Upland Software (UPLD) CFO discloses RSU tax withholding share move

Rhea-AI Filing Summary

Upland Software, Inc. officer Micheal D. Hill, who serves as CFO, Treasurer and Secretary, reported an insider transaction involving company common stock. On 12/16/2025, 8,856 shares of common stock were disposed of at $1.485 per share with a transaction code "F," indicating shares were withheld by the issuer to satisfy tax withholding obligations tied to the vesting of restricted stock units, rather than sold in the open market.

Following this tax withholding event, Hill beneficially owned 331,222 shares of common stock directly. In addition, 160,042 shares were held indirectly through the MDH Trust, a trust for the benefit of his family for which he serves as trustee.

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
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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^*

Hill Michael Douglass

(Last) (First) (Middle)

900 S. CAPITAL OF TEXAS HWY

LAS CIMAS IV, SUITE 300

(Street)

AUSTIN TX 78746

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Upland Software, Inc. [ UPLD ]

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

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CFO, Treasurer & Secretary

3. Date of Earliest Transaction (Month/Day/Year)
12/16/2025

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

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

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

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	12/16/2025		F(1)		8,856	D	$1.485	331,222	D
Common Stock								160,042	I	Held by MDH Trust(2)

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

Explanation of Responses:

1. Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

2. Shares held by trust for the benefit of reporting person's family. Reporting person is the trustee of the trust.

Remarks:

	/s/ Micheal D. Hill	12/17/2025
	** 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.

FAQ

What insider transaction did Upland Software (UPLD) report for Micheal D. Hill?

Upland Software reported that officer Micheal D. Hill had 8,856 shares of common stock disposed of on 12/16/2025, recorded with transaction code "F" at a price of $1.485 per share.

Was the UPLD insider transaction an open market sale?

No. The filing states the 8,856 shares were withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units, and that this is not an open market sale of securities.

How many Upland Software shares does Micheal D. Hill own after the reported transaction?

After the transaction, Micheal D. Hill beneficially owned 331,222 shares of Upland Software common stock directly and 160,042 shares indirectly through the MDH Trust.

What is the MDH Trust mentioned in the Upland Software Form 4?

The MDH Trust holds 160,042 Upland Software shares for the benefit of Micheal D. Hill's family, and he is identified as the trustee of the trust.

What is Micheal D. Hill’s role at Upland Software (UPLD)?

Micheal D. Hill is an officer of Upland Software, serving as CFO, Treasurer & Secretary, as indicated in the filing.

What does transaction code "F" mean in the Upland Software insider filing?

The explanation states that the code "F" corresponds to shares withheld by the issuer to satisfy tax withholding obligations related to vesting restricted stock units.