Washington, D.C. 20549 AMENDMENT NO. 1 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 As filed with the Securities and Exchange Commission on June 6, 2023. UNITED STATES SECURITIES AND EXCHANGE COMMISSION SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exact name of Registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 6331 (Primary Standard Industrial Classification Code Number) 14-1957288 (I.R.S. Employer Identification Number) 800 Gessn ...

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on June 5, 2023. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exact name of Registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 6331 (Primary Standard Industrial Classification Code Number) 14-1957288 (I.R.S. Employer Identifi ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ________________________________ (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from ____________ to ____________ Commission file number 001-41591 SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exac ...

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K __________________________________________ (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _________ to _________ Commission file number 001-41591 __________________________________________ SKY ...

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on January 4, 2023. Registration No. 333-268326 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 1 TO FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exact name of Registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 6331 (Primary Standard Industrial Classification Code Number) 14-19572 ...