diff --git a/src/Compilers/CSharp/Test/Emit/CSharpCompilerEmitTest.csproj b/src/Compilers/CSharp/Test/Emit/CSharpCompilerEmitTest.csproj
index a33d4ab2f03fd41f01ba04c95fceaab5c9e7d561..bde34582af0a08b8a55ca137d9445834261f024b 100644
--- a/src/Compilers/CSharp/Test/Emit/CSharpCompilerEmitTest.csproj
+++ b/src/Compilers/CSharp/Test/Emit/CSharpCompilerEmitTest.csproj
@@ -145,6 +145,7 @@
     <Compile Include="Emit\EmitMetadata.cs" />
     <Compile Include="Emit\EmitMetadataTestBase.cs" />
     <Compile Include="Attributes\EmitTestStrongNameProvider.cs" />
+    <Compile Include="Emit\EndToEndTests.cs" />
     <Compile Include="Emit\EntryPointTests.cs" />
     <Compile Include="Emit\NoPiaEmbedTypes.cs" />
     <Compile Include="Emit\OptionalArgumentsTests.cs" />
diff --git a/src/Compilers/CSharp/Test/Emit/Emit/EndToEndTests.cs b/src/Compilers/CSharp/Test/Emit/Emit/EndToEndTests.cs
new file mode 100644
index 0000000000000000000000000000000000000000..f4757fd1e811475f1bc753ababe3926f0a99e335
--- /dev/null
+++ b/src/Compilers/CSharp/Test/Emit/Emit/EndToEndTests.cs
@@ -0,0 +1,78 @@
+using Roslyn.Test.Utilities;
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Text;
+using System.Threading.Tasks;
+using Xunit;
+using Microsoft.CodeAnalysis.Test.Utilities;
+namespace Microsoft.CodeAnalysis.CSharp.UnitTests.Emit
+{
+    public class EndToEndTests: EmitMetadataTestBase
+    {
+        // This test is a canary attempting to make sure that we don't regress the # of fluent calls that 
+        // the compiler can handle.
+        [WorkItem(16669, "https://github.com/dotnet/roslyn/issues/16669")]
+        [Fact]
+        public void OverflowOnFluentCall()
+        {
+
+            int numberFluentCalls = 0;
+
+#if DEBUG
+            bool isDebug = true;
+#else
+            bool isDebug = false;
+#endif
+
+            switch (IntPtr.Size * 8) {
+                case 32 when isDebug:
+                    numberFluentCalls = 290;
+                    break;
+                case 32 when !isDebug:
+                    numberFluentCalls = 590;
+                    break;
+                case 64 when isDebug:
+                    numberFluentCalls = 110;
+                    break;
+                case 64 when !isDebug:
+                    numberFluentCalls = 310;
+                    break;
+                default:
+                    throw new Exception($"unexpected pointer size {IntPtr.Size}");
+            }
+
+
+            string MakeCode()
+            {
+                var builder = new StringBuilder();
+                builder.AppendLine(
+    @"class C {
+    C M(string x) { return this; }
+    void M2() {
+        new C()
+");
+                for (int i = 0; i < numberFluentCalls; i++)
+                {
+                    builder.AppendLine(@"            .M(""test"")");
+                }
+                builder.AppendLine(
+               @"            .M(""test"");
+    }
+}");
+                return builder.ToString();
+            }
+            var source = MakeCode();
+
+            var thread = new System.Threading.Thread(() =>
+            {
+                var options = new CSharpCompilationOptions(outputKind: OutputKind.DynamicallyLinkedLibrary, concurrentBuild: false);
+                var compilation = CreateCompilationWithMscorlib(source, options: options);
+                compilation.VerifyDiagnostics();
+                compilation.EmitToArray();
+            }, 0);
+            thread.Start();
+            thread.Join();
+        }
+    }
+}