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                              May 19, 2022

       Andrew Robinson
       Chief Executive Officer
       Skyward Specialty Insurance Group, Inc.
       800 Gessner Road, Suite 600
       Houston, TX 77024

                                                        Re: Skyward Specialty
Insurance Group, Inc.
                                                            Draft Registration
Statement on Form S-1
                                                            CIK No. 0001519449
                                                            Submitted April 22,
2022

       Dear Mr. Robinson:

              We have reviewed your draft registration statement and have the
following comments. In
       some of our comments, we may ask you to provide us with information so
we may better
       understand your disclosure.

              Please respond to this letter by providing the requested
information and either submitting
       an amended draft registration statement or publicly filing your
registration statement on
       EDGAR. If you do not believe our comments apply to your facts and
circumstances or do not
       believe an amendment is appropriate, please tell us why in your
response.

             After reviewing the information you provide in response to these
comments and your
       amended draft registration statement or filed registration statement, we
may have additional
       comments.

       Draft Registration Statement on Form S-1

       General

   1.                                                   Please provide us with
supplemental copies of all written communications, as defined in
                                                        Rule 405 under the
Securities Act, that you, or anyone authorized to do so on your behalf,
                                                        have presented or
expect to present to potential investors in reliance on Section 5(d) of the
                                                        Securities Act, whether
or not you retained, or intend to retain, copies of those
                                                        communications. Please
contact Tonya K. Aldave at (202) 551-3601 to discuss how to
                                                        submit the materials,
if any, to us for our review.
       Market, Industry and Other Data, page ii

   2.                                                   We note you indicate
that the prospectus includes market and industry data from industry
 Andrew Robinson
FirstName  LastNameAndrew   Robinson
Skyward Specialty Insurance Group, Inc.
Comapany
May        NameSkyward Specialty Insurance Group, Inc.
     19, 2022
May 19,
Page 2 2022 Page 2
FirstName LastName
         publications and that those sources generally state that the
information they provide has
         been obtained from sources believed to be reliable, but that the
accuracy and completeness
         of the information are not guaranteed. Please revise to clarify that,
notwithstanding the
         foregoing, you believe that this information is reliable.
Prospectus Summary, page 1

3.       We note your disclosure on page 6 that as of December 31, 2021, "95.7%
of
         [your] reinsurance recoverables were either derived from reinsurers
rated    A-    (Excellent)
         by A.M. Best, or better." Please revise for consistency with your
disclosure in the table on
         page 97 where you state that $116,822,000 in reinsurance recoverables,
or approximately
         21.8% of the total $536,327,000 in reinsurance recoverables, was
attributed to Randall
         & Quilter and eCaptive PC1-IC, two reinsurers that are "unrated" by
the AMB Best
         Ratings.
Use of Proceeds, page 44

4.       Please state the approximate amount intended to be used for each
purpose listed in the
         second sentence of the third paragraph, or tell us why you are unable
to do so.
Management's Discussion and Analysis of Financial Condition
Loss Portfolio Transfer, page 50

5.       Please disclose the identity of "a third party reinsurer" referenced
in the first sentence of
         this section.
Reconciliation of Non-GAAP Financial Measures, page 58

6.       Please tell us why it is appropriate to exclude the entire impact of
your loss portfolio
         transfer (LPT) in your non-GAAP measures when you disclose on page 50
and elsewhere
         that the LPT relates to business that has been predominantly exited.
For the portions of the
         business not exited, it appears that the removal of the LPT impacts
results in the removal
         of normal, recurring, cash operating expenses of your business. See
Question 100.01 of
         the Compliance and Disclosure Interpretations on Non-GAAP Financial
Measures. In
         your response, specifically tell us how your adjusted loss ratio
presented on page 56 is
         meaningful if the entire net impact of the LPT is removed when
presumably the net earned
         premiums on business not "predominantly exited" are included in the
denominator of the
         ratio.
7.       Please revise your reconciliations of Adjusted operating income and
Underwriting income
         to describe and quantify the components of the "Other income and
(expenses)"
         adjustment.
Credit Agreements, page 62

8.       Please disclose your counterparties for the "Revolver" and the "Term
Loan" described on
         pages 62 and 63 of the prospectus. In addition, tell us if you have
filed these agreements
 Andrew Robinson
FirstName  LastNameAndrew   Robinson
Skyward Specialty Insurance Group, Inc.
Comapany
May        NameSkyward Specialty Insurance Group, Inc.
     19, 2022
May 19,
Page 3 2022 Page 3
FirstName LastName
         and described their material terms.
Industry
Cyclicality of the Industry, page 78

9.       We note your discussion about the cyclicality of the insurance
industry. Please specify the
         current state of the insurance industry and, if necessary, add
tailored risk factor
         disclosure. In that regard, please clarify in the risk factor heading,
"[t]he insurance
         business is historically cyclical in nature," where the industry is in
the cycle, so that
         investors may assess the risk.
Business
Reinsurance, page 95

10.      Please refer to the table on page 97 and disclose the percentage of
coverage ceded to each
         reinsurer and the nature and amount of collateral in trust under the
contracts.
Reserves, page 98

11.      Please tell us why development related to accident years 2019 and 2020
(and presumably
         2018 included in the "Prior" accident year totals) is characterized as
relating to the LPT
         when the LPT relates to policies years 2017 and prior. To the extent
that this development
         relates to exited lines, revise your disclosure to clarify and explain
why you continue to
         incur losses on exited lines.
Loss Portfolio Transfer, page 99

12.      Please disclose the "third party reinsurer domiciled in Bermuda"
referenced in the first
         sentence of this section or advise. In addition, if this is a material
agreement not made in
         the ordinary course of business, file it as an exhibit to the
registration statement or advise
         why you are not required to do so.
Executive Compensation, page 122

13.      Please advise why you have not also included a separate table for the
non-equity incentive
         plan compensation, which is included as a separate column in your
summary
         compensation table. Refer to Item 402(d) of Regulation S-K.
Employee Benefit and Equity Incentive Plans, page 126

14.      Once you have an estimated offering price or range, please explain to
us how
         you determined the fair value of the common stock underlying your
equity issuances and
         the reasons for any differences between the recent valuations of your
common
         stock leading up to the IPO and the estimated offering price. This
information will help
         facilitate our review of your accounting for equity issuances
including equity
         compensation.
 Andrew Robinson
FirstName  LastNameAndrew   Robinson
Skyward Specialty Insurance Group, Inc.
Comapany
May        NameSkyward Specialty Insurance Group, Inc.
     19, 2022
May 19,
Page 4 2022 Page 4
FirstName LastName
Principal and Selling Stockholders, page 136

15.      Please identify the natural persons who have voting or dispositive
power with respect to
         the shares of the entities listed under 5% and Greater Shareholders.
Exclusive Forum, page 141

16.      We note the disclosure here that the federal district court will be
the exclusive forum for
         the resolutions of any complaint asserting a cause of action arising
under the Securities
         Act. Your risk factor disclosure on page 40 under "[o]ur certificate
of incorporation and
         bylaws," seems to indicate that the discussed exclusive forum
provision for disputes in the
         Court of Chancery of the State of Delaware applies to Securities Act
claims. Please revise
         for consistency or advise.
Notes to Consolidated Financial Statements
2. Summary of Significant Accounting Policies
Stock Based Compensation, page F-17

17.      If true, please revise your policy disclosure to highlight that
compensation for awards with
         market conditions is not reversed if the service was delivered but the
market condition not
         attained consistent with the guidance in ASC 718-10-30-14 while any
compensation for
         awards with a performance conditions would be reversed if the
performance condition
         ultimately is not achieved consistent with the guidance in ASC
718-10-30-12. If your
         policy does not conform with the referenced guidance, tell us the
impact of applying it.
4. Goodwill and Intangible Assets, page F-20

18.      Revise to disclose the facts and circumstances leading to the
impairment of goodwill
         during 2021 and 2020, and the method of determining fair value for the
reporting unit
         used in the impairment caluclations. Refer to ASC 350-20-50-2.
5. Investments, page F-23

19.      Please tell us why the amortized cost and fair value of your held to
maturity asset-backed
         securities are the same at both December 31, 2021 and 2020. In your
response, tell us:
             when you acquired these securities; and
             the market rate of interest for these securities at:
                o  acquisition;
                o  December 31, 2020; and
                o  December 31, 2021

20.      On page F-26 you disclose that the proceeds from the sales of your
held to maturity fixed
         maturity securities were approximately $0.0 million in 2021 and $7.7
million in 2020.
         Please tell us whether you actually sold these securities or whether
the proceeds are the
         result of maturities or prepayment on the loans underlying your
asset-backed securities. If
         you sold any held to maturity securities, provide us your analysis as
to how these sales do
 Andrew Robinson
FirstName  LastNameAndrew   Robinson
Skyward Specialty Insurance Group, Inc.
Comapany
May        NameSkyward Specialty Insurance Group, Inc.
     19, 2022
May 19,
Page 5 2022 Page 5
FirstName LastName
         not taint held to maturity classification for your remaining
investments as stipulated in
         ASC 320-10-35-8 and 35-9.
6. Fair Value Measurements, page F-27

21.      Please revise to describe the inputs and techniques used in
determining the fair value of
         your level 2 invesments by major asset class. Refer to ASC
820-10-50-2.bbb.
13. Temporary Equity and Stockholders' Equity, page F-38

22.      Please provide your analysis supporting classification and valuation
of your Series A
         Convertible Preferred Stock as temporary equity as of December 31,
2020. Also tell us
         how you accounted for the change in conversion rate from $1.74 per
common share to
         $1.51 per common share at December 31, 2021. Refer to specific
guidance in your
         response.
14. Income Taxes, page F-39

23.      Please tell us why you do not have a larger valuation allowance
against your net deferred
         tax assets at both December 31, 2020 and 2021. In this regard, your
accumulated deficit at
         December 31, 2020 and losses in 2020 appear to be indicative of a
history of losses and a
         significant piece of negative evidence that is difficult to overcome
with an apparent one
         year of profitability in 2021 (see ASC 740-10-30-23). Given that you
did not record a
         significant valuation allowance reversal in 2020, in your response,
also tell us why a
         significant valuation allowance was not recorded against your deferred
tax assets at
         December 31, 2019.
15. Losses and Loss Adjustment Expenses, page F-41

24.      Please revise the rollforwards of your reserves for losses and LAE
beginning at the bottom
         of page F-41 to correct the apparent footing and decimal placement
errors. In this regard,
         for example, it appears that your net reserves at the beginning of
2021 should be $481,602
         thousand, not $48 thousand.
Short Duration Contract Disclosures, page F-42

25.      You disclose on page F-46 that your property and commercial auto
liability lines
         contributed 25.1% and 24.2% of your premiums written during 2021. You
also state on
         page F-42 that the prior year loss development of your multi-line and
short tail lines was
         due to commercial auto claims, and favorable loss emergence in your
property and
         accident and health product lines, respectively. Please tell us your
consideration of ASC
         944-40-50-4H in determining the level of disaggregation for your
incurred and paid loss
         development tables, as these lines within your tables appear to have
both a significant
         proportion of your business as well as differing development patterns.
 Andrew Robinson
Skyward Specialty Insurance Group, Inc.
May 19, 2022
Page 6
16. Premiums, page F-46

26.   Please reconcile the gross written premiums by line presented on page
F-46 with your
      disclosures by line on pages 4 and 83.
Schedule VI - Supplemental Information Concerning Property-Casualty Insurance
Operations,
page F-62

27.   Please tell us why the following amounts presented in this schedule are
inconsistent with
      those presented in your financial statements:
          The total of 2021 current and prior year losses and loss adjustment
expenses of
          $366,348,000 does not agree with the $354,411,000 presented on the
face of your
          statement of operations on page F-6.
          The total of 2020 current and prior year losses and loss adjustment
expenses of
          $351,398,000 does not agree with the $362,182,000 presented on the
face of your
          statement of operations on page F-6.
          Paid claims and claim adjustment expenses of $249,739,000 in 2021
does not agree
          with the $237,802,000 needed to properly roll forward your net
reserve balance in the
          table beginning at the bottom of page F-41.
Exhibits

28.   Refer to your disclosure on page 134 under "Transactions with the Westaim
Corporation
      and its affiliates" section. Please file the investment management
agreement with Arena
      Investors as an exhibit to your registration statement or tell us why you
have not filed it.
        You may contact Rolf Sundwall at (202) 551-3105 or Mark Brunhofer at
(202) 551-
3638 if you have questions regarding comments on the financial statements and
related
matters. Please contact Tonya K. Aldave at (202) 551-3601 or Susan Block at
(202) 551-
3210 with any other questions.



                                                             Sincerely,
FirstName LastNameAndrew Robinson
                                                     Division of Corporation
Finance
Comapany NameSkyward Specialty Insurance Group, Inc.
                                                     Office of Finance
May 19, 2022 Page 6
cc:       Patrick J. O'Malley, Esq.
FirstName LastName