S-8

As filed with the Securities and Exchange Commission on October 31, 2023

SEC Registration No. 333-

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM S-8

REGISTRATION STATEMENT

UNDER

THE SECURITIES ACT OF 1933

TOMPKINS FINANCIAL CORPORATION

(Exact name of registrant as specified in its charter)

NEW YORK

(State or other jurisdiction of incorporation or organization)

16-1482357

(I.R.S. Employer Identification No.)

118 E. Seneca Street, P.O. Box 460

Ithaca, New York 14851

(Address of Principal Executive Offices) (Zip Code)

2019 EQUITY INCENTIVE PLAN

(Full title of the plan)

Matthew D. Tomazin	with a copy to:
Executive Vice President, Chief Financial Officer	Alyssa H. Fontaine
Tompkins Financial Corporation	Executive Vice President, General Counsel, and
P.O. Box 460	Chief Risk Officer
Ithaca, New York 14851	Tompkins Financial Corporation
	P.O. Box 460
	Ithaca, New York 14851

 (Name and Address of Agent For Service)

(607) 274-7685

(Telephone number, including area code, of agent for service)

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “non-accelerated filer,” “smaller reporting company,” and emerging growth company” in Rule 12b-2 of the Exchange Act. (Check one):

Large accelerated filer	☒	Accelerated filer	☐
Non-accelerated filer	☐	Smaller reporting company	☐
		Emerging Growth Company	☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 7(a)(2)(B) of the Securities Act. ☐

EXPLANATORY NOTE

This Registration Statement on Form S-8 (this “Registration Statement”) is being filed by Tompkins Financial Corporation (the “Company,” “Registrant,” “we,” “us” or “our”) to register an additional 1,000,000 shares of common stock for issuance under the Tompkins Financial Corporation 2019 Equity Incentive Plan, as amended (the “Plan”). The Plan was amended on April 27, 2023 to increase the number of shares of common stock authorized for issuance pursuant to the Plan by 1,000,000 shares. Pursuant to General Instruction E of Form S-8, this Registration Statement incorporates by reference the contents of the Registrant’s previous Registration Statement on Form S-8 (No. 333-231413) filed with the Securities and Exchange Commission (the “Commission”) on May 13, 2019, except as modified herein.

PART II

INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

Item 3. Incorporation of Documents by Reference.

The following documents that the Registrant has filed with the Commission under the Securities Exchange Act of 1934 (the “Exchange Act”) are incorporated by reference into this Registration Statement:

(a) the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022;

(b) the Company’s Quarterly Reports on Form 10-Q for the fiscal quarters ended March 31, 2023 and June 30, 2023;

(c) the Company’s Current Reports on Form 8-K to the extent filed and not furnished with the Commission on January 27, 2023, April 28, 2023, May 3, 2023, May 9, 2023, May 11, 2023, July 12, 2023, July 21, 2023, September 18, 2023, September 29, 2023, and October 27, 2023;

(d) The description of the Common Stock of the Registrant included as Exhibit 4.2 to the Registrant’s Annual Report on Form 10-K for the fiscal year ended December 31, 2019 and filed with the Commission on March 2, 2020.

In addition, all reports and other documents subsequently filed (but not furnished) by the Registrant pursuant to Sections 13(a), 14 and 15(d) of the Exchange Act, prior to the filing of a post-effective amendment that indicates that all securities offered have been sold or that deregisters all securities then remaining unsold, shall be deemed to be incorporated by reference in this Registration Statement and to be a part hereof from the date of filing of such documents with the Commission. Any statement contained in a document incorporated or deemed to be incorporated by reference in this Registration Statement shall be deemed to be modified or superseded for purposes of this Registration Statement to the extent that a statement contained in this Registration Statement, or in any other subsequently filed document that also is or is deemed to be incorporated by reference in this Registration Statement, modifies or supersedes such prior statement. Any statement contained in this Registration Statement shall be deemed to be modified or superseded to the extent that a statement contained in a subsequently filed document that is or is deemed to be incorporated by reference in this Registration Statement modifies or supersedes such prior statement. Any statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute a part of this Registration Statement.

No document or information deemed to be furnished and not filed in accordance with rules of the Commission shall be deemed to be incorporated herein by reference unless such document or information expressly provides to the contrary.

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Item 8. Exhibits.

The following exhibits are filed with this Registration Statement:

4.1	Amended and Restated Certificate of Incorporation of the Company, incorporated herein by reference to Exhibit 3(i) to the Company’s Form 10-Q, filed with the Commission on August 11, 2008.
4.2	Second Amended and Restated Bylaws of the Company, incorporated herein by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K, filed with the Commission on January 31, 2011.
4.3	Form of Specimen Common Stock Certificate of the Company, incorporated herein by reference to Exhibit 4 to the Company’s Registration Statement on Form 8-A (No. 0-27514), filed with the Commission on December 29, 1995.
4.4	Description of Securities Registered Under Section 12 of the Exchange Act, incorporated herein by reference to Exhibit 4.2 to the Company's Annual Report on Form 10-K, filed with the Commission on March 2, 2020.
4.5	Tompkins Financial Corporation 2019 Equity Incentive Plan, incorporated herein by reference to Appendix A of the Company’s DEF 14A filed with the commission on March 29, 2019.
4.6	Amendment No. 1 to the Tompkins Financial Corporation 2019 Equity Incentive Plan, incorporated herein by reference to Exhibit 10.1 to the Company’s Quarterly Report on Form 10-Q filed with the Commission on August 9, 2023.
5*	Opinion of Holland & Knight LLP
23.1*	Consent of KPMG LLP, Independent Registered Public Accounting Firm
23.2*	Consent of Holland & Knight LLP (included in Exhibit 5)
24*	Power of Attorney (included at pages II-3 and II-4)
107*	Filing Fee Table

*filed herewith

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SIGNATURES

Pursuant to the requirements of the Securities Act of 1933, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements for filing on Form S-8 and has duly caused this Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of Ithaca, state of New York, on this 31^st day of October, 2023.

TOMPKINS FINANCIAL CORPORATION
By:	/s/ Stephen S. Romaine
	Stephen S. Romaine
	President and Chief Executive Officer

POWER OF ATTORNEY

KNOW ALL PERSONS BY THESE PRESENTS, that each person whose signature appears below constitutes and appoints, jointly and severally, Stephen S. Romaine and Matthew D. Tomazin and each of them, as their true and lawful attorneys-in-fact and agents, each with full power of substitution, for them, and in their name, place and stead, and in any and all capacities, to sign any and all amendments (including post-effective amendments) to this Registration Statement on Form S-8, and to file the same, with all exhibits thereto and other documents in connection therewith, with the Securities and Exchange Commission, granting unto said attorneys-in-fact and agents, and each of them, full power and authority to do and perform each and every act and thing requisite or necessary to be done as fully to all intents and purposes as they might or could do in person, hereby ratifying and confirming all that said attorneys-in-fact and agents, or any of them, or their substitutes, may lawfully do or cause to be done by virtue hereof.

Pursuant to the requirements of the Securities Exchange Act of 1933, this Registration Statement and Power of Attorney have been signed below by the following persons in the capacities and on the dates indicated:

Name	Capacity	Date
/s/ Stephen S. Romaine	President and Chief Executive Officer, Director (Principal Executive Officer)	October 31, 2023
Stephen S. Romaine
/s/ Matthew D. Tomazin	Executive Vice President, Chief Financial Officer (Principal Financial Officer)	October 31, 2023
Matthew D. Tomazin
/s/ David Kershaw	Senior Vice President, Chief Accounting Officer (Principal Accounting Officer)	October 31, 2023
David Kershaw
/s/ Thomas R. Rochon	Chair of the Board	October 31, 2023
Thomas R. Rochon
/s/ James W. Fulmer	Vice Chair, Director	October 31, 2023
James W. Fulmer

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/s/ John E. Alexander	Director	October 31, 2023
John E. Alexander
/s/ Paul J. Battaglia	Director	October 31, 2023
Paul J. Battaglia
/s/ Nancy E. Catarisano	Director	October 31, 2023
Nancy E. Catarisano
/s/ Daniel J. Fessenden	Director	October 31, 2023
Daniel J. Fessenden
/s/ Patricia A.  Johnson	Director	October 31, 2023
Patricia A. Johnson
/s/ Angela B. Lee	Director	October 31, 2023
Angela B. Lee
/s/ John D. McClurg	Director	October 31, 2023
John D. McClurg
/s/ Ita M. Rahilly	Director	October 31, 2023
Ita. M. Rahilly
/s/ Michael H. Spain	Director	October 31, 2023
Michael H. Spain
/s/ Jennifer R. Tegan	Director	October 31, 2023
Jennifer R. Tegan
/s/ Alfred J. Weber	Director	October 31, 2023
Alfred J. Weber

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EX-5.1

Tompkins Financial Corporation S-8

Exhibit 5.1

October 31, 2023

Board of Directors

Tompkins Financial Corporation

P.O. Box 460

Ithaca, New York 14851

Re: Registration Statement on Form S-8 of Tompkins Financial Corporation

Dear Ladies and Gentlemen:

On or about the date hereof, Tompkins Financial Corporation, a New York corporation (the “Company”), transmitted for filing with the Securities and Exchange Commission (the “Commission”) a Registration Statement on Form S-8 pursuant to the Securities Act of 1933, as amended (the “Securities Act”). The Registration Statement relates to 1,000,000 shares (the “Shares”) of the Company’s common stock, $0.10 par value per share (“Common Stock”), issuable under the Company’s Tompkins Financial Corporation 2019 Equity Incentive Plan, as amended by Amendment No. 1 to the Plan (the “Plan”). We have acted as counsel to the Company in connection with the preparation and filing of the Registration Statement.

In connection therewith, we have examined and relied upon the original or a copy, certified or otherwise identified to our satisfaction, of: (i) the Company’s Amended and Restated Certificate of Incorporation, as amended and restated to date (the “Certificate”), and Second Amended and Restated Bylaws, as amended to the date hereof; (ii) records of corporate proceedings (the “Corporate Proceedings”) of the Company related to the Plan; (iii) the Registration Statement and exhibits thereto; and (iv) such other documents, instruments and records as we have deemed necessary for the expression of the opinions contained herein.

We have assumed the genuineness of all signatures, the legal capacity of all natural persons, the authenticity of the documents submitted to us as originals, the conformity with the originals of all documents submitted to us as certified, facsimile or photostatic copies and the authenticity of the originals of all documents submitted to us as copies.

Based upon the foregoing examination, and subject to the assumptions, qualifications and limitations stated herein, and assuming that the consideration, if any, required to be paid in connection with the issuance and sale of Shares under the Plan is actually received by the Company as provided in the Plan, we are of the opinion that the Shares issued under the Plan will be duly authorized, validly issued, fully paid and nonassessable.

The opinion rendered herein is limited to the New York Business Corporation Law, as amended. We express no opinion herein as to any other statutes, rules or regulations.

This opinion is rendered solely in connection with the filing of the Registration Statement, is limited to the matters stated herein, and no opinions may be implied or inferred beyond the matters expressly stated herein. This opinion may not be relied upon for any other purpose without our prior written consent in each instance. Further, no portion of this letter may be quoted, circulated or referred to in any other document for any other purpose without our prior written consent.

We hereby consent to the filing of this opinion as Exhibit 5.1 to the Registration Statement.  In giving such consent, we do not thereby admit that we are in the category of persons whose consent is required under Section 7 of the Securities Act or the rules and regulations of the Commission promulgated thereunder.

Sincerely yours,

/s/ Holland & Knight LLP

HOLLAND & KNIGHT LLP

2

EX-23.1

Tompkins Financial Corporation S-8

Exhibit 23.1

Consent of Independent Registered Public Accounting Firm

We consent to the use of our reports dated March 1, 2023, with respect to the consolidated financial statements of Tompkins Financial Corporation, and the effectiveness of internal control over financial reporting, incorporated herein by reference.

/s/ KPMG LLP

Rochester, New York

October 31, 2023

EX-FILING FEES

Tompkins Financial Corporation S-8

Exhibit 107

Calculation of Filing Fee Tables

Form S-8
(Form Type)

Tompkins Financial Corporation
(Exact Name of Registrant as Specified in its Charter)

Table 1 -- Newly Registered Securities

Security Type	Security Class Title	Fee Calculation Rule	Amount Registered(1)	Proposed Maximum Offering Price Per Unit(3)	Maximum Aggregate Offering Price(3)	Fee Rate	Amount of Registration Fee
Equity	Common Stock, par value $0.10	457(h)(1) and 457(c)	1,000,000(2)	$49.57	$49,570,000.00	0.00014760	$7,316.53
Total Offering Amounts							$7,316.53
Total Fee Offsets(4)							--
Net Fee Due							$7,316.53

(1) Pursuant to Rule 416(a), the Registration Statement also includes an indeterminate number of additional shares that may become issuable pursuant to antidilution provisions of the 2019 Equity Incentive Plan.

(2) Represents 1,000,000 additional shares of common stock reserved for issuance under the Registrant’s 2019 Equity Incentive Plan.

(3) In accordance with Rules 457(h) and 457(c), calculated on the basis of the average of the high and low prices of the Common Stock on the NYSE American on October 27, 2023.

(4) The Registrant does not have any fee offsets.