Were Mark Bertolini’s June 2026 Oscar Health (OSCR) share sales pre-planned?

Yes. The Form 4 discloses that the tax-related share sales were effected under a Rule 10b5-1 instruction letter. That instruction letter was originally entered into on November 10, 2025 and amended and restated on March 24, 2026 before the reported transactions.

Do Mark Bertolini’s Oscar Health (OSCR) share sales indicate a change in his ownership stance?

The filing characterizes the sales as driven by tax withholding for vested stock units, not as discretionary portfolio moves. Bertolini remains a large shareholder, directly owning at least 8,990,566 shares after the transactions, suggesting an ongoing substantial equity interest in Oscar Health.

Oscar Health (OSCR) CEO Mark Bertolini sells 1.2M shares for tax obligations

Filing Impact

(Very High)

Filing Sentiment

(Very Negative)

Form Type

Rhea-AI Filing Summary

Oscar Health, Inc. CEO Mark T. Bertolini reported open-market sales of a total of 1,206,310 shares of Class A common stock on June 25–26, 2026 at weighted average prices ranging from $28.06 to $30.17 per share. According to the filing, these transactions represent sales to satisfy tax withholding obligations related to the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026, and were effected pursuant to a pre-arranged Rule 10b5-1 instruction letter. Following these transactions, Bertolini continues to hold at least 8,990,566 shares of Class A common stock directly.

Insights

CEO’s sales are tied to tax withholding under a pre-set 10b5-1 plan.

Mark T. Bertolini, CEO of Oscar Health, Inc., reported selling 1,206,310 shares of Class A common stock in open-market transactions at prices around $28–$30 per share. The filing explains these sales were to cover tax obligations from vested performance and restricted stock units.

The use of a Rule 10b5-1 instruction letter, entered into and later amended before these trades, indicates the sales were pre-planned rather than timed opportunistically. After the transactions, he still directly holds at least 8,990,566 shares, suggesting a substantial remaining equity stake.

Because the activity is tied to equity award vesting and tax withholding rather than discretionary portfolio changes, and the CEO retains a large position, this filing generally signals routine compensation-related administration rather than a shift in outlook. Market impact depends more on overall float and trading liquidity than on this single event.

Insider Trade Summary 10b5-1

Net Seller: 1,206,310 shares ($34,912,078)

Net Sell 4 txns

Insider Bertolini Mark T

Role Chief Executive Officer

Sold 1,206,310 shs ($34.91M)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	441,373	$29.11	$12.85M
Sale	Class A Common Stock	149,795	$29.79	$4.46M
Sale	Class A Common Stock	597,942	$28.60	$17.10M
Sale	Class A Common Stock	17,200	$29.08	$500K

Holdings After Transaction: Class A Common Stock — 9,140,361 shares (Direct, null)

Footnotes (1)

Represents sale of shares to satisfy tax withholding obligations in connection with the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.06 to $29.05, 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 $29.06 to $29.19, 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. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.51 to $29.50, 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. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.51 to $30.17, 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

Total shares sold: 1,206,310 shares Representative sale price: $29.79 per share Representative sale price: $29.11 per share +4 more

7 metrics

Total shares sold 1,206,310 shares Open-market sales on June 25–26, 2026

Representative sale price $29.79 per share One June 26, 2026 transaction in Class A common stock

Representative sale price $29.11 per share Another June 26, 2026 open-market sale

Post-transaction holdings 8,990,566 shares Minimum direct Class A common stock held after reported sales

Tax-related vesting date April 3, 2026 Vesting date of performance and restricted stock units

10b5-1 instruction entry date November 10, 2025 Original Rule 10b5-1 instruction letter for the sales

10b5-1 amendment date March 24, 2026 Amended and restated Rule 10b5-1 instruction letter

Key Terms

Rule 10b5-1 instruction letter, performance stock units, restricted stock units, weighted average price, +1 more

5 terms

Rule 10b5-1 instruction letter regulatory

"The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026."

performance stock units financial

"in connection with the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026."

Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.

restricted stock units financial

"in connection with the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026."

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. These shares were sold in multiple transactions at prices ranging from $28.06 to $29.05, inclusive."

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.

tax withholding obligations financial

"Represents sale of shares to satisfy tax withholding obligations in connection with the deferred settlement of performance stock units and time-based restricted stock units."

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 06/29/2026 - 04:17 PM Accepted by SEC EDGAR 06/29/2026 - 04:17 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^*

Bertolini Mark T

(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)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/25/2026

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	06/25/2026		S⁽¹⁾		597,942	D	$28.6⁽²⁾	9,598,934⁽³⁾	D
Class A Common Stock	06/25/2026		S⁽¹⁾		17,200	D	$29.08⁽⁴⁾	9,581,734⁽³⁾	D
Class A Common Stock	06/26/2026		S⁽¹⁾		441,373	D	$29.11⁽⁵⁾	9,140,361⁽³⁾	D
Class A Common Stock	06/26/2026		S⁽¹⁾		149,795	D	$29.79⁽⁶⁾	8,990,566⁽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. Represents sale of shares to satisfy tax withholding obligations in connection with the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026. The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on November 10, 2025 and amended and restated on March 24, 2026.

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.06 to $29.05, 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 $29.06 to $29.19, 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.

5. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.51 to $29.50, 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.

6. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.51 to $30.17, 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	06/29/2026
	** 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 did Oscar Health (OSCR) CEO Mark Bertolini report in this Form 4?

Oscar Health CEO Mark T. Bertolini reported selling 1,206,310 shares of Class A common stock. These open-market sales occurred on June 25–26, 2026, at weighted average prices in the high-$20s to about $30 per share, according to the Form 4 filing.

Why did Oscar Health (OSCR) CEO Mark Bertolini sell shares in June 2026?

The filing states the sales were made to satisfy tax withholding obligations. They relate to the deferred settlement of performance stock units and time-based restricted stock units that vested on April 3, 2026, making the transactions part of routine equity-compensation tax management.

How many Oscar Health (OSCR) shares does CEO Mark Bertolini hold after these sales?

After completing the reported transactions, Mark Bertolini continues to directly hold at least 8,990,566 shares of Oscar Health Class A common stock. This figure reflects the lowest post-transaction share balance disclosed for the June 2026 sales in the Form 4.

At what prices did Mark Bertolini sell Oscar Health (OSCR) shares in June 2026?

The Form 4 reports weighted average sale prices around $28–$30 per share. Footnotes note multiple trades, with sale prices ranging from $28.06 to $30.17 per share, and offer to provide full breakdowns of share counts at each separate execution price upon request.