How to fix Error 2355 on Windows Server 2025 / Windows 11

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Why This Error Happens

Error 2355 occurs when the T-SQL parser encounters an IF block or CASE statement where the expected ELSE keyword is either missing, misplaced, or malformed due to a syntax mismatch. This typically happens when a script contains unbalanced BEGIN...END blocks, a misplaced semicolon terminating the IF clause prematurely, or when legacy scripts generated by older SSMS versions are run against the stricter parser in SQL Server 2025. It can also surface during automated deployment pipelines where a templating engine incorrectly injects a newline or comment between the IF condition and its corresponding ELSE clause.

Step-by-Step Resolution Guide

Step 1: Isolate the Offending Script Block

  • Open the specific stored procedure, trigger, or script referenced in the SQL Server Error Log using SQL Server Management Studio (SSMS) 21.
  • Locate the exact line number provided in the error details (usually found in the “Procedure” column of the error output).
  • Check for a semicolon (;) immediately following the IF condition’s END statement, as this breaks the association with the subsequent ELSE.

Step 2: Validate Block Structure and Syntax

  • Ensure every BEGIN keyword within the IF statement has a corresponding END keyword before the ELSE is declared.
  • Remove any comments (-- or /* */) placed directly between the END of the IF block and the ELSE keyword, as the 2025 parser can sometimes misinterpret complex nested comments in this specific gap.
  • Rewrite the conditional logic using explicit BEGIN...END blocks for both the IF and ELSE sections to eliminate ambiguity:
  IF (1=1)
  BEGIN
      PRINT 'True';
  END
  ELSE
  BEGIN
      PRINT 'False';
  END

Step 3: Clear the Plan Cache and Re-deploy

  • Clear the procedure cache to ensure the old, broken query plan is not being reused during compilation attempts.
  • Run the following command in a new query window: DBCC FREEPROCCACHE;
  • Re-deploy the corrected script or recompile the stored procedure using EXEC sp_recompile 'YourProcedureName';

Step 4: Check Compatibility Level Settings

  • Verify the database compatibility level is correctly set, as SQL Server 2025 introduces stricter parsing under higher compatibility levels (170).
  • Navigate to Database Properties > Options in SSMS and check the “Compatibility Level” dropdown.
  • If the script was written for an older engine, temporarily test compatibility level 160 to confirm if the parser behavior changes.

Alternative or Verification Steps

  • Execute the corrected script via sqlcmd from a command prompt to verify it parses without errors outside of the GUI environment: sqlcmd -S localhost -i C:\Scripts\FixedScript.sql
  • If the error persists after fixing syntax, use the SSMS Query > Parse feature (Ctrl+F5) to validate the T-SQL syntax tree before execution to pinpoint hidden whitespace or encoding issues.