diff --git a/src/Runner.Worker/ActionManager.cs b/src/Runner.Worker/ActionManager.cs
index 5b137baed..6dfa72c05 100644
--- a/src/Runner.Worker/ActionManager.cs
+++ b/src/Runner.Worker/ActionManager.cs
@@ -594,15 +594,22 @@ namespace GitHub.Runner.Worker
                     actionDownloadInfos = await jobServer.ResolveActionDownloadInfoAsync(executionContext.Global.Plan.ScopeIdentifier, executionContext.Global.Plan.PlanType, executionContext.Global.Plan.PlanId, new WebApi.ActionReferenceList { Actions = actionReferences }, executionContext.CancellationToken);
                     break;
                 }
-                catch (Exception ex) when (attempt < 3)
+                catch (Exception ex)
                 {
-                    executionContext.Output($"Failed to resolve action download info. Error: {ex.Message}");
-                    executionContext.Debug(ex.ToString());
-                    if (String.IsNullOrEmpty(Environment.GetEnvironmentVariable("_GITHUB_ACTION_DOWNLOAD_NO_BACKOFF")))
+                    if (attempt < 3)
                     {
-                        var backoff = BackoffTimerHelper.GetRandomBackoff(TimeSpan.FromSeconds(10), TimeSpan.FromSeconds(30));
-                        executionContext.Output($"Retrying in {backoff.TotalSeconds} seconds");
-                        await Task.Delay(backoff);
+                        executionContext.Output($"Failed to resolve action download info. Error: {ex.Message}");
+                        executionContext.Debug(ex.ToString());
+                        if (String.IsNullOrEmpty(Environment.GetEnvironmentVariable("_GITHUB_ACTION_DOWNLOAD_NO_BACKOFF")))
+                        {
+                            var backoff = BackoffTimerHelper.GetRandomBackoff(TimeSpan.FromSeconds(10), TimeSpan.FromSeconds(30));
+                            executionContext.Output($"Retrying in {backoff.TotalSeconds} seconds");
+                            await Task.Delay(backoff);
+                        }
+                    }
+                    else
+                    {
+                        throw new WebApi.FailedToResolveActionDownloadInfoException("Failed to resolve action download info.", ex);
                     }
                 }
             }
diff --git a/src/Runner.Worker/ExecutionContext.cs b/src/Runner.Worker/ExecutionContext.cs
index 449b43537..545340d36 100644
--- a/src/Runner.Worker/ExecutionContext.cs
+++ b/src/Runner.Worker/ExecutionContext.cs
@@ -918,6 +918,12 @@ namespace GitHub.Runner.Worker
             context.AddIssue(new Issue() { Type = IssueType.Error, Message = message });
         }
 
+        // Do not add a format string overload. See comment on ExecutionContext.Write().
+        public static void InfrastructureError(this IExecutionContext context, string message)
+        {
+            context.AddIssue(new Issue() { Type = IssueType.Error, Message = message, IsInfrastructureIssue = true});
+        }
+
         // Do not add a format string overload. See comment on ExecutionContext.Write().
         public static void Warning(this IExecutionContext context, string message)
         {
diff --git a/src/Runner.Worker/JobExtension.cs b/src/Runner.Worker/JobExtension.cs
index 1f51c57c8..d4f5d21b4 100644
--- a/src/Runner.Worker/JobExtension.cs
+++ b/src/Runner.Worker/JobExtension.cs
@@ -335,6 +335,14 @@ namespace GitHub.Runner.Worker
                     context.Result = TaskResult.Canceled;
                     throw;
                 }
+                catch (FailedToResolveActionDownloadInfoException ex) 
+                {
+                    // Log the error and fail the JobExtension Initialization.
+                    Trace.Error($"Caught exception from JobExtenion Initialization: {ex}");
+                    context.InfrastructureError(ex.Message);
+                    context.Result = TaskResult.Failed;
+                    throw;
+                }
                 catch (Exception ex)
                 {
                     // Log the error and fail the JobExtension Initialization.
diff --git a/src/Sdk/DTWebApi/WebApi/Exceptions.cs b/src/Sdk/DTWebApi/WebApi/Exceptions.cs
index c3615da7a..9e2435f5c 100644
--- a/src/Sdk/DTWebApi/WebApi/Exceptions.cs
+++ b/src/Sdk/DTWebApi/WebApi/Exceptions.cs
@@ -2458,4 +2458,23 @@ namespace GitHub.DistributedTask.WebApi
         {
         }
     }
+
+    [Serializable]
+    public sealed class FailedToResolveActionDownloadInfoException : DistributedTaskException
+    {
+        public FailedToResolveActionDownloadInfoException(String message)
+            : base(message)
+        {
+        }
+
+        public FailedToResolveActionDownloadInfoException(String message, Exception innerException)
+            : base(message, innerException)
+        {
+        }
+
+        private FailedToResolveActionDownloadInfoException(SerializationInfo info, StreamingContext context)
+            : base(info, context)
+        {
+        }
+    }
 }
diff --git a/src/Sdk/DTWebApi/WebApi/Issue.cs b/src/Sdk/DTWebApi/WebApi/Issue.cs
index 4875ca5a1..af4d2f850 100644
--- a/src/Sdk/DTWebApi/WebApi/Issue.cs
+++ b/src/Sdk/DTWebApi/WebApi/Issue.cs
@@ -17,6 +17,7 @@ namespace GitHub.DistributedTask.WebApi
             this.Type = issueToBeCloned.Type;
             this.Category = issueToBeCloned.Category;
             this.Message = issueToBeCloned.Message;
+            this.IsInfrastructureIssue = issueToBeCloned.IsInfrastructureIssue;
 
             if (issueToBeCloned.m_data != null)
             {
@@ -48,6 +49,13 @@ namespace GitHub.DistributedTask.WebApi
             set;
         }
 
+        [DataMember(Order = 4)]
+        public bool? IsInfrastructureIssue
+        {
+            get;
+            set;
+        }
+
         public IDictionary<String, String> Data
         {
             get