SKWD SEC Filing News — Skyward Specialty Insurance Group, Inc.

Latest SEC filings for Skyward Specialty Insurance Group, Inc. (SKWD) 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: 2026-08-20.

Skyward Specialty Insurance Group, Inc., an insurance holding company, provides commercial property and casualty insurance coverages in the United States. It offers general liability, excess liability, and professional liability, as well as cyber and media liability insurance; commercial auto, group accident and health, property, agriculture, credit, and surety and workers' compensation; and property, agriculture, and credit specialty reinsurance. The company was formerly known as Houston Intern…
Sector: Financial Services Industry: Insurance - Property & Casualty Market Cap: $2.7B
20
Total Filings
1
Bullish Classifications
2
Bearish Classifications
12
Insider Transactions
4
Material Events (8-K)
2
Periodic Reports
Rule-based classifications for SKWD currently lean bearish. Of the 20 filing records displayed, 2 carry bearish classifications (such as insider sales or negative 8-K disclosures) versus 1 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.
SKWD Filing Activity Snapshot 2026-05-08 — 2026-08-20
Insider Transactions (Form 4)
1 buy vs 2 sells
Net insider selling in this period — insiders sell for many reasons beyond conviction.
Largest Form 144 Filing
$431.0K
Schmitt Thomas N (CPO, Skyward Group) · 2026-06-15
8,397 shares · Form 4
Form 144 Notices
2
Proposed insider sales filed — Form 144 is a notice of intent, not a confirmed transaction. Actual sales are confirmed via Form 4.
Insider Transactions 12 · 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 12 filings in this group are Form 4s for Skyward Specialty Insurance Group, 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 12 insider filings shown, the breakdown is 7 option exercise, 2 compensation award, 2 open-market sale and 1 open-market purchase. 3 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.

What each transaction type means

Option exercise ×7
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Compensation award ×2
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Open-market sale ×2
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.
Open-market purchase ×1
The insider bought shares on the open market with their own money. This is the only Form 4 category that requires a discretionary cash outlay at the prevailing price.
Form 4 Compensation award Tax / Compensation Filing 2026-08-07

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

HEARN PETER C (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.

Transactions reported on this filing
Code Nature Shares Price Value
A Compensation award derivative · 2026 RSU Award 1,845 — —
Filing: Form 4 (Insider Transaction) Insider: HEARN PETER C (Director)
Form 4 Open-market sale Insider Selling 2026-06-15

SKWD insider Schmitt Thomas N (CPO, Skyward Group) sold 8,397 shares (~$431.0K)

Schmitt Thomas N, listed as CPO, Skyward Group at Skyward Specialty Insurance Group, Inc., reported an open-market sale of 8,397 SKWD 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 8,397 $51.32 $431.0K
Filing: Form 4 (Insider Transaction) Insider: Schmitt Thomas N (CPO, Skyward Group) Shares: 8,397 Est. Value: $431.0K
Form 4 Open-market purchase Insider Buying 2026-05-21

SKWD insider Kuczinski Anthony J (Director) bought 2,000 shares (~$94.2K)

Kuczinski Anthony J, listed as Director at Skyward Specialty Insurance Group, Inc., reported an open-market purchase of 2,000 SKWD shares in a Form 4 filing. Insider buying is often treated as a bullish signal because company insiders are committing their own capital.

The insider bought shares on the open market with their own money. This is the only Form 4 category that requires a discretionary cash outlay at the prevailing price.

Transactions reported on this filing
Code Nature Shares Price Value
P Open-market purchase 200 $47.00 $9.4K
P Open-market purchase 800 $47.00 $37.6K
P Open-market purchase 1,000 $47.20 $47.2K
Filing: Form 4 (Insider Transaction) Insider: Kuczinski Anthony J (Director) Shares: 2,000 Est. Value: $94.2K
Form 4 Open-market sale Insider Selling 2026-05-12

SKWD insider Ashe Gena L (Director) sold 740 shares (~$34.3K)

Ashe Gena L, listed as Director at Skyward Specialty Insurance Group, Inc., reported an open-market sale of 740 SKWD 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
M Option exercise 1,797 — —
S Open-market sale 100 $46.35 $4.6K
S Open-market sale 140 $46.35 $6.5K
S Open-market sale 500 $46.35 $23.2K
M Option exercise derivative · 2025 RSU Award 1,797 — —
Filing: Form 4 (Insider Transaction) Insider: Ashe Gena L (Director) Shares: 740 Est. Value: $34.3K
Form 4 Option exercise Tax / Compensation Filing 2026-05-08

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

Schmitt Thomas N (CPO, Skyward Group) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 3,358 — —
F Tax withholding on vested shares 1,322 $43.68 $57.7K
M Option exercise derivative · 2023 LTIP - PSUs 2,525 — —
Filing: Form 4 (Insider Transaction) Insider: Schmitt Thomas N (CPO, Skyward Group) Shares: 4,680
Form 4 Option exercise Tax / Compensation Filing 2026-05-08

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

Kapadia Sandip A (Head of Actuarial) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 2,686 — —
F Tax withholding on vested shares 1,374 $43.68 $60.0K
M Option exercise derivative · 2023 LTIP - PSUs 2,020 — —
Filing: Form 4 (Insider Transaction) Insider: Kapadia Sandip A (Head of Actuarial) Shares: 4,060
Form 4 Option exercise Tax / Compensation Filing 2026-05-08

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

Bodnar Dan PK (Chief Information Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 2,686 — —
F Tax withholding on vested shares 1,004 $43.68 $43.9K
M Option exercise derivative · 2023 LTIP - PSUs 2,020 — —
Filing: Form 4 (Insider Transaction) Insider: Bodnar Dan PK (Chief Information Officer) Shares: 3,690
Form 4 Option exercise Tax / Compensation Filing 2026-05-08

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

Burkhart John A III (President, US P&C) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 4,813 — —
F Tax withholding on vested shares 1,894 $43.68 $82.7K
M Option exercise derivative · 2023 LTIP - PSUs 3,619 — —
Filing: Form 4 (Insider Transaction) Insider: Burkhart John A III (President, US P&C) Shares: 6,707
Form 4 Option exercise Tax / Compensation Filing 2026-05-08

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

HAUSHILL MARK W (CFO - Skyward Group) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 5,036 — —
F Tax withholding on vested shares 1,982 $43.68 $86.6K
M Option exercise derivative · 2023 LTIP - PSUs 3,787 — —
Filing: Form 4 (Insider Transaction) Insider: HAUSHILL MARK W (CFO - Skyward Group) Shares: 7,018
Form 4 Option exercise Tax / Compensation Filing 2026-05-08

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

Robinson Andrew S (Director, Chairman & CEO, Skyward Group) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 20,150 — —
F Tax withholding on vested shares 7,930 $43.68 $346.4K
M Option exercise derivative · 2023 LTIP - PSUs 15,151 — —
Filing: Form 4 (Insider Transaction) Insider: Robinson Andrew S (Director, Chairman & CEO, Skyward Group) Shares: 28,080
Form 4 Option exercise Tax / Compensation Filing 2026-05-08

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

Duffy Sean W (EVP & Chief Claims Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.

Transactions reported on this filing
Code Nature Shares Price Value
M Option exercise 3,805 — —
F Tax withholding on vested shares 1,671 $43.68 $73.0K
M Option exercise derivative · 2023 LTIP - PSUs 2,861 — —
Filing: Form 4 (Insider Transaction) Insider: Duffy Sean W (EVP & Chief Claims Officer) Shares: 5,476
Form 4 Compensation award Tax / Compensation Filing 2026-05-08

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

Terry Katharine (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.

Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.

Transactions reported on this filing
Code Nature Shares Price Value
A Compensation award derivative · 2026 RSU Award 3,334 — —
Filing: Form 4 (Insider Transaction) Insider: Terry Katharine (Director)
Proposed Insider Sales 2 · 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. Skyward Specialty Insurance Group, Inc. has 2 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 2026-06-12

SKWD Form 144 filed for proposed insider sale by Thomas Schmitt (88 shares) ~$4.2K

Thomas Schmitt filed a Form 144 with the SEC indicating intent to sell SKWD (Skyward Specialty Insurance Group, 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: Thomas Schmitt Shares: 88 Est. Value: $4.2K
Form 144 Proposed Insider Sale 2026-05-11

SKWD Form 144 filed for proposed insider sale by Gena Ashe (740 shares) ~$34.3K

Gena Ashe filed a Form 144 with the SEC indicating intent to sell SKWD (Skyward Specialty Insurance Group, 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: Gena Ashe Shares: 740 Est. Value: $34.3K
Material Events 4 · Form 8-K

An 8-K reports a material event in the window between scheduled reports. There are 4 in this period for Skyward Specialty Insurance Group, 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 2026-08-20

SKWD filed 8-K — material company event

Skyward Specialty Insurance Group, 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)
Form 8-K Material Company Update 2026-08-04

SKWD filed 8-K — material company event

Skyward Specialty Insurance Group, 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)
Form 8-K Material Company Update 2026-07-15

SKWD filed 8-K — material company event

Skyward Specialty Insurance Group, 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)
Form 8-K Material Company Update 2026-05-11

SKWD filed 8-K — material company event

Skyward Specialty Insurance Group, 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)
Periodic Reports 2 · Forms 10-K and 10-Q

The periodic reports are where the audited and reviewed financial statements live. This period contains 2 quarterly reports (10-Q) for Skyward Specialty Insurance Group, Inc.

The two are not equivalent in weight. A 10-K is audited by an external firm and includes the full risk factor disclosure, business description and management discussion; a 10-Q is unaudited, reviewed rather than examined, and much shorter. When a figure in a quarterly report is later revised, the annual report is usually where the correction appears.

An amended report — 10-K/A or 10-Q/A — restates or corrects something in the original filing, and is worth reading against the version it replaces.

Form 10-Q Quarterly Report 2026-08-07

SKWD filed Quarterly Report (10-Q)

Skyward Specialty Insurance Group, Inc. filed its quarterly report with the SEC. This report includes unaudited financial statements and management discussion for the quarter.

Filing: 10-Q (Quarterly Report)
Form 10-Q Quarterly Report 2026-05-11

SKWD filed Quarterly Report (10-Q)

Skyward Specialty Insurance Group, Inc. filed its quarterly report with the SEC. This report includes unaudited financial statements and management discussion for the quarter.

Filing: 10-Q (Quarterly Report)

How we classify Skyward Specialty Insurance Group, 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 SKWD. Read these alongside the fundamentals rather than in isolation.

Frequently Asked Questions — SKWD 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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