diff --git a/src/System.Diagnostics.Debug/tests/DebugTests.cs b/src/System.Diagnostics.Debug/tests/DebugTests.cs
index da41ae897700..c0abd37323dc 100644
--- a/src/System.Diagnostics.Debug/tests/DebugTests.cs
+++ b/src/System.Diagnostics.Debug/tests/DebugTests.cs
@@ -41,7 +41,7 @@ protected void VerifyLogged(Action test, string expectedOutput)
 
             // First use our test logger to verify the output
             var originalWriteCoreHook = writeCoreHook.GetValue(null);
-            writeCoreHook.SetValue(null, new Action<string>(WriteLogger.s_instance.MockWrite));
+            writeCoreHook.SetValue(null, new Action<string>(WriteLogger.s_instance.WriteCore));
 
             try
             {
@@ -62,11 +62,12 @@ protected void VerifyLogged(Action test, string expectedOutput)
         protected void VerifyAssert(Action test, params string[] expectedOutputStrings)
         {
             FieldInfo writeCoreHook = typeof(DebugProvider).GetField("s_WriteCore", BindingFlags.Static | BindingFlags.NonPublic);
-            s_defaultProvider = Debug.SetProvider(WriteLogger.s_instance);
-            WriteLogger.s_instance.OriginalProvider = s_defaultProvider;
-            
             var originalWriteCoreHook = writeCoreHook.GetValue(null);
-            writeCoreHook.SetValue(null, new Action<string>(WriteLogger.s_instance.MockWrite));
+            writeCoreHook.SetValue(null, new Action<string>(WriteLogger.s_instance.WriteCore));
+            
+            FieldInfo failCoreHook = typeof(DebugProvider).GetField("s_FailCore", BindingFlags.Static | BindingFlags.NonPublic);
+            var originalFailCoreHook = failCoreHook.GetValue(null);
+            failCoreHook.SetValue(null, new Action<string, string, string, string>(WriteLogger.s_instance.FailCore));
 
             try
             {
@@ -82,19 +83,16 @@ protected void VerifyAssert(Action test, params string[] expectedOutputStrings)
             finally
             {
                 writeCoreHook.SetValue(null, originalWriteCoreHook);
-                Debug.SetProvider(s_defaultProvider);
+                failCoreHook.SetValue(null, originalFailCoreHook);
             }
         }
 
-        private static DebugProvider s_defaultProvider;
-        private class WriteLogger : DebugProvider
+        internal class WriteLogger
         {
             public static readonly WriteLogger s_instance = new WriteLogger();
 
             private WriteLogger() { }
 
-            public DebugProvider OriginalProvider { get; set; }
-
             public string LoggedOutput { get; private set; }
 
             public string AssertUIOutput { get; private set; }
@@ -105,24 +103,12 @@ public void Clear()
                 AssertUIOutput = string.Empty;
             }
 
-            public override void ShowDialog(string stackTrace, string message, string detailMessage, string errorSource)
+            public void FailCore(string stackTrace, string message, string detailMessage, string errorSource)
             {
                 AssertUIOutput += stackTrace + message + detailMessage + errorSource;
             }
 
-            public override void OnIndentLevelChanged(int indentLevel)
-            {
-                OriginalProvider.OnIndentLevelChanged(indentLevel);
-            }
-
-            public override void OnIndentSizeChanged(int indentSize)
-            {
-                OriginalProvider.OnIndentLevelChanged(indentSize);
-            }
-            public override void Write(string message) { OriginalProvider.Write(message); }
-            public override void WriteLine(string message) { OriginalProvider.WriteLine(message); }
-
-            public void MockWrite(string message)
+            public void WriteCore(string message)
             {
                 Assert.NotNull(message);
                 LoggedOutput += message;
diff --git a/src/System.Diagnostics.Debug/tests/DebugTestsUsingListeners.cs b/src/System.Diagnostics.Debug/tests/DebugTestsUsingListeners.cs
index 992a861d741b..2e46f7a7c84d 100644
--- a/src/System.Diagnostics.Debug/tests/DebugTestsUsingListeners.cs
+++ b/src/System.Diagnostics.Debug/tests/DebugTestsUsingListeners.cs
@@ -244,5 +244,62 @@ public void TraceWriteLineIf()
             VerifyLogged(() => Trace.WriteLineIf(true, "logged", "category"), "category: logged" + Environment.NewLine);
             VerifyLogged(() => Trace.WriteLineIf(false, "logged", "category"), "");     
         }
+
+        [Fact]
+        public void Trace_AssertUiEnabledFalse_SkipsFail()
+        {
+            var initialListener = (DefaultTraceListener)Trace.Listeners[0];
+            Trace.Listeners.Clear();
+            Trace.Fail("Skips fail fast");
+            Debug.Fail("Skips fail fast");
+
+            initialListener.AssertUiEnabled = false;
+            Trace.Listeners.Add(initialListener);
+            Debug.Fail("Skips fail fast");
+            Trace.Fail("Skips fail fast");
+
+            var myListener = new MyTraceListener();
+            string expectedDialog = $"Mock dialog - message: short, detailed message: long";
+            Trace.Listeners.Clear();
+            Trace.Listeners.Add(myListener);
+
+            try
+            {
+                myListener.AssertUiEnabled = false;
+                Debug.Fail("short", "long");
+                Assert.Equal("", myListener.OutputString);
+                Trace.Fail("short", "long");
+                Assert.Equal("", myListener.OutputString);
+
+                myListener.AssertUiEnabled = true;
+                Debug.Fail("short", "long");
+                Assert.Equal(expectedDialog, myListener.OutputString);
+                Trace.Fail("short", "long");
+                Assert.Equal(expectedDialog + expectedDialog, myListener.OutputString);
+            }
+            finally
+            {
+                Trace.Listeners.Clear();
+                Trace.Listeners.Add(initialListener);
+            }
+        }
+
+        class MyTraceListener : DefaultTraceListener
+        {
+            private void FailCore(string stackTrace, string message, string detailMessage, string errorSource) 
+            {
+                OutputString += $"Mock dialog - message: {message}, detailed message: {detailMessage}";
+            }
+            public string OutputString { get; private set; } = string.Empty;
+
+            public override void Fail(string message, string detailMessage)
+            {
+                WriteLine(message, detailMessage);
+                if (AssertUiEnabled)
+                {
+                    FailCore(string.Empty, message, detailMessage, "Assertion Failed");
+                }
+            }
+        }
     }
 }
diff --git a/src/System.Diagnostics.TraceSource/src/System/Diagnostics/DefaultTraceListener.cs b/src/System.Diagnostics.TraceSource/src/System/Diagnostics/DefaultTraceListener.cs
index 0c653310c02b..7207bc77ce1d 100644
--- a/src/System.Diagnostics.TraceSource/src/System/Diagnostics/DefaultTraceListener.cs
+++ b/src/System.Diagnostics.TraceSource/src/System/Diagnostics/DefaultTraceListener.cs
@@ -89,16 +89,10 @@ public override void Fail(string message, string detailMessage)
             {
                 stackTrace = "";
             }
-            // Tracked by #32955: WriteAssert should write "stackTrace" rather than string.Empty. 
-            WriteAssert(string.Empty, message, detailMessage);
+            WriteAssert(stackTrace, message, detailMessage);
             if (AssertUiEnabled)
             {
-                // Tracked by #32955: Currently AssertUiEnabled is true by default but we are not calling Enviroment.FailFast as Debug.Fail does 
-                // s_provider.ShowDialog(stackTrace, message, detailMessage, "Assertion Failed");
-            }
-            if (Debugger.IsAttached)
-            {
-                Debugger.Break();
+                DebugProvider.FailCore(stackTrace, message, detailMessage, "Assertion Failed");
             }
         }
 
diff --git a/src/System.Diagnostics.TraceSource/src/System/Diagnostics/TraceInternal.cs b/src/System.Diagnostics.TraceSource/src/System/Diagnostics/TraceInternal.cs
index 832701d669ae..7ef82101f2c8 100644
--- a/src/System.Diagnostics.TraceSource/src/System/Diagnostics/TraceInternal.cs
+++ b/src/System.Diagnostics.TraceSource/src/System/Diagnostics/TraceInternal.cs
@@ -13,6 +13,7 @@ internal static class TraceInternal
     {
         private class TraceProvider : DebugProvider
         {
+            public override void Fail(string message, string detailMessage) { TraceInternal.Fail(message, detailMessage); }
             public override void OnIndentLevelChanged(int indentLevel)
             {
                 lock (TraceInternal.critSec)