September 18, 2026 - 144: Report of proposed sale of securities

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	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

Form: 144

FORM 144