Oscar Health (NYSE: OSCR) ex-affiliate plans multi-million stock sale

Rhea-AI Filing Summary

Oscar Health, Inc. (OSCR) received a notice that former affiliate Jeffery H. Boyd plans to sell up to 288,514 shares of Oscar common stock under Rule 144. The shares, to be sold on 11/12/2024, come from previously exercised options and are to be sold for cash through Morgan Stanley Smith Barney LLC.

The notice also lists prior Rule 144 sales of Oscar common stock by Boyd during the past three months, providing regulators and the market with transparency on recent and proposed share dispositions.

Key Figures

Shares to be sold: 288,514 shares Aggregate market value of shares to be sold: $9,564,296.80 Shares outstanding: 273,469,000 shares +4 more

7 metrics

Shares to be sold 288,514 shares Common stock proposed for sale under Rule 144

Aggregate market value of shares to be sold $9,564,296.80 Value for 288,514 shares of Oscar Health common stock

Shares outstanding 273,469,000 shares Oscar Health common stock referenced in the securities information section

Proposed sale date 11/12/2024 Date for sale of 288,514 shares from previously exercised options

Past sale 1 288,513 shares for $8,687,790.01 Common stock sold by Jeffery H. Boyd on 08/13/2026

Past sale 2 134,370 shares for $3,799,231.13 Common stock sold by Jeffery H. Boyd on 08/10/2026

Past sale 3 116,666 shares for $3,281,651.25 Common stock sold by Jeffery H. Boyd on 08/10/2026

Key Terms

Rule 144, Former Affiliate, Previously Exercised Options

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.

Former Affiliate regulatory

"Former Affiliate 144: Securities Information"

Previously Exercised Options financial

"Common | 11/12/2024 | Previously Exercised Options | Issuer"

FAQ

What does the Form 144 involving Oscar Health (OSCR) and Jeffery H. Boyd disclose?

It discloses that former affiliate Jeffery H. Boyd intends to sell up to 288,514 shares of Oscar Health common stock on 11/12/2024 for cash, with the shares coming from previously exercised options and the sale to be executed through Morgan Stanley Smith Barney LLC.

How many Oscar Health (OSCR) shares are proposed to be sold under this Form 144?

The filing states that up to 288,514 shares of Oscar Health common stock are to be sold under Rule 144. These shares are associated with previously exercised options and are planned to be sold for cash on 11/12/2024.

What is the reported market value of the Oscar Health (OSCR) shares covered by this Form 144?

The filing reports an aggregate market value of approximately $9,564,296.80 for the 288,514 Oscar Health common shares covered by the notice, based on the information provided in the securities information section.

What prior Oscar Health (OSCR) stock sales by Jeffery H. Boyd are disclosed?

The notice lists past three months’ sales of Oscar common stock by Jeffery H. Boyd, including 288,513 shares on 08/13/2026 for $8,687,790.01, 134,370 shares on 08/10/2026 for $3,799,231.13, and 116,666 shares on 08/10/2026 for $3,281,651.25.

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

The Form 144 references 273,469,000 shares of Oscar Health common stock outstanding. This figure is provided as part of the securities information and serves as context for the proposed sale under Rule 144.

Through which broker are the proposed Oscar Health (OSCR) shares to be sold?

The proposed sale of 288,514 Oscar Health common shares is to be executed through Morgan Stanley Smith Barney LLC Executive Financial Services, located at 1 New York Plaza, 8th Floor, New York, NY 10004, according to the securities information section.

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

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Available on EDGAR 08/20/2026 - 04:08 PM Accepted by SEC EDGAR 08/20/2026 - 04:08 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	0001214606
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	6464033677
Name of Person for Whose Account the Securities are To Be Sold	JEFFERY H. BOYD
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	Former Affiliate

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	288514	9564296.80	273469000	08/20/2026	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 *
Common	11/12/2024	Previously Exercised Options	Issuer			288514	11/12/2024	Cash

* 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
JEFFERY H. BOYD 75 Varick Street, 5th Floor New York NY 10013	Common	08/13/2026	288513	8687790.01
JEFFERY H. BOYD 75 Varick Street, 5th Floor New York NY 10013	Common	08/10/2026	134370	3799231.13
JEFFERY H. BOYD 75 Varick Street, 5th Floor New York NY 10013	Common	08/10/2026	116666	3281651.25

144: Remarks and Signature

Remarks
Date of Notice	08/20/2026
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/ Jeffery Boyd
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)