Was the Oscar Health (OSCR) CFO’s share sale under a Rule 10b5-1 plan?

Yes. The filing states the transaction was executed under a Rule 10b5-1 trading plan adopted on February 12, 2026. Such plans pre-schedule trades, indicating the sale timing was arranged in advance rather than being an opportunistic market decision.

How large was the net share change in this Oscar Health (OSCR) insider filing?

The filing shows a net disposition of 110,000 Oscar Health Class A shares through an open-market sale. No option exercises, gifts, tax withholdings, or derivative transactions were reported, and the remaining direct and indirect holdings are disclosed after the transaction.

CFO’s 110,000-share Oscar Health (NYSE: OSCR) sale is pre-planned

Filing Impact

(Very High)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Oscar Health Chief Financial Officer Richard Scott Blackley sold 110,000 shares of Class A Common Stock in an open-market transaction at a weighted average price of $25.03 per share. The sale was carried out pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026, indicating it was pre-arranged. After the sale, he holds 1,106,660 shares directly, and an additional 75,000 shares are held indirectly by the MQB Irrevocable Trust, which includes shares to be issued upon vesting of restricted stock units.

Insider Trade Summary 10b5-1

Net Seller: 110,000 shares ($2,753,300)

Net Sell 2 txns

Insider Blackley Richard Scott

Role Chief Financial Officer

Sold 110,000 shs ($2.75M)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	110,000	$25.03	$2.75M
holding	Class A Common Stock	--	--	--

Holdings After Transaction: Class A Common Stock — 1,106,660 shares (Direct, null); Class A Common Stock — 75,000 shares (Indirect, By MQB Irrevocable Trust)

Footnotes (1)

The transaction was effected pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $25.00 to $25.20 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.

Key Figures

Shares sold: 110,000 shares Weighted average sale price: $25.03 per share Post-sale direct holdings: 1,106,660 shares +2 more

5 metrics

Shares sold 110,000 shares Open-market sale of Class A Common Stock

Weighted average sale price $25.03 per share Class A Common Stock sale on May 18, 2026

Post-sale direct holdings 1,106,660 shares Class A Common Stock held directly after transaction

Indirect trust holdings 75,000 shares Held by MQB Irrevocable Trust, includes RSU vesting

Sale price range $25.00–$25.20 per share Multiple trades aggregated into weighted average price

Key Terms

Rule 10b5-1 trading plan, weighted average price, restricted stock units, MQB Irrevocable Trust

4 terms

Rule 10b5-1 trading plan financial

"The transaction was effected pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026."

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

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.

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.

MQB Irrevocable Trust financial

"nature_of_ownership: By MQB Irrevocable Trust"

Form 4 Insider Transactions: What Each Field Means →

05/20/2026 - 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^*

Blackley Richard Scott

(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 Financial Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/18/2026

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	05/18/2026		S		110,000⁽¹⁾	D	$25.03⁽²⁾	1,106,660⁽³⁾	D
Class A Common Stock								75,000	I	By MQB Irrevocable Trust

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 transaction was effected pursuant to a Rule 10b5-1 trading plan adopted on February 12, 2026.

2. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $25.00 to $25.20 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.

Remarks:

	/s/ Melissa Curtin, Attorney-in-fact	05/20/2026
	** 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 its CFO?

Oscar Health reported that CFO Richard Scott Blackley sold 110,000 shares of Class A Common Stock. The shares were sold in an open-market transaction at a weighted average price of $25.03 per share, according to a recent Form 4 insider filing.

At what price did the Oscar Health (OSCR) CFO sell his shares?

The CFO sold 110,000 Oscar Health shares at a weighted average price of $25.03. Footnotes explain these were multiple trades executed between $25.00 and $25.20 per share, with detailed breakdowns available upon request from the company or regulators.

How many Oscar Health (OSCR) shares does the CFO hold after this sale?

After the sale, the CFO directly holds 1,106,660 Oscar Health Class A shares. An additional 75,000 shares are held indirectly by the MQB Irrevocable Trust, which also includes shares to be issued as restricted stock units vest over time.

What does the MQB Irrevocable Trust hold for the Oscar Health (OSCR) CFO?

The MQB Irrevocable Trust holds 75,000 Oscar Health Class A shares associated with the CFO’s indirect ownership. Footnotes clarify this amount includes shares that will be issued as one or more restricted stock units vest in the future.