Upwork officer plans sale of 45,732 shares

Upwork, Inc. (UPWK) officer Anthony Ray Kappus has filed a Form 144 indicating an intent to sell 45,732 shares of Upwork common stock.

Rhea-AI Filing Summary

Upwork, Inc. (UPWK) officer Anthony Ray Kappus has filed a Form 144 indicating an intent to sell 45,732 shares of Upwork common stock. The planned sale is dated September 18, 2026 and is arranged through Morgan Stanley Smith Barney LLC Executive Financial Services.

The filing reports an aggregate market value of $386,476.56 for the 45,732 shares and references trading on NASDAQ. Over the prior three months, Kappus reported additional sales of 1,964 shares on August 18, 2026 for $16,548.07 and 558 shares on July 20, 2026 for $5,052.97.

Key Figures

Shares to be sold: 45,732 shares Aggregate market value of planned sale: $386,476.56 Shares sold on August 18, 2026: 1,964 shares +4 more

7 metrics

Shares to be sold 45,732 shares Common stock listed under Securities To Be Sold with date September 18, 2026

Aggregate market value of planned sale $386,476.56 Value associated with 45,732 shares of Upwork common stock in the securities information section

Shares sold on August 18, 2026 1,964 shares Securities Sold During The Past 3 Months by Anthony Kappus on August 18, 2026

Amount from August 18, 2026 sale $16,548.07 Common stock sale listed under Securities Sold During The Past 3 Months

Shares sold on July 20, 2026 558 shares Common stock sale by Anthony Kappus during the past 3 months

Amount from July 20, 2026 sale $5,052.97 Reported under Securities Sold During The Past 3 Months

Planned sale date September 18, 2026 Date associated with 45,732 shares of restricted common stock to be sold

Key Terms

Rule 144, Restricted Stock, Securities To Be Sold, Executive Financial Services

4 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Restricted Stock financial

"Common | 09/18/2026 | Restricted Stock | Issuer"

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

Securities To Be Sold financial

"144: Securities To Be Sold"

Executive Financial Services financial

"Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does the Form 144 filing disclose for UPWK and Anthony Kappus?

The filing discloses that officer Anthony Ray Kappus has notified of an intended sale of 45,732 shares of Upwork, Inc. common stock under Rule 144, with an indicated date of September 18, 2026 and an aggregate value of $386,476.56.

How many UPWK shares does Anthony Kappus plan to sell in this Form 144?

Anthony Ray Kappus plans to sell 45,732 shares of Upwork common stock. The filing lists these as restricted stock under the section “Securities To Be Sold,” with a proposed sale date of September 18, 2026.

What is the reported value of the UPWK shares in the planned Rule 144 sale?

The Form 144 reports an aggregate market value of $386,476.56 for the 45,732 shares of Upwork common stock to be sold, as shown in the securities information section accompanying the planned September 18, 2026 transaction.

Which broker is involved in Anthony Kappus’s planned UPWK share sale?

The filing lists Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, 8th Floor, New York, NY 10004, as the broker associated with the planned sale of 45,732 shares of Upwork common stock.

What UPWK stock sales has Anthony Kappus reported in the past 3 months?

Over the past three months, Anthony Ray Kappus reported selling 1,964 shares of Upwork common stock on August 18, 2026 for $16,548.07 and 558 shares on July 20, 2026 for $5,052.97 under the “Securities Sold During The Past 3 Months” section.

What type of UPWK securities are covered by this Form 144?

The Form 144 covers common stock of Upwork, Inc., described specifically as Restricted Stock in the “Securities To Be Sold” section, with the issuer identified as Upwork, Inc. and trading noted on NASDAQ.

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

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Available on EDGAR 09/18/2026 - 04:10 PM Accepted by SEC EDGAR 09/18/2026 - 04:10 PM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001860481
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	UPWORK INC.
SEC File Number	001-38678
Address of Issuer	530 Lytton Avenue, Suite 301 Palo Alto CALIFORNIA 94301
Phone	(650) 316-7500
Name of Person for Whose Account the Securities are To Be Sold	ANTHONY KAPPUS
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	45732	386476.56	124903365	09/18/2026	NASDAQ

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	09/18/2026	Restricted Stock	Issuer			45732	09/18/2026	Not Applicable

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
ANTHONY KAPPUS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	08/18/2026	1964	16548.07
ANTHONY KAPPUS 530 Lytton Avenue, Suite 301 Palo Alto CA 94301	Common	07/20/2026	558	5052.97

144: Remarks and Signature

Remarks
Date of Notice	09/18/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ Anthony Ray Kappus
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)