diff --git a/CodeConverter/CSharp/MethodBodyExecutableStatementVisitor.cs b/CodeConverter/CSharp/MethodBodyExecutableStatementVisitor.cs
index bc48a7dc..b526d07e 100644
--- a/CodeConverter/CSharp/MethodBodyExecutableStatementVisitor.cs
+++ b/CodeConverter/CSharp/MethodBodyExecutableStatementVisitor.cs
@@ -861,7 +861,8 @@ public override async Task<SyntaxList<StatementSyntax>> VisitSelectBlock(VBSynta
                         lowerBoundCheck = ComparisonAdjustedForStringComparison(node, range.LowerBound, caseTypeInfo, lowerBound, csCaseVar, switchExprTypeInfo, ComparisonKind.LessThanOrEqual);
                     } else {
                         lowerBound = CommonConversions.TypeConversionAnalyzer.AddExplicitConversion(range.LowerBound, lowerBound);
-                        lowerBoundCheck = SyntaxFactory.BinaryExpression(SyntaxKind.LessThanOrEqualExpression, lowerBound, csCaseVar);
+                        var (lowerBoundForComparison, csCaseVarForLower) = CastBothToUnderlyingTypeIfEnum(switchExprTypeInfo.ConvertedType, lowerBound, csCaseVar);
+                        lowerBoundCheck = SyntaxFactory.BinaryExpression(SyntaxKind.LessThanOrEqualExpression, lowerBoundForComparison, csCaseVarForLower);
                     }
                     var upperBound = await range.UpperBound.AcceptAsync<ExpressionSyntax>(_expressionVisitor);
                     ExpressionSyntax upperBoundCheck;
@@ -870,7 +871,8 @@ public override async Task<SyntaxList<StatementSyntax>> VisitSelectBlock(VBSynta
                         upperBoundCheck = ComparisonAdjustedForStringComparison(node, range.UpperBound, switchExprTypeInfo, csCaseVar, upperBound, caseTypeInfo, ComparisonKind.LessThanOrEqual);
                     } else {
                         upperBound = CommonConversions.TypeConversionAnalyzer.AddExplicitConversion(range.UpperBound, upperBound);
-                        upperBoundCheck = SyntaxFactory.BinaryExpression(SyntaxKind.LessThanOrEqualExpression, csCaseVar, upperBound);
+                        var (csCaseVarForUpper, upperBoundForComparison) = CastBothToUnderlyingTypeIfEnum(switchExprTypeInfo.ConvertedType, csCaseVar, upperBound);
+                        upperBoundCheck = SyntaxFactory.BinaryExpression(SyntaxKind.LessThanOrEqualExpression, csCaseVarForUpper, upperBoundForComparison);
                     }
                     var withinBounds = SyntaxFactory.BinaryExpression(SyntaxKind.LogicalAndExpression, lowerBoundCheck, upperBoundCheck);
                     labels.Add(VarWhen(varName, withinBounds));
@@ -930,6 +932,21 @@ bool IsExitStatement(StatementSyntax node)
     private static bool IsEnumOrNullableEnum(ITypeSymbol convertedType) =>
         convertedType?.IsEnumType() == true || convertedType?.GetNullableUnderlyingType()?.IsEnumType() == true;
 
+    /// <summary>
+    /// When the switch expression is an enum, C# does not support &lt;= comparisons directly on enum values.
+    /// Cast both sides to the enum's underlying integer type so the comparison compiles.
+    /// </summary>
+    private (ExpressionSyntax Left, ExpressionSyntax Right) CastBothToUnderlyingTypeIfEnum(ITypeSymbol switchExprType, ExpressionSyntax left, ExpressionSyntax right)
+    {
+        var enumType = switchExprType?.IsEnumType() == true ? switchExprType as INamedTypeSymbol
+            : switchExprType?.GetNullableUnderlyingType() as INamedTypeSymbol;
+        if (enumType?.EnumUnderlyingType is not { } underlyingType) {
+            return (left, right);
+        }
+        var typeSyntax = CommonConversions.GetTypeSyntax(underlyingType);
+        return (ValidSyntaxFactory.CastExpression(typeSyntax, left), ValidSyntaxFactory.CastExpression(typeSyntax, right));
+    }
+
     private static CasePatternSwitchLabelSyntax VarWhen(SyntaxToken varName, ExpressionSyntax binaryExp)
     {
         var patternMatch = ValidSyntaxFactory.VarPattern(varName);
diff --git a/Tests/CSharp/StatementTests/MethodStatementTests.cs b/Tests/CSharp/StatementTests/MethodStatementTests.cs
index bc20f218..85a19e05 100644
--- a/Tests/CSharp/StatementTests/MethodStatementTests.cs
+++ b/Tests/CSharp/StatementTests/MethodStatementTests.cs
@@ -1111,6 +1111,50 @@ public static string TimeAgo(int daysAgo)
 CS0825: The contextual keyword 'var' may only appear within a local variable declaration or in script code");
     }
 
+    [Fact]
+    public async Task SelectCaseWithEnumRangeAsync()
+    {
+        await TestConversionVisualBasicToCSharpAsync(@"Public Class TestClass
+    Enum UserLevel
+        City_Staff
+        Admin
+        Fixity_ROOT
+    End Enum
+
+    Shared Function IsPrivileged(level As UserLevel) As Boolean
+        Select Case level
+            Case UserLevel.City_Staff To UserLevel.Fixity_ROOT
+                Return True
+        End Select
+        Return False
+    End Function
+End Class", @"
+public partial class TestClass
+{
+    public enum UserLevel
+    {
+        City_Staff,
+        Admin,
+        Fixity_ROOT
+    }
+
+    public static bool IsPrivileged(UserLevel level)
+    {
+        switch (level)
+        {
+            case var @case when (int)UserLevel.City_Staff <= (int)@case && (int)@case <= (int)UserLevel.Fixity_ROOT:
+                {
+                    return true;
+                }
+        }
+
+        return false;
+    }
+}
+1 target compilation errors:
+CS0825: The contextual keyword 'var' may only appear within a local variable declaration or in script code");
+    }
+
     [Fact]
     public async Task SelectCaseWithStringAsync()
     {