannot routinely require offering materials under this undertaking or otherwise and can require offering materials only to the extent NSMIA permits them to do so under NSMIA's preservation of their anti-fraud authority.

FAQ

What was the size and type of the offering reported by Orange County Bancorp (OBT)?

The Form D reports a $25,000,000 offering of debt securities under Rule 506(b).

How many investors participated and what was the minimum investment for OBT's offering?

The filing shows 21 investors participated and the minimum outside investment accepted was $100,000.

Were any proceeds used to pay officers, directors, or promoters?

No. The Form D reports $0 of the gross proceeds were used for payments to named officers, directors, or promoters.

Who acted as the broker-dealer and what were the sales commissions?

Piper Sandler & Co. acted as the (associated) broker-dealer and reported sales commissions of $375,000.

Is the offering still open or completed?

The filing indicates the total offering amount was $25,000,000, Total Amount Sold $25,000,000, and Total Remaining to be Sold $0, indicating the offering has been fully sold.