diff --git a/eng/helix/content/RunTests/ProcessUtil.cs b/eng/helix/content/RunTests/ProcessUtil.cs
index 8ac00bf829c3..416ec05a9087 100644
--- a/eng/helix/content/RunTests/ProcessUtil.cs
+++ b/eng/helix/content/RunTests/ProcessUtil.cs
@@ -59,6 +59,12 @@ public static Task CaptureDumpAsync(int pid, string dumpFilePath)
                 return Task.CompletedTask;
             }
 
+            if (!File.Exists($"{Environment.GetEnvironmentVariable("HELIX_WORKITEM_ROOT")}/dotnet-dump") &&
+                !File.Exists($"{Environment.GetEnvironmentVariable("HELIX_WORKITEM_ROOT")}/dotnet-dump.exe"))
+            {
+                return Task.CompletedTask;
+            }
+
             return RunAsync($"{Environment.GetEnvironmentVariable("HELIX_WORKITEM_ROOT")}/dotnet-dump", $"collect -p {pid} -o \"{dumpFilePath}\"");
         }
 
diff --git a/eng/helix/content/RunTests/TestRunner.cs b/eng/helix/content/RunTests/TestRunner.cs
index 2811fa3110d5..1a98743cab84 100644
--- a/eng/helix/content/RunTests/TestRunner.cs
+++ b/eng/helix/content/RunTests/TestRunner.cs
@@ -126,6 +126,15 @@ public async Task<bool> InstallDotnetToolsAsync()
         {
             try
             {
+                // Install dotnet-dump first so we can catch any failures from running dotnet after this (installing tools, running tests, etc.)
+                await ProcessUtil.RunAsync($"{Options.DotnetRoot}/dotnet",
+                    $"tool install dotnet-dump --tool-path {Options.HELIX_WORKITEM_ROOT} --version 5.0.0-*",
+                    environmentVariables: EnvironmentVariables,
+                    outputDataReceived: Console.WriteLine,
+                    errorDataReceived: Console.Error.WriteLine,
+                    throwOnError: false,
+                    cancellationToken: new CancellationTokenSource(TimeSpan.FromMinutes(2)).Token);
+
                 Console.WriteLine($"Adding current directory to nuget sources: {Options.HELIX_WORKITEM_ROOT}");
 
                 await ProcessUtil.RunAsync($"{Options.DotnetRoot}/dotnet",
@@ -161,13 +170,6 @@ await ProcessUtil.RunAsync($"{Options.DotnetRoot}/dotnet",
                     throwOnError: false,
                     cancellationToken: new CancellationTokenSource(TimeSpan.FromMinutes(2)).Token);
 
-                await ProcessUtil.RunAsync($"{Options.DotnetRoot}/dotnet",
-                    $"tool install dotnet-dump --tool-path {Options.HELIX_WORKITEM_ROOT} --version 5.0.0-*",
-                    environmentVariables: EnvironmentVariables,
-                    outputDataReceived: Console.WriteLine,
-                    errorDataReceived: Console.Error.WriteLine,
-                    throwOnError: false);
-
                 return true;
             }
             catch (Exception e)