OSCR SEC Filing News — Oscar Health, Inc.

Latest SEC filings for Oscar Health, Inc. (OSCR) explained in plain English. Covers insider buying and selling (Form 4), proposed insider sales (Form 144), material company events (8-K), and quarterly & annual reports (10-Q / 10-K). StrongBuyAnalytics provides navigation and brief excerpts or summaries; original filings remain at the SEC/source links and were authored by their filers, not StrongBuyAnalytics. Filing dates shown are source dates. Coverage and detection can be delayed or incomplete because of SEC availability, amendments, parsing, caching, or outages. Latest source filing date shown: 2026-09-22.

Oscar Health, Inc. operates as a healthcare technology company in the United States. The company offers health plans to individuals, families, employees, and small group markets. It also provides +Oscar platform that power others throughout the healthcare system; Campaign Builder platform, an engagement and recommendation platform for providers and payors; and reinsurance products. In addition, the company offers brokerage services and enrollment platform for brokers and consumers to shop, buy, …
Sector: Healthcare Industry: Healthcare Plans Market Cap: $10.0B CIK: 1568651
20
Total Filings
0
Bullish Classifications
10
Bearish Classifications
10
Insider Transactions
1
Material Events (8-K)
0
Periodic Reports
Rule-based classifications for OSCR currently lean bearish. Of the 20 filing records displayed, 10 carry bearish classifications (such as insider sales or negative 8-K disclosures) versus 0 bullish. This does not necessarily signal fundamental deterioration — insiders sell for many reasons — but it is worth monitoring alongside the company's core financial metrics.
OSCR Filing Activity Snapshot 2026-08-18 — 2026-09-22
Insider Transactions (Form 4)
0 buys vs 8 sells
Net insider selling in this period — insiders sell for many reasons beyond conviction.
Largest Form 144 Filing
$22.82M
Schlosser Mario (Director) · 2026-08-31
750,000 shares · Form 4
Form 144 Notices
9
Proposed insider sales filed — Form 144 is a notice of intent, not a confirmed transaction. Actual sales are confirmed via Form 4.
Insider Transactions 10 · Forms 3, 4 and 5

A Form 4 is filed within two business days of a company insider — an officer, a director, or a holder of more than ten percent of the stock — changing their position in the shares. All 10 filings in this group are Form 4s for Oscar Health, Inc.

The difficulty with reading these filings as a group is that a single form type covers transactions that mean entirely different things. An executive spending their own money to buy stock and an executive having shares withheld to pay tax on a vesting grant both appear as a Form 4. Every filing below is therefore tagged with the nature of the underlying transaction, taken from the transaction code reported on the form itself.

Across the 10 insider filings shown, the breakdown is 8 open-market sale and 2 other reported transaction. 8 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.

What each transaction type means

Open-market sale ×8
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Other reported transaction ×2
The filing reports a transaction type that does not map to a routine purchase, sale, award or withholding.
Form 4 Open-market sale Insider Selling 2026-09-22

OSCR insider WITTMAN VANESSA AMES (Director) sold 25,000 shares (~$806.0K)

WITTMAN VANESSA AMES, listed as Director at Oscar Health, Inc., reported an open-market sale of 25,000 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 25,000 $32.24 $806.0K
Filing: Form 4 (Insider Transaction) Insider: WITTMAN VANESSA AMES (Director) Shares: 25,000 Est. Value: $806.0K
View on SEC EDGAR → Open Filing Document →
Form 4 Other reported transaction Tax / Compensation Filing 2026-09-18

OSCR insider Form 4 filed for equity award, exercise, or tax withholding

Kushner Joshua (Director, Co-Founder and Vice Chairman, 10% Owner) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The filing reports a transaction type that does not map to a routine purchase, sale, award or withholding.

Transactions reported on this filing
Code Nature Shares Price Value
J Other transaction 6,268,097 — —
J Other transaction 75,520 — —
J Other transaction 1,323,589 — —
J Other transaction 4,855,810 — —
J Other transaction 164,218 — —
J Other transaction 1,323,589 — —
J Other transaction 4,855,810 — —
J Other transaction 164,218 — —
J Other transaction derivative · Class B Common Stock 1,323,589 — —
J Other transaction derivative · Class B Common Stock 4,855,810 — —
J Other transaction derivative · Class B Common Stock 164,218 — —
J Other transaction derivative · Class B Common Stock 6,268,097 — —
J Other transaction derivative · Class B Common Stock 75,520 — —
Filing: Form 4 (Insider Transaction) Insider: Kushner Joshua (Director, Co-Founder and Vice Chairman, 10% Owner) Shares: 19,030,851
View on SEC EDGAR → Open Filing Document →
Form 4 Other reported transaction Tax / Compensation Filing 2026-09-18

OSCR insider Form 4 filed for equity award, exercise, or tax withholding

Thrive Partners II GP, LLC (Director, 10% Owner) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The filing reports a transaction type that does not map to a routine purchase, sale, award or withholding.

Transactions reported on this filing
Code Nature Shares Price Value
J Other transaction 6,268,097 — —
J Other transaction 75,520 — —
J Other transaction 1,323,589 — —
J Other transaction 4,855,810 — —
J Other transaction 164,218 — —
J Other transaction 1,323,589 — —
J Other transaction 4,855,810 — —
J Other transaction 164,218 — —
J Other transaction derivative · Class B Common Stock 1,323,589 — —
J Other transaction derivative · Class B Common Stock 4,855,810 — —
J Other transaction derivative · Class B Common Stock 164,218 — —
J Other transaction derivative · Class B Common Stock 6,268,097 — —
J Other transaction derivative · Class B Common Stock 75,520 — —
Filing: Form 4 (Insider Transaction) Insider: Thrive Partners II GP, LLC (Director, 10% Owner) Shares: 19,030,851
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-08

OSCR insider Liang Janet (President, Oscar Insurance) sold 10,360 shares (~$325.8K)

Liang Janet, listed as President, Oscar Insurance at Oscar Health, Inc., reported an open-market sale of 10,360 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 10,360 $31.45 $325.8K
Filing: Form 4 (Insider Transaction) Insider: Liang Janet (President, Oscar Insurance) Shares: 10,360 Est. Value: $325.8K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-08

OSCR insider Baltrus Victoria (Chief Accounting Officer) sold 958 shares (~$30.1K)

Baltrus Victoria, listed as Chief Accounting Officer at Oscar Health, Inc., reported an open-market sale of 958 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 958 $31.45 $30.1K
Filing: Form 4 (Insider Transaction) Insider: Baltrus Victoria (Chief Accounting Officer) Shares: 958 Est. Value: $30.1K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-08

OSCR insider Blackley Richard Scott (Chief Financial Officer) sold 28,869 shares (~$907.9K)

Blackley Richard Scott, listed as Chief Financial Officer at Oscar Health, Inc., reported an open-market sale of 28,869 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 28,869 $31.45 $907.9K
Filing: Form 4 (Insider Transaction) Insider: Blackley Richard Scott (Chief Financial Officer) Shares: 28,869 Est. Value: $907.9K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-08

OSCR insider McAnaney Adam (Chief Legal Officer) sold 9,092 shares (~$285.9K)

McAnaney Adam, listed as Chief Legal Officer at Oscar Health, Inc., reported an open-market sale of 9,092 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 9,092 $31.45 $285.9K
Filing: Form 4 (Insider Transaction) Insider: McAnaney Adam (Chief Legal Officer) Shares: 9,092 Est. Value: $285.9K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-09-08

OSCR insider Schlosser Mario (Director) sold 31,422 shares (~$988.2K)

Schlosser Mario, listed as Director at Oscar Health, Inc., reported an open-market sale of 31,422 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 31,422 $31.45 $988.2K
Filing: Form 4 (Insider Transaction) Insider: Schlosser Mario (Director) Shares: 31,422 Est. Value: $988.2K
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-08-31

OSCR insider Schlosser Mario (Director) sold 750,000 shares (~$22.82M)

Schlosser Mario, listed as Director at Oscar Health, Inc., reported an open-market sale of 750,000 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
C Derivative conversion 600,000 — —
S Open-market sale 600,000 $30.34 $18.20M
C Derivative conversion 150,000 — —
S Open-market sale 150,000 $30.79 $4.62M
M Option exercise derivative · Stock Option (Right to Buy) 600,000 — —
M Option exercise derivative · Class B Common Stock 600,000 $9.75 $5.85M
C Derivative conversion derivative · Class B Common Stock 600,000 — —
M Option exercise derivative · Stock Option (Right to Buy) 150,000 — —
M Option exercise derivative · Class B Common Stock 150,000 $9.75 $1.46M
C Derivative conversion derivative · Class B Common Stock 150,000 — —
Filing: Form 4 (Insider Transaction) Insider: Schlosser Mario (Director) Shares: 750,000 Est. Value: $22.82M
View on SEC EDGAR → Open Filing Document →
Form 4 Open-market sale Insider Selling 2026-08-20

OSCR insider Blackley Richard Scott (Chief Financial Officer) sold 18,750 shares (~$595.1K)

Blackley Richard Scott, listed as Chief Financial Officer at Oscar Health, Inc., reported an open-market sale of 18,750 OSCR shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.

The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.

Transactions reported on this filing
Code Nature Shares Price Value
S Open-market sale 18,750 $31.74 $595.1K
Filing: Form 4 (Insider Transaction) Insider: Blackley Richard Scott (Chief Financial Officer) Shares: 18,750 Est. Value: $595.1K
View on SEC EDGAR → Open Filing Document →
Proposed Insider Sales 9 · Form 144

A Form 144 is a notice of intent to sell restricted or control securities. It is not a record that anything was sold. Oscar Health, Inc. has 9 such notices in this period.

The distinction matters because a Form 144 is frequently reported as though it were a completed insider sale. The filer may sell all of the shares covered, some of them, or none at all, and there is no obligation to update the notice either way. A sale that is actually executed by an officer or director shows up separately on a Form 4, which is the filing to check before treating a proposed sale as a real one.

Form 144 Proposed Insider Sale 2026-09-18

OSCR Form 144 filed for proposed insider sale by WITTMAN VANESSA AMES (25,000 shares) ~$806.0K

WITTMAN VANESSA AMES filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: WITTMAN VANESSA AMES Shares: 25,000 Est. Value: $806.0K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-09-03

OSCR Form 144 filed for proposed insider sale by McAnaney Adam (9,092 shares) ~$285.9K

McAnaney Adam filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: McAnaney Adam Shares: 9,092 Est. Value: $285.9K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-09-03

OSCR Form 144 filed for proposed insider sale by Schlosser Mario (31,422 shares) ~$988.2K

Schlosser Mario filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Schlosser Mario Shares: 31,422 Est. Value: $988.2K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-09-03

OSCR Form 144 filed for proposed insider sale by Liang Janet (10,360 shares) ~$325.8K

Liang Janet filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Liang Janet Shares: 10,360 Est. Value: $325.8K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-09-03

OSCR Form 144 filed for proposed insider sale by Blackley Richard Scott (28,869 shares) ~$908.0K

Blackley Richard Scott filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Blackley Richard Scott Shares: 28,869 Est. Value: $908.0K
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-08-28

OSCR Form 144 filed for proposed insider sale by Schlosser Mario (150,000 shares) ~$4.62M

Schlosser Mario filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Schlosser Mario Shares: 150,000 Est. Value: $4.62M
View on SEC EDGAR → Open Filing Document →
Form 144 Large Proposed Insider Sale 2026-08-27

OSCR Form 144 filed for proposed insider sale by Schlosser Mario (600,000 shares) ~$18.21M

Schlosser Mario filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4. The proposed dollar value is large enough to merit attention.

Filing: Form 144 (Proposed Sale Notice) Insider: Schlosser Mario Shares: 600,000 Est. Value: $18.21M
View on SEC EDGAR → Open Filing Document →
Form 144 Large Proposed Insider Sale 2026-08-20

OSCR Form 144 filed for proposed insider sale by JEFFERY H. BOYD (288,514 shares) ~$9.56M

JEFFERY H. BOYD filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4. The proposed dollar value is large enough to merit attention.

Filing: Form 144 (Proposed Sale Notice) Insider: JEFFERY H. BOYD Shares: 288,514 Est. Value: $9.56M
View on SEC EDGAR → Open Filing Document →
Form 144 Proposed Insider Sale 2026-08-18

OSCR Form 144 filed for proposed insider sale by Richard Scott Blackley (18,750 shares) ~$614.2K

Richard Scott Blackley filed a Form 144 with the SEC indicating intent to sell OSCR (Oscar Health, Inc.) shares. Form 144 reflects a proposed sale, not a completed transaction. The actual execution, if any, would typically appear later in a Form 4.

Filing: Form 144 (Proposed Sale Notice) Insider: Richard Scott Blackley Shares: 18,750 Est. Value: $614.2K
View on SEC EDGAR → Open Filing Document →
Material Events 1 · Form 8-K

An 8-K reports a material event in the window between scheduled reports. There is 1 in this period for Oscar Health, Inc. Each 8-K names the item number it is filed under, and that number is the fastest way to tell a routine disclosure from a consequential one.

Item 2.02 is an earnings release, Item 5.02 is a change of directors or officers, and Item 1.01 or 2.01 covers a material agreement or a completed acquisition. Item 7.01 and Item 8.01 are the general-purpose disclosure items and carry no fixed meaning on their own.

Form 8-K Material Company Update 2026-09-16

OSCR filed 8-K — material company event

Oscar Health, Inc. filed an 8-K with the SEC reporting a material event. Summary unavailable — view the original SEC filing for the full text.

Filing: 8-K (Material Event)
View on SEC EDGAR → Open Filing Document →

How we classify Oscar Health, Inc.'s filings

Straight from EDGAR

Each displayed record links to an original source document. StrongBuyAnalytics provides navigation and brief excerpts or summaries, not the filing itself. Parsing may omit context or contain errors, so read the original document in full.

Transaction codes, not guesswork

The nature shown on each insider filing comes from the transaction code the filer entered on the form itself — P for an open-market purchase, A for a compensation award, F for shares withheld to pay tax, M for an option exercise. Where one filing contains several codes, the transaction table lists them line by line.

Why the distinction matters

Insider activity is routinely summarised as buying or selling, which flattens together decisions that mean very different things. Shares withheld for tax on a vesting grant are an automatic administrative step; shares bought on the open market are someone committing their own money at the current price.

What this page does not tell you

A filing records what happened, not why. Form 4 does not always disclose whether a sale was executed under a pre-arranged Rule 10b5-1 plan, and no single filing is a basis for a decision on OSCR. Read these alongside the fundamentals rather than in isolation.

Frequently Asked Questions — OSCR SEC Filings

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Publisher, sources & limitations — September 15, 2026. StrongBuyAnalytics provides navigation and brief excerpts or summaries for educational use. Original filings remain at SEC EDGAR or other displayed source links; StrongBuyAnalytics does not author them. Filing dates are source dates, not publication dates for this page. Coverage can be delayed, incomplete, amended, or unavailable because of SEC/source availability, parsing, caching, or outages. Verify every material statement in the original filing.
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