Upwork officer Kappus proposes $4.71K share sale

The September 18, 2026 prior-sale entry pairs 45,732 shares with a reported amount of $386,476.56.

Rhea-AI Filing Summary

Upwork, Inc. officer Anthony Kappus reported a proposed sale of 559 shares of common stock, with an aggregate market value of $4,712.03 and an approximate sale date of October 19, 2026. Morgan Stanley Smith Barney LLC is listed as the broker and NASDAQ as the exchange. The shares are identified as restricted stock acquired from the issuer on October 18, 2026. Earlier sales listed were 45,732 shares on September 18, 1,964 shares on August 18, and 558 shares on July 20, 2026. Anthony Ray Kappus is named as signatory.

Key Figures

Shares proposed for sale: 559 shares Aggregate market value of proposed sale: $4,712.03 Shares sold: 45,732 shares +5 more

8 metrics

Shares proposed for sale 559 shares Common stock; approximate sale date October 19, 2026

Aggregate market value of proposed sale $4,712.03 559 shares proposed for sale

Shares sold 45,732 shares September 18, 2026 prior sale

Reported amount $386,476.56 September 18, 2026 prior sale

Shares sold 1,964 shares August 18, 2026 prior sale

Reported amount $16,548.07 August 18, 2026 prior sale

Shares sold 558 shares July 20, 2026 prior sale

Reported amount $5,052.97 July 20, 2026 prior sale

Key Terms

Rule 144, Restricted Stock, person

3 terms

Rule 144 regulatory

"sales are required by paragraph (e) of Rule 144 to be aggregated"

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

"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.

person regulatory

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

FAQ

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

How many UPWK shares does Anthony Kappus propose to sell?

Upwork officer Anthony Kappus reported a proposed sale of 559 common shares, with an aggregate market value of $4,712.03 and an approximate sale date of October 19, 2026. Morgan Stanley Smith Barney LLC is listed as the broker.

What prior UPWK share sales did Anthony Kappus report?

The listed sales were 45,732 shares with a reported amount of $386,476.56 on September 18, 2026; 1,964 shares with $16,548.07 on August 18, 2026; and 558 shares with $5,052.97 on July 20, 2026.

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

See more from StockTitan in Google Search and AI answers. Adds StockTitan as a preferred source · opens Google

Add on Google Not now

Available on EDGAR 10/19/2026 - 04:41 PM EDT Accepted by SEC EDGAR 10/19/2026 - 04:41 PM EDT 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	559	4712.03	124903365	10/19/2026	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	10/18/2026	Restricted Stock	Issuer			559	10/18/2026	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	09/18/2026	45732	386476.56
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	10/19/2026
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)