Was Adam McAnaney’s Oscar Health (OSCR) share sale part of a Rule 10b5-1 plan?

Yes. The filing states the sales were effected under a Rule 10b5-1 instruction letter entered into on August 8, 2025. This plan was designed to satisfy his tax withholding obligations tied to vesting equity awards.

Oscar Health (OSCR) legal chief sells 9,859 shares under 10b5-1 plan

Filing Impact

(Moderate)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Oscar Health, Inc. Chief Legal Officer Adam McAnaney reported selling a total of 9,859 shares of Class A common stock in two open-market transactions. One sale covered 2,794 shares at a weighted average price of about $22.45 per share, and the other covered 7,065 shares at about $21.74 per share. According to the disclosure, these sales were carried out under a pre-arranged Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy tax withholding obligations upon the vesting of previously granted equity awards. The prices reflected multiple trades within ranges of $21.03 to $22.02 and $22.03 to $22.96 per share.

Insider Trade Summary 10b5-1

Net Seller: 9,859 shares ($216,318)

Net Sell 2 txns

Insider McAnaney Adam

Role Chief Legal Officer

Sold 9,859 shs ($216K)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	7,065	$21.74	$154K
Sale	Class A Common Stock	2,794	$22.45	$63K

Holdings After Transaction: Class A Common Stock — 220,890 shares (Direct, null)

Footnotes (1)

The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.03 to $22.02, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected. Includes shares to be issued in connection with the vesting of one or more restricted stock units. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.03 to $22.96, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

Key Figures

Shares sold (trade 1): 2,794 shares Shares sold (trade 2): 7,065 shares Total shares sold: 9,859 shares +2 more

5 metrics

Shares sold (trade 1) 2,794 shares Open-market sale of Class A common stock at about $22.45 per share on June 2, 2026

Shares sold (trade 2) 7,065 shares Open-market sale of Class A common stock at about $21.74 per share on June 2, 2026

Total shares sold 9,859 shares Net-sell shares across two open-market transactions reported in the filing

Price range (lower block) $21.03–$22.02 per share Range of individual trade prices for one weighted-average sale

Price range (upper block) $22.03–$22.96 per share Range of individual trade prices for the other weighted-average sale

Key Terms

Rule 10b5-1, restricted stock units, weighted average price

3 terms

Rule 10b5-1 regulatory

"The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025"

Rule 10b5-1 is a regulation that allows company insiders to buy or sell their shares at predetermined times, even if they have access to non-public information. It acts like setting a schedule in advance for transactions, helping prevent accusations of unfair trading. This rule provides a way for insiders to plan trades transparently, giving investors confidence that these transactions are not based on hidden information.

restricted stock units financial

"Includes shares to be issued in connection with the vesting of one or more restricted stock units."

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.

weighted average price financial

"The price reported in Column 4 is a weighted average price."

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

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Form 4 Insider Transactions: What Each Field Means →

06/04/2026 - 04:16 PM

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

McAnaney Adam

(Last)

(First)

(Middle)

75 VARICK STREET, 5TH FLOOR

(Street)

NEW YORK

10013

(City)

(State)

(Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Oscar Health, Inc. [ OSCR ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	Chief Legal Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/02/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock	06/02/2026		S		7,065⁽¹⁾	D	$21.74⁽²⁾	220,890⁽³⁾	D
Class A Common Stock	06/02/2026		S		2,794⁽¹⁾	D	$22.45⁽⁴⁾	218,096⁽³⁾	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

Explanation of Responses:

1. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards.

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $21.03 to $22.02, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

3. Includes shares to be issued in connection with the vesting of one or more restricted stock units.

4. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $22.03 to $22.96, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

Remarks:

	/s/ Melissa Curtin, Attorney-in-fact	06/04/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transaction did Oscar Health (OSCR) report for Adam McAnaney?

Oscar Health reported that Chief Legal Officer Adam McAnaney sold 9,859 shares of Class A common stock in two open-market transactions. These trades were executed on June 2, 2026 as part of a pre-arranged Rule 10b5-1 instruction letter.

At what prices did Adam McAnaney sell Oscar Health (OSCR) shares?

Adam McAnaney’s reported sales used weighted average prices of about $22.45 and $21.74 per share. Footnotes explain the individual trades occurred within ranges of $21.03 to $22.02 and $22.03 to $22.96 per share, respectively.

How many Oscar Health (OSCR) shares did Adam McAnaney sell in each trade?

Adam McAnaney sold 2,794 shares in one transaction and 7,065 shares in another, totaling 9,859 shares. Both transactions involved Oscar Health Class A common stock and were reported as open-market sales on June 2, 2026.

Why did Oscar Health’s (OSCR) Chief Legal Officer sell shares?

The disclosure explains that Adam McAnaney’s sales were intended to satisfy his tax withholding obligations from the vesting of previously granted equity awards. The transactions were executed automatically under a Rule 10b5-1 instruction letter, rather than as discretionary market-timing trades.

How many total shares did Adam McAnaney net-sell of Oscar Health (OSCR)?

Across the reported transactions, Adam McAnaney net-sold 9,859 shares of Oscar Health Class A common stock. The filing’s transaction summary characterizes this activity as two open-market sales with a combined net-sell share count of 9,859.