Oscar Health (OSCR) CFO lines up new stock sale after recent $2.75M sale

Rhea-AI Filing Summary

Oscar Health, Inc. (OSCR) is the issuer in a notice filed under Rule 144 covering planned sales of its common stock for the account of Chief Financial Officer Richard Scott Blackley, with Morgan Stanley Private Wealth Management listed as broker. The notice lists 18,750 shares of common stock to be sold and references restricted stock units vesting under a registered plan on 03/01/2024 and 12/01/2024. Recent activity disclosed includes multiple common stock sales during May and June 2026, and a remark states that certain shares were sold by the MQB Irrevocable Trust, with the notice signed by an attorney-in-fact for Blackley.

Key Figures

Shares to be sold: 18,750 shares RSUs vesting 12/01/2024: 14,498 shares RSUs vesting 03/01/2024: 7,015 shares +5 more

8 metrics

Shares to be sold 18,750 shares Common stock indicated for sale with Morgan Stanley Private Wealth Management

RSUs vesting 12/01/2024 14,498 shares Restricted stock units vesting under a registered plan for services rendered

RSUs vesting 03/01/2024 7,015 shares Restricted stock units vesting under a registered plan for services rendered

Sale on 05/14/2026 91,259 shares for $2,108,082.90 Common stock sold for account of Richard Scott Blackley

Additional sale on 05/14/2026 8,741 shares for $207,948.39 Second common stock sale on the same date

Sale on 05/18/2026 110,000 shares for $2,753,300.00 Common stock sale reported for Richard Scott Blackley

Sale on 06/02/2026 22,706 shares for $493,628.44 Common stock sale reported for Richard Scott Blackley

Additional sale on 06/02/2026 8,977 shares for $201,533.65 Second common stock sale on that date

Key Terms

Rule 144, restricted stock units, irrevocable trust, services rendered

4 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 units financial

"Restricted stock units vesting under a registered plan"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

irrevocable trust financial

"Remarks | Shares sold by MQB Irrevocable Trust"

An irrevocable trust is a legal arrangement where an owner transfers assets into a separate entity managed by a trustee and gives up the power to modify or reclaim those assets. For investors it matters because putting stock or other holdings into such a trust can change who controls and benefits from the assets, affect taxes and creditor protection, and influence how easy it is to sell or value those holdings—like placing valuables in a locked safe overseen by someone else.

services rendered financial

"12/01/2024 | Services Rendered"

FAQ

What does the Form 144 filing disclose about Oscar Health, Inc. (OSCR)?

The filing discloses a planned sale of 18,750 shares of Oscar Health, Inc. common stock under Rule 144 for CFO Richard Scott Blackley, and lists prior common stock sales in May and June 2026 by an associated trust.

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

The notice covers a proposed sale of 18,750 shares of Oscar Health, Inc. common stock. It also references restricted stock units vesting on 03/01/2024 and 12/01/2024 under a registered plan as sources of the stock.

Who is the insider involved in the Oscar Health (OSCR) Form 144 filing?

The person for whose account securities are to be sold is Richard Scott Blackley, identified as Officer – CFO of Oscar Health, Inc. The document notes that certain shares were sold by the MQB Irrevocable Trust associated with him.

Which broker is handling the planned Oscar Health (OSCR) stock sale in this Form 144?

The planned sale of Oscar Health, Inc. common stock is listed through Morgan Stanley Private Wealth Management, located at 555 California Street, San Francisco, California. This firm appears as the broker for the 18,750 shares indicated.

What recent Oscar Health (OSCR) stock sales are reported for Richard Scott Blackley?

Recent common stock sales include 91,259 shares for $2,108,082.90 and 8,741 shares for $207,948.39 on 05/14/2026, plus additional transactions on 05/18/2026 and 06/02/2026 with specified share counts and dollar amounts.

What restricted stock unit vesting events are tied to Oscar Health (OSCR) in this filing?

The filing cites restricted stock units vesting under a registered plan on 03/01/2024 covering 7,015 shares and on 12/01/2024 covering 14,498 shares, both described as issued by the issuer for services rendered.

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Available on EDGAR 08/18/2026 - 04:56 PM Accepted by SEC EDGAR 08/18/2026 - 04:56 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	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	Richard Scott Blackley
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 - CFO

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 Stock	Morgan Stanley Private Wealth Management 555 California Street, 14th Floor San Francisco CA 94104	18750	614250	273469000	08/18/2026	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 *
Common Stock	12/01/2024	Restricted stock units vesting under a registered plan	Issuer			14498	12/01/2024	Services Rendered
Common Stock	03/01/2024	Restricted stock units vesting under a registered plan	Issuer			7015	03/01/2024	Services Rendered

* 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
Richard Scott Blackley 75 Varick Street, 5th Floor New York NY 10013	Common Stock	05/14/2026	91259	2108082.90
Richard Scott Blackley 75 Varick Street, 5th Floor New York NY 10013	Common Stock	05/14/2026	8741	207948.39
Richard Scott Blackley 75 Varick Street, 5th Floor New York NY 10013	Common Stock	05/18/2026	110000	2753300.00
Richard Scott Blackley 75 Varick Street, 5th Floor New York NY 10013	Common Stock	06/02/2026	22706	493628.44
Richard Scott Blackley 75 Varick Street, 5th Floor New York NY 10013	Common Stock	06/02/2026	8977	201533.65

144: Remarks and Signature

Remarks	Shares sold by MQB Irrevocable Trust
Date of Notice	08/18/2026
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	Melissa Curtin, Attorney-in-Fact for Richard Scott Blackley
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)