Oscar Health (NYSE: $OSCR) Stock Hub 2026: A Record First Half, A Raised Guidance That Implies A Loss-Making Second Half, And An Investor Day On September 16
The largest half-year in the company’s history, $1,092.7 million of operating earnings against a full year range of $500 million to $700 million, membership down 211,487 in a quarter with another 250,000 to 300,000 retroactive disenrolments expected, and the first long-term targets due on September 16. What the filings say, every figure dated.
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Latest News
Primary-source check through September 3, 2026. No new SEC filing or company release has landed since the August 28 fiscal update beyond routine insider Form 4/144 activity; the two items below remain the operative news.
Oscar reports record first-half profitability and raises full-year 2026 guidance
CEO Mark Bertolini said Oscar delivered record profitability in the first half of the year. The raised guidance still implies an operating loss for the second half, as detailed in section 07 of this hub.
Oscar Health sets its 2026 Investor Day for September 16
Management will discuss corporate strategy, financial performance and long-term financial targets. As of this check, Oscar has published no 2027 guidance on revenue, membership, MLR or earnings.
Oscar files its second-quarter 10-Q, confirming the figures behind the raised guidance
The quarterly report backs the headline numbers in the August 6 release with the full financial statements and MD&A used throughout this hub.
Bull Case vs. Bear Case
The constructive case
First-half 2026 revenue reached $9,527.4 million with $1,092.7 million of earnings from operations and a 75.0% medical loss ratio — a record first half by the company’s own framing, on 2,963,002 effectuated members and $10.16 billion of cash and investments. Management raised full-year guidance off that base, and the September 16 Investor Day is the company’s first scheduled venue for long-term targets beyond 2026.
The sceptical case
The raised full-year guidance still implies a loss-making second half of roughly $(392.7) million to $(592.7) million, a reminder that individual-market insurance economics turn sharply in the back half of the year once risk adjustment and seasonal utilization catch up with first-half margins. No 2027 framework exists yet on revenue, membership, MLR or earnings; everything about the years after 2026 is an outside estimate until September 16.
Oscar announced on July 28, 2026 that it will host its 2026 Investor Day on Wednesday, September 16, 2026, beginning at 9:00 a.m. Eastern Time, with a live webcast on its investor relations site and an archive for about ninety days afterwards. Management said it will discuss corporate strategy, financial performance and long-term financial targets. As of September 3, 2026 the company has published no guidance for 2027 on revenue, membership, medical loss ratio or earnings, and the second half of 2026 is guided to an operating loss, so that morning is the first statement on the record about the period beyond this year.
At a glance
Oscar sells individual and family plans through the Affordable Care Act marketplaces in 20 states and no longer writes small group business. In 2025, 93 per cent of premiums were earned directly from the Centers for Medicare and Medicaid Services under the advanced premium tax credit programme and 7 per cent from members. In the first six months of 2026 risk adjustment transfers were approximately 20 per cent of direct policy premium revenue, four percentage points more than a year earlier, and the net risk adjustment payable stood at $4,846.1 million at June 30, 2026. That transfer is an estimate built on other insurers’ lagged data, finalised by CMS up to twelve months in arrears; the 2025 operating loss of $396.4 million came from this line moving the wrong way.
01 What Oscar Health Is In August 2026
Oscar Health, Inc. is a health insurer with a technology platform attached to it, and almost all of its revenue comes from one place: individual and family health plans sold through the marketplaces created by the Affordable Care Act. The company was founded in 2012, listed on the New York Stock Exchange in March 2021 under the ticker $OSCR, and is domiciled in Delaware with its head office at 75 Varick Street in New York.
The scale is no longer small. Oscar served approximately 3.0 million effectuated members at June 30, 2026, roughly 46 per cent more than a year earlier, and reported total revenue of $9,527.4 million in the first six months of 2026 against $5,910.2 million in the same period of 2025. For the 2025 policy year it offered coverage in 18 states; for 2026 it expanded to 20. It no longer sells small group plans, having ended that line on December 15, 2024, and it did not renew the Cigna+Oscar co-branded arrangement after its initial term expired on December 31, 2024.
Around the insurance carrier sit three wholly owned businesses that Oscar calls the Marketplace Subsidiaries: Lucie, Inc., formerly INSXCloud, an enrolment platform that is one of eleven CMS-approved solutions; Trove Group Inc., formerly IHC Specialty Benefits, an agency selling individual medical and supplemental products across carriers in all fifty states; and HealthInsurance.org, a lead-generation and education site. The +Oscar platform sells the company’s technology, including a campaign and engagement product, to other payors and providers.
Mark Bertolini, the former chief executive of Aetna, has run the company since 2023. Joshua Kushner, the co-founder, sits on the board through Thrive Capital. Mario Schlosser, the other co-founder, moved on June 1, 2026 from President of Technology and Chief Technology Officer to Co-Founder and Advisor to the chief executive, and remains a director.
02 The Individual Market After The Enhanced Subsidies Expired
One fact governs everything that follows: a subsidy that no longer exists. The enhanced Advanced Premium Tax Credits, which ran from 2021 until the end of 2025, made marketplace coverage materially cheaper for millions of people and pulled enrolment to record levels. They expired on December 31, 2025 and were not replaced.
Oscar’s own description, in the quarterly report filed on August 7, 2026, is direct: the expiry “caused coverage to become unaffordable for some individuals, reducing both the overall participation in the Health Insurance Marketplaces and the Company’s membership since the end of the 2026 open enrollment period”. The company adds that the expiry, combined with new program integrity requirements, “could continue to negatively impact the size of the Health Insurance Marketplaces and our membership in future years”, and that “any resulting market contraction could negatively impact market morbidity”.
The second half of that sentence matters more than the first. A smaller pool is not simply a smaller version of the same pool. People who drop coverage when the price rises are, on average, the ones who expect to use it least, which leaves a sicker average member behind. That is the mechanism behind the word morbidity, and it is the mechanism that produced Oscar’s 2025 loss.
Why 2025 and 2026 look like different companies. In 2025 Oscar priced for a market whose average risk turned out to be higher than assumed, and the correction ran through the risk adjustment accrual: the full year medical loss ratio was 87.4 per cent and the operating result was a loss of $396.4 million. For 2026 the company repriced. The first half medical loss ratio came in at 75.0 per cent. Neither number describes a steady state.
03 Membership: The 2026 Arc And The Retroactive Disenrolments
The membership series is the clearest single picture of what happened. Effectuated members were 1,676,970 at December 31, 2024 and 2,042,449 at December 31, 2025. After the 2026 open enrolment period they stood at 3,174,489 on March 31, 2026, a gain of more than a million in three months at a moment when the market as a whole was shrinking. Three months later, on June 30, 2026, they were 2,963,002.
That is a fall of 211,487 members, or 6.7 per cent, in a single quarter. And the decline did not stop at the quarter end. The 10-Q states that as of July 1, 2026 there were “approximately 250 thousand to 300 thousand members who we expect will be retroactively disenrolled in connection with CMS program integrity requirements or fraud, waste and abuse laws and regulations”.
Retroactive is the operative word. These are members whose premiums have in part already been recognised and whose claims have in part already been paid, and the amount Oscar expects to refund to CMS sits inside the payables to CMS line on the balance sheet. Two facts therefore hold at the same time: Oscar took share in a contracting market, and the share it took is being audited down.
A further 250,000 to 300,000 members were expected, as of July 1, 2026, to be retroactively disenrolled under CMS program integrity requirements.
Source: Quarterly results releases and Form 10-Q, June 30, 2026
04 The Second Quarter And The First Half In Numbers
The second quarter of 2026, reported on August 6, was the largest quarter in the company’s history on every operating line, and it followed a first quarter that was larger still on profitability.
| In thousands, except percentages | Q2 2026 | Q2 2025 | Six months 2026 | Six months 2025 |
|---|---|---|---|---|
| Total revenue | $4,880,220 | $2,863,945 | $9,527,414 | $5,910,208 |
| Premium revenue, net of risk adjustment | $4,789,331 | $2,803,444 | $9,370,193 | $5,799,265 |
| Medical expenses | $3,794,445 | $2,552,973 | $7,024,302 | $4,812,624 |
| Medical loss ratio | 79.2% | 91.1% | 75.0% | 83.0% |
| SG&A expense ratio | 14.2% | 18.7% | 14.7% | 17.2% |
| Earnings (loss) from operations | $388,635 | $(230,483) | $1,092,720 | $66,640 |
| Net income (loss) attributable to Oscar | $361,808 | $(228,361) | $1,040,804 | $46,910 |
| Diluted earnings per share | $1.10 | $(0.89) | $3.16 | $0.17 |
| Adjusted EBITDA | $415,349 | $(199,404) | $1,142,421 | $129,424 |
Two components of that improvement deserve to be separated from the rest. The second quarter medical loss ratio of 79.2 per cent included $164 million of favourable prior period reserve development, and the first quarter included a further $68 million. Prior period development is the correction of an earlier estimate: claims that were reserved for and did not arrive at the level assumed. It is real money and it is not repeatable by definition, because it comes from the conservatism of a previous quarter rather than from the economics of the current one.
The other component is the comparison base. The 91.1 per cent of the second quarter of 2025 carried the entire first-half 2025 risk adjustment true-up, which is why the year-on-year swing looks as violent as it does.
Six months ended June 30, 2026, total revenue of $9,527.4 million
- Medical expensesNet claims before ceded quota share reinsurance$7,024.3M73.7%
- Selling, general and administrative14.7% of total revenue, against 17.2% a year earlier$1,397.3M14.7%
- Depreciation and amortisation$13.1M0.1%
- Earnings from operations11.5% of total revenue$1,092.7M11.5%
Source: Oscar Health, second quarter 2026 results, August 6, 2026
05 The Medical Loss Ratio, Quarter By Quarter
Read as a series rather than as a pair of quarters, the ratio tells a plainer story: two bad years of pricing, a repricing for 2026, and a seasonal pattern that the company itself describes in detail.
Oscar’s own account of that seasonality is in the quarterly report. Members meet deductibles and out-of-pocket maximums over the course of the policy year, “which shifts more costs to us in the second half of the year as we pay a higher proportion of covered claims costs”. The company adds that the effect may be stronger in 2026 than usual, because newer members “tend to take time to engage with their benefits” and because “the shift to higher deductible plans could concentrate a higher portion of total costs to the second half of the year”.
A first-half ratio of 75.0 per cent against full year guidance of 81.5 to 82.5 per cent is therefore not a contradiction. It is the company saying that the second half will be considerably worse than the first, and saying so in the guidance rather than in a footnote.
Medical expenses as a percentage of net premiums before ceded quota share reinsurance. Full year 2026 guidance is 81.5% to 82.5%.
Source: Quarterly results releases, February 10 and November 6, 2025, May 6 and August 6, 2026
06 Risk Adjustment: The Largest Single Estimate In The Model
Risk adjustment is the mechanism by which plans with healthier than average members pay into a federal pool and plans with sicker than average members are paid out of it. For Oscar it is not a detail. In the first six months of 2026 risk adjustment transfers were approximately 20 per cent of direct policy premium revenue, four percentage points higher than in the same period of 2025.
| In thousands | Six months 2026 | Six months 2025 |
|---|---|---|
| Direct policy premiums | $11,696,744 | $6,832,435 |
| Risk adjustment transfers | $(2,314,281) | $(1,065,994) |
| Reinsurance premiums ceded | $(10,607) | $(5,232) |
| Assumed premiums | $(1,663) | $38,056 |
| Premium revenue as reported | $9,370,193 | $5,799,265 |
Nearly one dollar in five of the premium Oscar writes is handed to other insurers through this mechanism. The net risk adjustment payable stood at $4,846.1 million at June 30, 2026 against $2,559.6 million a year earlier.
The estimate is also the least certain number in the accounts, and the company says so. Risk scores are built on lagged claims data; the final reckoning from CMS arrives up to twelve months in arrears; the calculation depends on the risk profile of every other insurer in the same market, not only on Oscar’s own; and there is, in the company’s words, “additional uncertainty for both markets and blocks of business that experience outsized growth”. Oscar’s individual book grew by roughly half in a year. That is the definition of outsized growth, and 2025 is the demonstration of what happens when the estimate moves the wrong way.
07 The Guidance Raise Of August 6, And What Its Arithmetic Implies
On August 6, 2026 Oscar left its revenue range unchanged and raised everything below it.
| Full year 2026 outlook | February 10, 2026 | August 6, 2026 |
|---|---|---|
| Total revenue | $18.7bn to $19.0bn | $18.7bn to $19.0bn |
| Medical loss ratio | 82.4% to 83.4% | 81.5% to 82.5% |
| SG&A expense ratio | 15.8% to 16.3% | 15.6% to 16.1% |
| Earnings from operations | $250m to $450m | $500m to $700m |
The raise is large in percentage terms, and the subtraction underneath it is the part that moved the share price on the day. Earnings from operations in the first six months were $1,092.7 million. The top of the full year range is $700 million. Subtracting the half already reported from the year guided to leaves an implied second-half result of between a $392.7 million loss and a $592.7 million loss.
The same subtraction on revenue leaves $9,172.6 million to $9,472.6 million for the second half, against $9,527.4 million in the first, so the implied deterioration is a margin event rather than a volume event. Applying the guided full year medical loss ratio to a premium base that assumes investment and other income run at first-half rates gives an implied second-half ratio in the high eighties, in the region of 88 to 90 per cent. That last figure is an estimate built on a stated assumption, not a company disclosure; the two subtractions above are not.
What the guidance says in one line. Oscar has told the market that it expects to lose money from operations in the second half of 2026, on roughly the same revenue as the first half, and that the full year will still be its first profitable year since 2024. Both halves of that sentence come from the same table.
The first half is larger than the top of the full year range. The difference is the second half the company is guiding to.
Six months ended June 30, 2026
Raised on August 6, 2026 from $450 million
Raised on August 6, 2026 from $250 million
Loss from operations
Source: Oscar Health, second quarter 2026 results, August 6, 2026 and full year 2025 results, February 10, 2026
08 Where The Revenue Comes From, And Why The Cash Flow Looks Like That
Ninety-three per cent of the premiums Oscar earned in 2025 were paid directly by the Centers for Medicare and Medicaid Services under the advanced premium tax credit programme, and seven per cent by members. That is the concentration disclosed in the annual report, and it frames the business correctly: Oscar’s customer is the individual, but Oscar’s payer is the federal government.
The consequences run in both directions. On the favourable side, collection risk is minimal and the revenue line is administratively predictable. On the unfavourable side, every material variable in the model is set by rule rather than negotiated: who is eligible for a subsidy, how large it is, how long the enrolment window stays open, which verification documents an applicant must produce, and how much of a plan’s premium is transferred to a competitor through risk adjustment. A single change to the Notice of Benefit and Payment Parameters can move all of them.
The same dependency shows up in the cash flow statement. Net cash provided by operating activities was $4,711.3 million in the first half of 2026, against $1,387.6 million a year earlier. Of that, $3,365.2 million was the increase in payables to CMS and a further $443.1 million the increase in benefits payable. Operating cash flow of this shape is float, not earnings: it is money Oscar holds and will hand over later.
09 The Balance Sheet And The Payable Sitting Against The Cash
Total assets nearly doubled in six months, from $6,325.4 million at December 31, 2025 to $11,226.8 million at June 30, 2026. Cash and cash equivalents were $4,075.6 million, short-term investments $4,479.9 million and long-term investments $1,600.8 million.
Against that sits a liability that has grown faster than the assets. Payables to CMS were $6,095.3 million, up from $2,730.1 million at the end of 2025. That single line is larger than the cash balance, and it is the reason the balance sheet must be read as a whole rather than by its cash figure. Benefits payable, the reserve for claims incurred and not yet paid, was a further $1,898.4 million.
Total current liabilities were $8,689.5 million against total current assets of $9,373.2 million. Total stockholders’ equity was $2,055.2 million, against $980.7 million at the end of 2025, of which $2,052.0 million was attributable to Oscar Health, Inc. and $3.1 million to noncontrolling interests; the whole of that increase is the first-half profit, since the accumulated deficit fell from $3,294.4 million to $2,253.6 million. On the attributable figure, book value works out at roughly $6.65 per share on the 308.6 million Class A and Class B shares outstanding at June 30, 2026.
The cash is real and so is the payable sitting against it: $6.1 billion owed to CMS is the single largest line on the liability side.
Against $6,325.4 million at December 31, 2025
Risk adjustment and related items; up $3,365.2 million in six months
Of which $2,052.0M attributable to Oscar Health, Inc., or about $6.65 per share on the 308.6 million Class A and Class B shares outstanding
Two convertible issues; the revolving facility was undrawn
Source: Oscar Health Form 10-Q, June 30, 2026
10 Liquidity: $9.7 Billion In The Subsidiaries, $462.3 Million At The Parent
An insurance holding company does not have one cash balance, it has two, and the difference between them is regulatory rather than accounting.
At June 30, 2026 the Health Insurance Subsidiaries held $9.7 billion of cash and investments, of which $19.6 million was on deposit with regulators for statutory licensing. The parent company and the subsidiaries that are not insurers held $462.3 million, of which $9.6 million was restricted. At December 31, 2025 the two figures were $5.1 billion and $414.2 million.
Money inside a regulated insurer belongs, in practice, to the policyholders and the state insurance departments until a dividend is approved. The company lists among its risk factors the ability of those subsidiaries “to make payments of dividends or distributions to us, including to fund our business strategy”. So the $9.7 billion is a solvency number and the $462.3 million is the corporate one: it is what services the convertible coupons, funds acquisitions and absorbs head-office costs without asking a regulator first.
Behind it stands a facility signed on February 6, 2026: a $475.0 million secured three-year revolving credit line arranged by JPMorgan Chase, expiring on February 6, 2029, with an accordion of a further $100.0 million. Borrowings would price at term SOFR plus 4.50 per cent or the alternate base rate plus 3.50 per cent, and the undrawn commitment fee started at 0.50 per cent. Nothing was drawn at June 30, 2026. The pricing is not investment-grade pricing, which is itself information about how the lending market reads the credit.
At June 30, 2026. A year-end 2025 the two figures were $5.1 billion and $414.2 million.
- Health Insurance Subsidiaries$9.7B · 95.5%Of which $19.6 million on deposit with regulators; distributions to the parent require regulatory clearance
- Parent and non-insurance subsidiaries$462.3M · 4.5%Of which $9.6 million restricted; this is the money that services the converts and funds corporate strategy
Source: Oscar Health Form 10-Q, June 30, 2026
11 Capital Structure: Two Convertible Issues And The Dilution Already Reported
Long-term debt was $431.6 million at June 30, 2026, and all of it is convertible.
- 2030 Notes. $410.0 million issued on September 18, 2025, 2.25 per cent coupon payable semi-annually, maturing September 1, 2030, convertible at approximately $24.82 per Class A share on an initial rate of 40.2946 shares per $1,000 of principal.
- 2031 Notes. $305.0 million originally issued in February 2022 to funds affiliated with Dragoneer, Thrive Capital, LionTree and Tenere at a 7.25 per cent coupon, maturing December 31, 2031, convertible at approximately $8.32 per share on a rate of 120.1721 shares per $1,000. After the exchange transactions of November 2025, $35 million of principal remained outstanding at June 30, 2026.
Both are in the money. The 10-Q states that during the quarter ended June 30, 2026 the share price condition on the 2031 Notes was satisfied, because the stock traded above 130 per cent of the $8.32 conversion price for at least twenty of the last thirty trading days of the quarter, so holders may elect to convert during the third quarter of 2026.
The dilution is already visible in the reported numbers rather than hiding behind them. Class A and Class B shares outstanding were 308.6 million at June 30, 2026, while the diluted weighted average share count used for the quarter was 333.4 million. Full conversion of both issues alone would add roughly 20.7 million shares on the stated conversion rates. That gap is why diluted earnings per share of $1.10 sits well below basic earnings per share of $1.20 for the same quarter.
12 The 2027 Rulebook: Columbus I, Columbus II And The Payment Parameters
The rules that will govern the 2027 plan year have been written, challenged in court, partly struck down, rewritten and partly stayed again, all within about twelve months. The sequence matters because Oscar has to price 2027 plans against whichever version survives.
- July 4, 2025. The One Big Beautiful Bill Act is signed into law, adding verification procedures for eligibility for advanced premium tax credits and limiting eligibility for certain populations.
- June 25, 2025. CMS issues the Program Integrity Rules: stricter eligibility verification, shorter open enrolment periods, suspension of certain special enrolment periods.
- August 22, 2025. In City of Columbus vs. Kennedy, a federal district court in Maryland issues a nationwide stay on several of those provisions. They were not in effect during the 2026 open enrolment period. The provisions untouched by the stay took effect on August 25, 2025.
- June 12, 2026. The court issues a final ruling nullifying the stayed provisions and certain others.
- May 15, 2026. The Department of Health and Human Services finalises the Notice of Benefit and Payment Parameters for plan year 2027, reintroducing updated versions of several nullified provisions, including income verification requirements where data indicates household income below the federal poverty line, and a rule making a tax filer ineligible for credits if they failed to file a return reconciling an earlier year’s credits.
- June 3, 2026. Plaintiffs challenge the 2027 rules in a second case, referred to in the filings as Columbus II.
- July 16, 2026. The court issues a nationwide stay on several provisions of the 2027 parameters, including the income verification rules and the one-year failure-to-reconcile rule, pending a ruling on the merits. Provisions unaffected by the stay took effect on July 20, 2026.
Two practical consequences follow for the coming enrolment season. The 2027 open enrolment period reverts to the historical November 1 to January 15 window, which is longer than the shortened one CMS had sought. And if the stayed provisions are eventually implemented, Oscar expects them to affect subsidy eligibility and enrolment processes beginning with that same 2027 season. The direction of the next enrolment cycle depends on a court docket.
13 Tariffs On Patented Pharmaceuticals And The Rebate Channel
A second regulatory thread runs through the drug supply chain rather than the insurance rules. On April 2, 2026 a proclamation under Section 232 of the Trade Expansion Act imposed 100 per cent tariffs on patented pharmaceuticals and associated ingredients imported into the United States, effective July 31, 2026 for certain named companies and September 29, 2026 for everyone else, unless manufacturers agree to specific government drug pricing deals or commit to shifting production and research onshore.
Oscar’s exposure is indirect and asymmetric. The company explains that pressure on list prices could bring “a corresponding, or even disproportionate, decrease in the pharmaceutical rebates that we negotiate and typically receive”, and that because those rebates are built into premium pricing, “a reduction in rebates that outpaces any decline in underlying drug costs could exert financial pressure, potentially leading to an adverse impact on our earnings from operations and an increase in our MLR”. Beyond rebates, the company lists higher provider and device costs and possible shortages of medicines as further channels.
The September 29, 2026 date falls inside the second half that guidance already describes as loss-making, and inside the pricing work for the 2027 plan year.
14 September 16, 2026: The Investor Day And The Long-Term Targets
The nearest scheduled company event is an Investor Day. Oscar announced on July 28, 2026 that it will host its 2026 Investor Day on Wednesday, September 16, 2026, beginning at 9:00 a.m. Eastern Time, with a live webcast on its investor relations site and an archive available for about ninety days afterwards.
The announced agenda is the reason the date carries weight: management “will discuss the Company’s corporate strategy, financial performance, and long-term financial targets”. Long-term financial targets is the specific phrase. Oscar has not published a 2027 outlook, and the second half of 2026 is guided to an operating loss, so the first framework the company offers for the years beyond this one is scheduled for that morning.
What is not yet on the record. As of August 28, 2026 there is no company guidance for 2027 revenue, membership, medical loss ratio or earnings, and no disclosed 2027 rate filing position, in any filing or release reviewed for this hub. Anything circulating about 2027 margins before September 16 is an outside estimate.
15 The Businesses Around The Insurer: Lucie, Trove And The ICHRA Bet
The businesses around the carrier are small in revenue and large in strategic intent. Oscar acquired them in 2025 and groups them as the Marketplace Subsidiaries.
- Lucie, Inc., formerly INSXCloud, a direct enrolment technology platform and one of only eleven CMS-approved solutions, which is a licence competitors cannot simply buy.
- Trove Group Inc., formerly IHC Specialty Benefits, an agency distributing individual medical and supplemental products from multiple carriers in all fifty states.
- HealthInsurance.org, an education and lead generation site covering the marketplaces, Medicare and Medicaid.
The thesis behind them is the Individual Coverage Health Reimbursement Arrangement, or ICHRA, the mechanism by which an employer funds an account and the employee buys an individual plan instead of being enrolled in a group plan. Oscar counts ICHRA members inside its individual membership and has built distribution, enrolment technology and a supplemental product shelf around the idea that employer-sponsored coverage will keep migrating toward the individual market.
Bertolini put the demographic case in the second-quarter release: “More people are moving between full- and part-time jobs, gig work, and retirement – a shift AI will accelerate. A durable individual market gives them greater choice and will power the future of American healthcare.” Whether that migration happens at the pace the company assumes is the central open question of the equity story, and it is not one that any quarter settles.
16 Management, The Dual Class Structure And The Controlled Company Status
Oscar has a dual class structure. Class A shares carry one vote; Class B shares carry twenty. At the record date for the 2026 annual meeting there were 265,530,268 Class A shares and 35,591,356 Class B shares outstanding, which means the Class B holders controlled roughly 711.8 million of the approximately 977.4 million votes available, or about 73 per cent, while holding around 12 per cent of the equity. The company identifies itself as a controlled company and lists the associated adverse consequences among its risk factors.
At the annual meeting held on June 4, 2026 all eight director nominees were elected, executive compensation was approved on an advisory basis and PricewaterhouseCoopers was ratified as auditor. Broker non-votes ran to 45,930,469 on the first two proposals. The board comprises Mark Bertolini, William J. Gassen III, Joshua Kushner, Laura Lang, David Alexander Plouffe, Siddhartha Sankaran, Mario Schlosser and Vanessa Ames Wittman.
The main governance change of the year was Schlosser’s move on June 1, 2026 from President of Technology and Chief Technology Officer to Co-Founder and Advisor to the chief executive. Under the amended agreement his base salary is $370,000, he is no longer eligible for an annual bonus from 2026, he will receive no new long-term or equity awards, and he is entitled to no cash severance on any termination. He continues to vest in awards already granted and remains on the board.
17 What The Insiders Have Been Doing Since June
Between June 23 and August 27, 2026 the two largest individual holders inside the company sold or registered to sell a substantial number of shares. The filings are public and the mechanics matter as much as the totals.
| Filing | Person | Dates | Shares | Prices | Holding after |
|---|---|---|---|---|---|
| Form 4 filed June 29, 2026 | Mark T. Bertolini, chief executive | June 25 and 26, 2026 | 1,206,310 sold | $28.60 to $29.79 weighted average | 8,990,566 |
| Form 4 filed July 1, 2026 | Mark T. Bertolini, chief executive | June 29 and 30, 2026 | 1,238,996 sold | $28.35 to $30.08 weighted average | 7,751,570 |
| Form 4 filed June 25, 2026 | Mario Schlosser, co-founder and director | June 23, 2026 | 1,027,500 sold after option and unit conversions | $28.95 to $30.09 weighted average | Blocks taken to zero |
| Form 4 filed July 6, 2026 | Mario Schlosser, co-founder and director | July 1, 2026 | 47,500 sold after conversion | $29.50 to $31.65 | Block taken to zero |
| Form 4 filed August 20, 2026 | R. Scott Blackley, chief financial officer | August 18, 2026 | 18,750 sold | $31.74 weighted average, range $31.28 to $32.15 | 56,250 |
| Form 144 filed August 27, 2026 | Mario Schlosser, co-founder and director | Proposed August 27, 2026 | 600,000 from a stock option exercise | $18,205,505.85 aggregate market value | Notice of proposed sale |
The chief executive’s two Form 4s cover 2,445,306 shares over four trading sessions, roughly $70.7 million at the weighted average prices reported, and both carry the Rule 10b5-1 flag. A footnote attributes part of the June 29 and 30 sales to shares sold to cover tax withholding on performance stock units that vested on April 3, 2026, under an instruction letter entered into on November 10, 2025 and amended on March 24, 2026. Schlosser’s June sales were made under a Rule 10b5-1 plan adopted on March 24, 2026. The two filings that cover his June 23 disposals do not agree to the share: the transaction lines of the Form 4 add up to 1,027,500 shares, while the Form 144 of August 27 reports 1,027,398 shares sold on that date for gross proceeds of $30,183,414. That same Form 144 also discloses 34,120 shares sold on June 2 for $748,633.08.
The chief financial officer’s Form 4 of August 20 is the one filing in the set where the Rule 10b5-1 box is not checked. It covers 18,750 shares, a small transaction beside the others, and after it he held 56,250 shares including units still to be issued.
Board grants ran the other way and are routine: five directors each received 8,475 shares on June 4, 2026, the day of the annual meeting.
18 Market Data And Sell-Side Coverage
| Market data | Reading |
|---|---|
| Market capitalisation | Approximately $9.27 billion, on 308.6 million Class A and Class B shares outstanding at June 30, 2026 (Merlintrader calculation) |
| Float and insider ownership | 251.35 million shares of float, insider ownership 18.58% |
| Short interest | 6.54% of float, 2.71 days to cover |
| Trailing and forward price to earnings | 22.58 and 16.24 |
| Price to book | Approximately 4.5 times the $6.65 of book value per share at June 30, 2026 |
| Sell-side consensus target | $30.82, Finviz aggregate |
| Sell-side consensus rating | 2.58 on the Finviz one-to-five scale, where one is the most positive |
Market and consensus readings were taken from Finviz Elite on September 3, 2026 and change continuously. The sell-side consensus target of $30.82 sits close to the multiples discussion below: the valuation implied by that target still has to be reconciled with a second half guided to an operating loss.
The valuation multiples carry their own warning label. A trailing price to earnings of 22.58 is calculated on twelve months that contain two exceptional quarters and two loss-making ones, and the company’s own guidance implies the next two quarters will be loss-making at the operating line. A multiple built on that base is arithmetic, not a description of run-rate earnings.
19 Retail Sentiment On Stocktwits
Retail sentiment is a picture of what non-professional traders are saying, not of what analysts or the company think, and it is quoted here on that basis.
On Stocktwits, on August 28, 2026, tagged messages on the $OSCR stream ran 84.62 per cent bullish against 15.38 per cent bearish, while the platform’s own composite reading for the symbol was 35 out of 100, carrying a bearish label. The two figures disagree because they measure different things: the percentages count only messages a poster chose to tag, the composite blends message flow and other activity.
The recurring themes in the stream over the last week of August were narrow. Traders were watching a range between roughly $30 and $32 and treating the September Investor Day as the event that breaks it, with one post summarising the mood as expecting the stock to sit “between 30 and 32 until investor day”. A second theme was the read-across from other healthcare names, with $CNC and $HIMS mentioned repeatedly as comparables trading on the same policy news. A third, smaller strand was frustration at low-volume drift after the August 24 high.
None of this is analysis. It is a measure of attention, and attention on this name is currently pointed at one date.
20 The Catalyst Map
| When | What | Status |
|---|---|---|
| September 16, 2026 | 2026 Investor Day, 9:00 a.m. Eastern Time, webcast: corporate strategy, financial performance and long-term financial targets | Confirmed by the company on July 28, 2026 |
| September 29, 2026 | Section 232 tariffs of 100% on patented pharmaceuticals take effect for companies not named in the earlier tranche | Date set by the April 2, 2026 proclamation |
| Third quarter 2026 | Holders of the remaining $35 million of 2031 Notes may elect to convert, the share price condition having been met | Disclosed in the 10-Q |
| Autumn 2026 | State approval and publication of 2027 individual market rates, and Oscar’s decisions on which of its 20 states to keep | Process, no company date |
| Early November 2026 | Third quarter 2026 results, the first quarter to test the loss-making second half implied by guidance | Not yet announced as of August 28, 2026 |
| November 1, 2026 to January 15, 2027 | 2027 open enrolment period, reverted to the historical window after the June 12, 2026 ruling | Window set by rule |
| No date | Ruling on the merits in Columbus II, which decides whether the stayed 2027 provisions apply | Pending, stay issued July 16, 2026 |
| No date | Any congressional action on the expired enhanced premium tax credits, or funding of a cost-sharing reduction programme | Listed by the company as a forward-looking risk factor, no legislation enacted as of August 28, 2026 |
The distribution of that list is itself informative. One catalyst has a confirmed date and a disclosed agenda; the rest are either mechanical, or set by a court and a legislature that have moved four times in twelve months.
21 Risks And Red Flags
- The second half is guided to a loss. Subtracting first-half earnings from operations of $1,092.7 million from the full year range of $500 million to $700 million leaves an implied second-half operating loss of $392.7 million to $592.7 million.
- Reserve development flattered the first half. $164 million of favourable prior period development in the second quarter and $68 million in the first are corrections of earlier estimates, not recurring margin.
- Membership is being audited down. Members fell 211,487 between March 31 and June 30, 2026, and a further 250,000 to 300,000 were expected as of July 1 to be retroactively disenrolled under program integrity requirements.
- Risk adjustment is one fifth of premium and is an estimate. Transfers were about 20 per cent of direct policy premium in the first half, the net payable was $4,846.1 million at June 30, and the calculation depends on other insurers’ data that arrives up to twelve months in arrears. The 2025 loss came from exactly this line.
- One product, one market, one payer. Ninety-three per cent of 2025 premiums were paid directly by CMS. There is no diversified segment to absorb a bad policy year.
- The rulebook for 2027 is unsettled. Two rounds of litigation, a nullification and a nationwide stay have all landed within twelve months, and the pricing for the next enrolment season has to be set against whichever version survives.
- Cash is not free cash. Of the $4,711.3 million of first-half operating cash flow, $3,365.2 million was the increase in payables to CMS. The parent company held $462.3 million, against $9.7 billion inside regulated subsidiaries that need approval to distribute it.
- Dilution is live. The diluted share count of 333.4 million sits 24.8 million above the 308.6 million shares outstanding, and holders of the 2031 Notes may convert during the third quarter of 2026.
- Insider selling has been heavy. The chief executive sold 2,445,306 shares over four sessions in late June under a Rule 10b5-1 plan, and the co-founder filed on August 27 to sell a further 600,000.
- The stock has already moved. Up roughly 109 per cent year to date and approximately 180 per cent from the March low, against a consensus target essentially level with the last close.
22 Scenarios
These are descriptions of paths the disclosed facts leave open, not forecasts and not advice. Each one is defined by what would have to be true, so that a reader can check it against the next set of numbers rather than against an opinion.
The case the bulls are making. Oscar reprices a market that its competitors have partly abandoned, keeps a disciplined loss ratio through a heavier second half, hits or beats the raised $500 million to $700 million operating range, and uses the September 16 Investor Day to put multi-year targets on the individual market and the ICHRA migration. In that path the second half loss is seasonal rather than structural, the 2027 enrolment window is longer than CMS had wanted, and the company enters 2027 with 20 states, a repriced book and $9.7 billion of subsidiary capital.
The case the bears are making. The first half was flattered by $232 million of favourable development and by a comparison base distorted by the 2025 true-up; membership is falling and being disenrolled retroactively; the market keeps contracting while its average member gets sicker; and the guided second-half loss turns out to be the start of a trend rather than a seasonal dip. In that path the 2027 pricing round has to be made against an unsettled rulebook and a smaller pool, and the risk adjustment estimate moves the wrong way again, as it did in 2025.
What separates the two is measurable and dated. The third quarter report, due in early November, is the first observation of the guided second half. The Investor Day of September 16 is the first statement of what management thinks the years after 2026 look like. A ruling in Columbus II decides which set of eligibility rules applies to the enrolment season that opens on November 1.
23 Bottom Line
Oscar Health in August 2026 is a company whose reported numbers and whose own guidance point in opposite directions over the next six months, and both come from the same press release.
The reported half is the best in the company’s history: $9,527.4 million of revenue, a 75.0 per cent medical loss ratio, $1,092.7 million of operating earnings and $3.16 of diluted earnings per share, against a full year 2025 that lost $396.4 million at the operating line. The guided half is an operating loss of roughly $390 million to $590 million on similar revenue, driven by the seasonality the company describes in its own filing and by a market that shrank when the enhanced subsidies expired.
Everything else follows from how those two halves are weighted. The balance sheet is larger but so is what it owes: $6,095.3 million of payables to CMS against $4,075.6 million of cash, and $462.3 million of that liquidity actually at the parent. The share price has already discounted a recovery, trading up 109 per cent year to date against a consensus target of $30.82. The insiders who know the model best sold heavily in June and filed to sell more in August, under plans adopted in advance.
The next fixed point on the calendar is September 16, 2026, when management has said it will present long-term financial targets. Until then there is no company statement about 2027 at all.
Related Research On Merlintrader
- Biotech and healthcare stock hubs: the full index, with the update date of every hub.
- Hims & Hers Health ($HIMS) stock hub, the other consumer-facing healthcare name covered here.
- Free Biotech Catalyst Calendar, with confirmed regulatory and clinical dates.
- Weekly Market Pulse, the week’s verified earnings and catalyst calendar.
Primary Sources And Reference Links
- Oscar Health, second quarter 2026 results, Form 8-K exhibit 99.1, August 6, 2026: quarterly and half-year figures, membership, updated 2026 guidance.
- Form 10-Q for the quarter ended June 30, 2026, filed August 7, 2026: balance sheet, liquidity by level, debt, risk adjustment, regulatory update, retroactive disenrolments, tariffs.
- First quarter 2026 results, Form 8-K exhibit 99.1, May 6, 2026: March 31 membership, first quarter ratios, reaffirmed guidance.
- Fourth quarter and full year 2025 results, Form 8-K exhibit 99.1, February 10, 2026: 2025 outturn and the original 2026 outlook.
- Third quarter 2025 results, Form 8-K exhibit 99.1, November 6, 2025: the third quarter 2025 loss ratio used in the series above.
- Annual Report on Form 10-K for 2025, filed February 13, 2026: states served, premium concentration, the Marketplace Subsidiaries, risk factors.
- Oscar Health, Inc. to Host 2026 Investor Day, Business Wire, July 28, 2026: the September 16, 2026 date, time and agenda.
- Form 8-K of June 9, 2026: annual meeting results and the share counts by class at the April 10, 2026 record date.
- Form 8-K of June 2, 2026: the amended employment agreement for Mario Schlosser.
- Forms 4 and 144 filed for Oscar Health: the insider transactions of June, July and August 2026 quoted above.
- Prices, float, short interest, consensus target and consensus rating: Finviz Elite, reading of August 28, 2026. Retail sentiment: Stocktwits public data for $OSCR, same date.
Every figure above comes from the filings and releases listed here, with its reference date stated in the text. Market and sentiment readings were taken on August 28, 2026 and change continuously.
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Disclaimer. This content is published by Merlintrader for educational and informational purposes only. It is independent journalism and research. It does not constitute investment advice, an investment recommendation, an offer or a solicitation to buy or sell any security, and it is not a research report within the meaning of applicable United States securities regulation. Nothing here should be read as a recommendation to buy, sell or hold $OSCR or any other security.
Figures are taken from public filings with the U.S. Securities and Exchange Commission, company press releases and market-data providers, and are stated with their reference dates. Data can change without notice, and figures published before a results release become outdated the moment that release is issued. Merlintrader makes no representation that the information is complete or current at the time of reading. Readers should verify every figure against the primary source before acting on it.
Oscar Health earns almost all of its revenue from one regulated market whose rules, subsidies and eligibility requirements have changed four times in twelve months and are currently subject to litigation. Its own guidance implies an operating loss in the second half of 2026, and its risk adjustment estimate is finalised by a third party up to twelve months in arrears. Securities of companies in this position can lose a large part of their value.
Merlintrader may hold positions in securities mentioned. Some links on this page are affiliate or referral links, including those to Finviz and Stocktwits, which may generate a commission at no cost to the reader. Full legal information is available on the disclaimer and terms of use and privacy pages.
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