Oscar Health officer plans sale of 25,000 shares

An Oscar Health officer filed a Rule 144 notice to sell up to 25,000 Class A shares valued at $806,000 through Merrill Lynch.

Rhea-AI Filing Summary

Oscar Health, Inc. (OSCR) is the issuer for a planned sale of its Class A Common Stock by officer Vanessa Wittman under a Rule 144 notice. The notice covers up to 25,000 shares, with an aggregate market value of $806,000, to be sold through Merrill Lynch on the NYSE on or about September 18, 2026.

The filing reports that 273,469 shares of this class were outstanding in the relevant Form 144 table. The shares to be sold stem from vesting of restricted stock unit awards granted as part of Oscar Health’s equity compensation plan, including tranches of 8,333 shares on September 1, 2021 and 4,167 or 4,166 shares vesting on multiple dates in 2021–2022.

Key Figures

Shares to be sold: 25,000 shares Aggregate market value: $806,000 Shares outstanding (class referenced): 273,469 shares +3 more

6 metrics

Shares to be sold 25,000 shares Class A Common Stock covered by the Rule 144 notice

Aggregate market value $806,000 Reported value of the 25,000 shares to be sold

Shares outstanding (class referenced) 273,469 shares Class A Common Stock outstanding as reported in the Form 144 table

Approximate sale date September 18, 2026 Planned timing for sales under the Rule 144 notice

RSU vesting tranche 8,333 shares Vesting on September 1, 2021 from restricted stock unit awards

RSU vesting tranches 4,167 and 4,166 shares Multiple vesting events on November 5, 2021, February 5, 2022, May 5, 2022, and August 5, 2022

Key Terms

Rule 144, restricted stock unit awards, equity compensation plan

3 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 unit awards financial

"Vesting of restricted stock unit awards | Oscar Health, Inc."

Restricted stock unit awards are company promises to deliver a specific number of shares to employees or service providers in the future once conditions—such as staying with the company for a set time or meeting performance targets—are met. They matter to investors because when the promises convert into actual shares they increase the total share count and can reduce earnings per share, while also aligning recipients’ interests with stock performance much like deferred pay that turns into ownership if goals are met.

equity compensation plan financial

"Granted as part of issuer equity compensation plan"

A plan by which a company gives employees, directors or contractors ownership or the right to buy ownership in the company through stock, options or similar awards — think of promising slices of the company pie as part of someone's pay. It matters to investors because these awards can change the number of shares outstanding, affect reported profits and influence management’s decisions; large or generous plans can dilute existing holders and alter incentives over time.

FAQ

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

What does the Form 144 filing mean for Oscar Health, Inc. (OSCR)?

The Form 144 notice states that an officer of Oscar Health, Inc., Vanessa Wittman, plans to sell up to 25,000 shares of Class A Common Stock under Rule 144. This is a disclosure of a potential sale, not an execution report.

How many Oscar Health (OSCR) shares are covered by this Rule 144 notice?

The notice covers up to 25,000 shares of Oscar Health Class A Common Stock, with an aggregate market value reported as $806,000 in the Form 144 securities information table.

Who is selling shares of Oscar Health (OSCR) under this Form 144?

The planned sale is for the account of Vanessa Wittman, identified as an officer. The shares to be sold were acquired through vesting of restricted stock unit awards granted under Oscar Health’s equity compensation plan.

What is the proposed timing and venue of the Oscar Health (OSCR) share sale?

The Form 144 lists an approximate sale date of September 18, 2026, with sales to be executed through Merrill Lynch on the NYSE, according to the securities information section.

How many Oscar Health (OSCR) shares are reported as outstanding in this Form 144?

The Form 144 table reports 273,469 shares of Oscar Health Class A Common Stock as outstanding for the class referenced in the notice, alongside the 25,000 shares proposed for sale.

How were the Oscar Health (OSCR) shares being sold originally acquired?

The notice describes the shares as acquired through vesting of restricted stock unit awards, with tranches of 8,333 shares on September 1, 2021 and 4,167 or 4,166 shares vesting on several dates in 2021–2022, all granted under the issuer’s equity compensation plan.

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

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Available on EDGAR 09/18/2026 - 04:03 PM Accepted by SEC EDGAR 09/18/2026 - 04:02 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	0001229265
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	Oscar Health, Inc.
SEC File Number	001-40154
Address of Issuer	75 VARICK STREET 5TH FLOOR NEW YORK NEW YORK 10013
Phone	(646) 403-3677
Name of Person for Whose Account the Securities are To Be Sold	WITTMAN VANESSA AMES
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
Class A Common Stock	Merrill Lynch 225 Liberty Street Floor 37 New York NY 10281	25000	806000.00	273469	09/18/2026	NYSE

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 *
Class A Common Stock	09/01/2021	Vesting of restricted stock unit awards	Oscar Health, Inc.			8333	09/01/2021	Granted as part of issuer equity compensation plan
Class A Common Stock	11/05/2021	Vesting of restricted stock unit awards	Oscar Health, Inc.			4167	11/05/2021	Granted as part of issuer equity compensation plan
Class A Common Stock	02/05/2022	Vesting of restricted stock unit awards	Oscar Health, Inc.			4166	02/05/2022	Granted as part of issuer equity compensation plan
Class A Common Stock	05/05/2022	Vesting of restricted stock unit awards	Oscar Health, Inc.			4167	05/05/2022	Granted as part of issuer equity compensation plan
Class A Common Stock	08/05/2022	Vesting of restricted stock unit awards	Oscar Health, Inc.			4167	08/05/2022	Granted as part of issuer equity compensation plan

* 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

Nothing to Report

144: Remarks and Signature

Remarks
Date of Notice	09/18/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	06/18/2026
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	Vanessa Wittman
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)