diff --git a/src/Analyzers/CSharp/Tests/RemoveUnnecessaryCast/RemoveUnnecessaryCastTests.cs b/src/Analyzers/CSharp/Tests/RemoveUnnecessaryCast/RemoveUnnecessaryCastTests.cs
index c04f806482679..6ea90acdd4ec4 100644
--- a/src/Analyzers/CSharp/Tests/RemoveUnnecessaryCast/RemoveUnnecessaryCastTests.cs
+++ b/src/Analyzers/CSharp/Tests/RemoveUnnecessaryCast/RemoveUnnecessaryCastTests.cs
@@ -13757,7 +13757,7 @@ void M2()
     }
 
     [Fact, WorkItem("https://github.com/dotnet/roslyn/issues/71926")]
-    public async Task NecessaryDelegateCast()
+    public async Task NecessaryDelegateCast1()
     {
         await new VerifyCS.Test
         {
@@ -13778,4 +13778,34 @@ static void Main(string[] args)
             ReferenceAssemblies = ReferenceAssemblies.Net.Net80,
         }.RunAsync();
     }
+
+    [Fact, WorkItem("https://github.com/dotnet/roslyn/issues/72134")]
+    public async Task NecessaryDelegateCast2()
+    {
+        await new VerifyCS.Test
+        {
+            TestCode = """
+                using System;
+
+                public class MyClass
+                {
+                    static void Main()
+                    {
+                        Goo f = (Action)(() => { }); // IDE0004: Cast is redundant.
+
+                    }
+                }
+
+                public class Goo
+                {
+                    public static implicit operator Goo(Action value)
+                    {
+                        return default!;
+                    }
+                }
+                """,
+            LanguageVersion = LanguageVersion.CSharp12,
+            ReferenceAssemblies = ReferenceAssemblies.Net.Net80,
+        }.RunAsync();
+    }
 }
diff --git a/src/Workspaces/SharedUtilitiesAndExtensions/Compiler/CSharp/Simplification/Simplifiers/CastSimplifier.cs b/src/Workspaces/SharedUtilitiesAndExtensions/Compiler/CSharp/Simplification/Simplifiers/CastSimplifier.cs
index c7f04caee0265..ae4d58e83e4bb 100644
--- a/src/Workspaces/SharedUtilitiesAndExtensions/Compiler/CSharp/Simplification/Simplifiers/CastSimplifier.cs
+++ b/src/Workspaces/SharedUtilitiesAndExtensions/Compiler/CSharp/Simplification/Simplifiers/CastSimplifier.cs
@@ -327,6 +327,14 @@ private static bool IsConversionCastSafeToRemove(
             if (isNullLiteralCast && !originalConvertedType.IsReferenceType && !originalConvertedType.IsNullable())
                 return false;
 
+            // SomeType s = (Action)(() => {});  // Where there's a user defined conversion from Action->SomeType.
+            //
+            // This cast is necessary.  The language does not allow lambdas to be directly converted to the destination
+            // type without explicitly stating the intermediary reified delegate type.
+            var isAnonymousFunctionCast = castedExpressionNode.WalkDownParentheses() is AnonymousFunctionExpressionSyntax;
+            if (isAnonymousFunctionCast && originalConversion.IsUserDefined)
+                return false;
+
             // So far, this looks potentially possible to remove.  Now, actually do the removal and get the
             // semantic model for the rewritten code so we can check it to make sure semantics were preserved.
             var (rewrittenSemanticModel, rewrittenExpression) = GetSemanticModelWithCastRemoved(