diff --git a/src/EFCore.SqlServer/Migrations/SqlServerMigrationsSqlGenerator.cs b/src/EFCore.SqlServer/Migrations/SqlServerMigrationsSqlGenerator.cs
index c1d3e2b8a46..20f6721c791 100644
--- a/src/EFCore.SqlServer/Migrations/SqlServerMigrationsSqlGenerator.cs
+++ b/src/EFCore.SqlServer/Migrations/SqlServerMigrationsSqlGenerator.cs
@@ -1388,6 +1388,15 @@ protected override void Generate(
         builder.EndCommand();
     }
 
+    private enum ParsingState
+    {
+        Normal,
+        InBlockComment,
+        InSquareBrackets,
+        InDoubleQuotes,
+        InQuotes
+    }
+
     /// <summary>
     ///     Builds commands for the given <see cref="SqlOperation" /> by making calls on the given
     ///     <see cref="MigrationCommandListBuilder" />, and then terminates the final command.
@@ -1402,12 +1411,13 @@ protected override void Generate(SqlOperation operation, IModel? model, Migratio
             .Replace("\\\r\n", "")
             .Split(["\r\n", "\n"], StringSplitOptions.None);
 
-        var quoted = false;
+        var state = ParsingState.Normal;
         var batchBuilder = new StringBuilder();
         foreach (var line in preBatched)
         {
             var trimmed = line.TrimStart();
-            if (!quoted
+
+            if (state == ParsingState.Normal
                 && trimmed.StartsWith("GO", StringComparison.OrdinalIgnoreCase)
                 && (trimmed.Length == 2
                     || char.IsWhiteSpace(trimmed[2])))
@@ -1427,31 +1437,34 @@ protected override void Generate(SqlOperation operation, IModel? model, Migratio
             }
             else
             {
-                var commentStart = false;
-                foreach (var c in trimmed)
+                for (var i = 0; i < trimmed.Length; i++)
                 {
-                    switch (c)
+                    var c = trimmed[i];
+                    var next = i + 1 < trimmed.Length ? trimmed[i + 1] : '\0';
+
+                    if (state == ParsingState.Normal && c == '-' && next == '-')
                     {
-                        case '\'':
-                            quoted = !quoted;
-                            commentStart = false;
-                            break;
-                        case '-':
-                            if (!quoted)
-                            {
-                                if (commentStart)
-                                {
-                                    goto LineEnd;
-                                }
+                        goto LineEnd;
+                    }
 
-                                commentStart = true;
-                            }
+                    state = state switch
+                    {
+                        ParsingState.Normal when c == '\'' => ParsingState.InQuotes,
+                        ParsingState.Normal when c == '[' => ParsingState.InSquareBrackets,
+                        ParsingState.Normal when c == '"' => ParsingState.InDoubleQuotes,
+                        ParsingState.Normal when c == '/' && next == '*' => ConsumeAndReturn(ref i, ParsingState.InBlockComment),
 
-                            break;
-                        default:
-                            commentStart = false;
-                            break;
-                    }
+                        ParsingState.InQuotes when c == '\'' => ParsingState.Normal,
+
+                        ParsingState.InSquareBrackets when c == ']' && next == ']' => ConsumeAndReturn(ref i, ParsingState.InSquareBrackets),
+                        ParsingState.InSquareBrackets when c == ']' => ParsingState.Normal,
+
+                        ParsingState.InDoubleQuotes when c == '"' => ParsingState.Normal,
+
+                        ParsingState.InBlockComment when c == '*' && next == '/' => ConsumeAndReturn(ref i, ParsingState.Normal),
+
+                        _ => state
+                    };
                 }
 
                 LineEnd:
@@ -1461,6 +1474,12 @@ protected override void Generate(SqlOperation operation, IModel? model, Migratio
 
         AppendBatch(batchBuilder.ToString());
 
+        ParsingState ConsumeAndReturn(ref int index, ParsingState newState)
+        {
+            index++;
+            return newState;
+        }
+
         void AppendBatch(string batch)
         {
             if (!string.IsNullOrWhiteSpace(batch))
diff --git a/test/EFCore.SqlServer.FunctionalTests/Migrations/SqlServerMigrationsSqlGeneratorTest.cs b/test/EFCore.SqlServer.FunctionalTests/Migrations/SqlServerMigrationsSqlGeneratorTest.cs
index 22ddb64c6bf..effa2a16655 100644
--- a/test/EFCore.SqlServer.FunctionalTests/Migrations/SqlServerMigrationsSqlGeneratorTest.cs
+++ b/test/EFCore.SqlServer.FunctionalTests/Migrations/SqlServerMigrationsSqlGeneratorTest.cs
@@ -800,6 +800,517 @@ public override void SqlOperation()
 """);
     }
 
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_block_comment_with_single_quote()
+    {
+        Generate(
+            new SqlOperation { Sql = "/* It's a comment */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+/* It's a comment */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_multiline_block_comment_with_single_quote()
+    {
+        Generate(
+            new SqlOperation
+            {
+                Sql = "/* This is" + EOL + "   a multiline comment with ' quote */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;"
+            });
+
+        AssertSql(
+            """
+/* This is
+   a multiline comment with ' quote */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_block_comment_with_multiple_quotes()
+    {
+        Generate(
+            new SqlOperation
+            {
+                Sql = "/* It's a comment with 'multiple' quotes */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;"
+            });
+
+        AssertSql(
+            """
+/* It's a comment with 'multiple' quotes */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_block_comment_before_procedure()
+    {
+        Generate(
+            new SqlOperation
+            {
+                Sql = "/* It's a procedure */" + EOL + "CREATE PROCEDURE dbo.proc1 AS SELECT 1;" + EOL + "go" + EOL
+                    + "/* Another one */" + EOL + "CREATE PROCEDURE dbo.proc2 AS SELECT 2;"
+            });
+
+        AssertSql(
+            """
+/* It's a procedure */
+CREATE PROCEDURE dbo.proc1 AS SELECT 1;
+GO
+
+/* Another one */
+CREATE PROCEDURE dbo.proc2 AS SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_empty_block_comment()
+    {
+        Generate(
+            new SqlOperation { Sql = "/**/" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+/**/
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_nested_comments_and_strings()
+    {
+        Generate(
+            new SqlOperation
+            {
+                Sql = "/* Block comment */" + EOL + "SELECT 'string with '' escaped quotes';" + EOL + "go" + EOL
+                    + "-- Line comment" + EOL + "SELECT 1;"
+            });
+
+        AssertSql(
+            """
+/* Block comment */
+SELECT 'string with '' escaped quotes';
+GO
+
+-- Line comment
+SELECT 1;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_block_comment_after_string()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT 'test';" + EOL + "/* It's a comment */" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT 'test';
+/* It's a comment */
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_block_comment_with_asterisks()
+    {
+        Generate(
+            new SqlOperation
+            {
+                Sql = "/** It's a comment with extra stars **/" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;"
+            });
+
+        AssertSql(
+            """
+/** It's a comment with extra stars **/
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_line_comment_with_block_comment_start()
+    {
+        Generate(
+            new SqlOperation { Sql = "-- /*" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+-- /*
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_block_comment_with_line_comment_inside()
+    {
+        Generate(
+            new SqlOperation { Sql = "/* Block comment -- with line comment */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+/* Block comment -- with line comment */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_multiline_block_comment_with_go_on_separate_line()
+    {
+        Generate(
+            new SqlOperation
+            {
+                Sql = "/* Comment with" + EOL + "go" + EOL + "inside */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;"
+            });
+
+        AssertSql(
+            """
+/* Comment with
+go
+inside */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_square_bracket_identifier()
+    {
+        Generate(
+            new SqlOperation { Sql = "INSERT INTO [go] VALUES (1);" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+INSERT INTO [go] VALUES (1);
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_escaped_square_bracket_identifier()
+    {
+        Generate(
+            new SqlOperation { Sql = "INSERT INTO [g]]o] VALUES (1);" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+INSERT INTO [g]]o] VALUES (1);
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_double_quote_identifier()
+    {
+        Generate(
+            new SqlOperation { Sql = "INSERT INTO \"" + EOL + "go" + EOL + "\" VALUES (1);" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+INSERT INTO "
+go
+" VALUES (1);
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_quote_before_go()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT 'test\"';" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT 'test"';
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_forward_slash_before_go()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT 1/2;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT 1/2;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_asterisk_before_go()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT 1*2;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT 1*2;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_dash_before_go()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT 1-2;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT 1-2;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_square_bracket_before_go()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT [" + EOL + "column" + EOL + "];" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT [
+column
+];
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_double_quote_before_go()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT \"go\"\"lum\";" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT "go""lum";
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_line_comment_inside_quotes()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT '-- not a comment';" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT '-- not a comment';
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_line_comment_inside_square_brackets()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT [-- column];" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT [-- column];
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_line_comment_inside_double_quotes()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT \"-- column\";" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT "-- column";
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_brackets_inside_block_comment()
+    {
+        Generate(
+            new SqlOperation { Sql = "/* [bracket identifier */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+/* [bracket identifier */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_double_quotes_inside_block_comment()
+    {
+        Generate(
+            new SqlOperation { Sql = "/* \"double quote */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+/* "double quote */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_single_quote_inside_block_comment()
+    {
+        Generate(
+            new SqlOperation { Sql = "/* ' quote */" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+/* ' quote */
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_quotes_inside_line_comment()
+    {
+        Generate(
+            new SqlOperation { Sql = "-- 'quote' [bracket] \"double\"" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+-- 'quote' [bracket] "double"
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_brackets_inside_line_comment()
+    {
+        Generate(
+            new SqlOperation { Sql = "-- [column" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+-- [column
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_double_quotes_inside_line_comment()
+    {
+        Generate(
+            new SqlOperation { Sql = "-- \"column" + EOL + "SELECT 1;" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+-- "column
+SELECT 1;
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_escaped_quotes_in_string()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT 'test''s value';" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT 'test''s value';
+GO
+
+SELECT 2;
+""");
+    }
+
+    [ConditionalFact]
+    public virtual void SqlOperation_handles_multiple_delimiters_in_string()
+    {
+        Generate(
+            new SqlOperation { Sql = "SELECT '[bracket] and \"quote\"';" + EOL + "go" + EOL + "SELECT 2;" });
+
+        AssertSql(
+            """
+SELECT '[bracket] and "quote"';
+GO
+
+SELECT 2;
+""");
+    }
+
     public override void InsertDataOperation_all_args_spatial()
     {
         base.InsertDataOperation_all_args_spatial();