Oscar Health officer plans sale of 28,869 shares

Oscar Health, Inc. (OSCR) received a notice that officer Richard Scott Blackley intends to sell 28,869 Class A shares of Oscar Health common stock under Rule 144.

Rhea-AI Filing Summary

Oscar Health, Inc. (OSCR) received a notice that officer Richard Scott Blackley intends to sell 28,869 Class A shares of Oscar Health common stock under Rule 144. The shares relate to restricted stock vesting on September 1, 2026, with a portion of the sale covering associated tax obligations.

Key Figures

Shares to be sold: 28,869 shares Aggregate market value: $907,950.27 Shares outstanding: 273,469,000 shares +2 more

5 metrics

Shares to be sold 28,869 shares Class A common stock covered by the Rule 144 notice

Aggregate market value $907,950.27 Reported value of the 28,869 Class A shares in the securities section

Shares outstanding 273,469,000 shares Class A shares outstanding referenced in the Form 144

Vesting date September 1, 2026 Restricted stock vesting date tied to the shares to be sold

Date of notice September 3, 2026 Date the Form 144 notice was filed

Key Terms

Rule 144, restricted stock vesting, vested equity award distribution

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 vesting financial

"Class A | 09/01/2026 | Restricted Stock Vesting | Issuer"

Restricted stock vesting is the timetable and conditions under which shares granted to employees or insiders become fully owned and can be sold, typically requiring continued work or meeting performance goals. It matters to investors because large blocks of shares can become tradable at once, which can change share supply and price, and because vesting aligns insiders’ incentives with the company’s long‑term performance—think of it like a timed unlock that both rewards and locks in key people.

vested equity award distribution financial

"resulting from the settlement of a vested equity award distribution."

FAQ

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

What does the Form 144 filing disclose for OSCR?

It discloses that officer Richard Scott Blackley intends to sell 28,869 Class A shares of Oscar Health, Inc. under Rule 144, related to restricted stock vesting on September 1, 2026, with part of the sale covering a tax obligation from the equity award settlement.

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

The notice covers 28,869 Class A shares of Oscar Health, Inc. These shares are tied to restricted stock vesting on September 1, 2026 and are to be sold through Fidelity Brokerage Services LLC on the NYSE.

What is the approximate market value of the Oscar Health (OSCR) shares in this Form 144?

The filing reports an aggregate market value of $907,950.27 for the 28,869 Class A shares covered by the notice, based on the price information used in the Form 144 securities section.

Why is part of Richard Scott Blackley’s OSCR share sale being made?

The remarks state the sale includes an amount necessary to cover a tax obligation resulting from the settlement of a vested equity award distribution, indicating that a portion of the shares is being sold to satisfy tax liabilities from the award vesting.

When are the Oscar Health (OSCR) securities scheduled to vest and be sold?

The Form 144 states the Class A shares relate to restricted stock vesting on September 1, 2026. The notice date is September 3, 2026, and the securities are listed for sale on the NYSE through Fidelity Brokerage Services LLC.

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

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Available on EDGAR 09/03/2026 - 03:22 PM EDT Accepted by SEC EDGAR 09/03/2026 - 03:22 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	0001525020
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	Blackley Richard Scott
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	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	28869	907950.27	273469000	09/03/2026	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	09/01/2026	Restricted Stock Vesting	Issuer			28869	09/01/2026	Compensation

* 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	Sale includes an amount necessary to cover a tax obligation resulting from the settlement of a vested equity award distribution.
Date of Notice	09/03/2026
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/ Joshua Schmitt, as a duly authorized representative of Fidelity Brokerage Services LLC, as attorney-in-fact for Richard Scott Blackley.
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)