diff --git a/src/ILCompiler.WebAssembly/src/CodeGen/EvaluationStack.cs b/src/ILCompiler.WebAssembly/src/CodeGen/EvaluationStack.cs
index 0e55fe23029..685622d2fcb 100644
--- a/src/ILCompiler.WebAssembly/src/CodeGen/EvaluationStack.cs
+++ b/src/ILCompiler.WebAssembly/src/CodeGen/EvaluationStack.cs
@@ -577,7 +577,7 @@ protected override LLVMValueRef ValueAsTypeInternal(LLVMTypeRef type, LLVMBuilde
             LLVMTypeRef origLLVMType = ILImporter.GetLLVMTypeForTypeDesc(Type);
             LLVMValueRef value = _importer.LoadTemp(LocalIndex, origLLVMType);
 
-            return ILImporter.CastIfNecessary(builder, value, type);
+            return ILImporter.CastIfNecessary(builder, value, type, unsigned: !signExtend);
         }
 
         public override StackEntry Duplicate(LLVMBuilderRef builder)
diff --git a/src/ILCompiler.WebAssembly/src/CodeGen/ILToWebAssemblyImporter.cs b/src/ILCompiler.WebAssembly/src/CodeGen/ILToWebAssemblyImporter.cs
index c08f9658a98..76d29e7de35 100644
--- a/src/ILCompiler.WebAssembly/src/CodeGen/ILToWebAssemblyImporter.cs
+++ b/src/ILCompiler.WebAssembly/src/CodeGen/ILToWebAssemblyImporter.cs
@@ -4054,6 +4054,7 @@ bool TypeNeedsSignExtension(TypeDesc targetType)
             if (enumCleanTargetType != null && targetType.IsPrimitive)
             {
                 if (enumCleanTargetType.IsWellKnownType(WellKnownType.Byte) ||
+                    enumCleanTargetType.IsWellKnownType(WellKnownType.Boolean) ||
                     enumCleanTargetType.IsWellKnownType(WellKnownType.Char) ||
                     enumCleanTargetType.IsWellKnownType(WellKnownType.UInt16) ||
                     enumCleanTargetType.IsWellKnownType(WellKnownType.UInt32) ||
@@ -4145,7 +4146,7 @@ private void ImportCompareOperation(ILOpcode opcode)
                 }
             }
 
-            PushExpression(StackValueKind.Int32, "cmpop", result, GetWellKnownType(WellKnownType.SByte));
+            PushExpression(StackValueKind.Int32, "cmpop", result, GetWellKnownType(WellKnownType.UInt32));
         }
 
         private void ImportConvert(WellKnownType wellKnownType, bool checkOverflow, bool unsigned)
diff --git a/tests/src/Simple/HelloWasm/Program.cs b/tests/src/Simple/HelloWasm/Program.cs
index eddf007da00..523a8e15e8b 100644
--- a/tests/src/Simple/HelloWasm/Program.cs
+++ b/tests/src/Simple/HelloWasm/Program.cs
@@ -370,6 +370,8 @@ private static unsafe int Main(string[] args)
 
         TestGetSystemArrayEEType();
 
+        TestBoolCompare();
+
         // This test should remain last to get other results before stopping the debugger
         PrintLine("Debugger.Break() test: Ok if debugger is open and breaks.");
         System.Diagnostics.Debugger.Break();
@@ -2922,6 +2924,14 @@ static void TestGetSystemArrayEEType()
         EndTest(true); // testing compilation 
     }
 
+    static void TestBoolCompare()
+    {
+        StartTest("Test Bool.Equals");
+        bool expected = true;
+        bool actual = true;
+        EndTest(expected.Equals(actual));
+    }
+
     static ushort ReadUInt16()
     {
         // something with MSB set