diff --git a/src/Runner.Common/Constants.cs b/src/Runner.Common/Constants.cs
index fb4d79951..7e630bd89 100644
--- a/src/Runner.Common/Constants.cs
+++ b/src/Runner.Common/Constants.cs
@@ -175,6 +175,9 @@ namespace GitHub.Runner.Common
             public static readonly string UnsupportedStopCommandTokenDisabled = "You cannot use a endToken that is an empty string, the string 'pause-logging', or another workflow command. For more information see: https://docs.github.com/actions/learn-github-actions/workflow-commands-for-github-actions#example-stopping-and-starting-workflow-commands or opt into insecure command execution by setting the `ACTIONS_ALLOW_UNSECURE_STOPCOMMAND_TOKENS` environment variable to `true`.";
             public static readonly string UnsupportedSummarySize = "$GITHUB_STEP_SUMMARY upload aborted, supports content up to a size of {0}k, got {1}k. For more information see: https://docs.github.com/actions/using-workflows/workflow-commands-for-github-actions#adding-a-markdown-summary";
             public static readonly string SummaryUploadError = "$GITHUB_STEP_SUMMARY upload aborted, an error occurred when uploading the summary. For more information see: https://docs.github.com/actions/using-workflows/workflow-commands-for-github-actions#adding-a-markdown-summary";
+            public static readonly string DetectedNodeAfterEndOfLifeMessage = "Node.js 16 actions are deprecated. Please update the following actions to use Node.js 20: {0}. For more information see: https://github.blog/changelog/2023-09-22-github-actions-transitioning-from-node-16-to-node-20/.";
+            public static readonly string DeprecatedNodeDetectedAfterEndOfLifeActions = "DeprecatedNodeActionsMessageWarnings";
+            public static readonly string DeprecatedNodeVersion = "node16";
             public static readonly string EnforcedNode12DetectedAfterEndOfLife = "The following actions uses node12 which is deprecated and will be forced to run on node16: {0}. For more info: https://github.blog/changelog/2023-06-13-github-actions-all-actions-will-run-on-node16-instead-of-node12-by-default/";
             public static readonly string EnforcedNode12DetectedAfterEndOfLifeEnvVariable = "Node16ForceActionsWarnings";
         }
diff --git a/src/Runner.Worker/ActionManager.cs b/src/Runner.Worker/ActionManager.cs
index f5575684b..56196c6e4 100644
--- a/src/Runner.Worker/ActionManager.cs
+++ b/src/Runner.Worker/ActionManager.cs
@@ -854,6 +854,11 @@ namespace GitHub.Runner.Worker
                             Trace.Info("Action download has been cancelled.");
                             throw;
                         }
+                        catch (OperationCanceledException ex) when (!executionContext.CancellationToken.IsCancellationRequested && retryCount >= 2)
+                        {
+                            Trace.Info($"Action download final retry timeout after {timeoutSeconds} seconds.");
+                            throw new TimeoutException($"Action '{link}' download has timed out. Error: {ex.Message}");
+                        }
                         catch (ActionNotFoundException)
                         {
                             Trace.Info($"The action at '{link}' does not exist");
diff --git a/src/Runner.Worker/Handlers/NodeScriptActionHandler.cs b/src/Runner.Worker/Handlers/NodeScriptActionHandler.cs
index c5bc7fd6e..32d4eb084 100644
--- a/src/Runner.Worker/Handlers/NodeScriptActionHandler.cs
+++ b/src/Runner.Worker/Handlers/NodeScriptActionHandler.cs
@@ -134,6 +134,28 @@ namespace GitHub.Runner.Worker.Handlers
             // Remove environment variable that may cause conflicts with the node within the runner.
             Environment.Remove("NODE_ICU_DATA"); // https://github.com/actions/runner/issues/795
 
+            if (string.Equals(Data.NodeVersion, Constants.Runner.DeprecatedNodeVersion, StringComparison.OrdinalIgnoreCase) && (ExecutionContext.Global.Variables.GetBoolean(Constants.Runner.Features.Node16Warning) ?? false))
+            {
+                var repoAction = Action as RepositoryPathReference;
+                var warningActions = new HashSet<string>();
+                if (ExecutionContext.Global.Variables.TryGetValue(Constants.Runner.DeprecatedNodeDetectedAfterEndOfLifeActions, out var deprecatedNodeWarnings))
+                {
+                    warningActions = StringUtil.ConvertFromJson<HashSet<string>>(deprecatedNodeWarnings);
+                }
+
+                if (string.IsNullOrEmpty(repoAction.Name))
+                {
+                    // local actions don't have a 'Name'
+                    warningActions.Add(repoAction.Path);
+                }
+                else
+                {
+                    warningActions.Add($"{repoAction.Name}/{repoAction.Path ?? string.Empty}".TrimEnd('/') + $"@{repoAction.Ref}");
+                }
+
+                ExecutionContext.Global.Variables.Set(Constants.Runner.DeprecatedNodeDetectedAfterEndOfLifeActions, StringUtil.ConvertToJson(warningActions));
+            }
+
             using (var stdoutManager = new OutputManager(ExecutionContext, ActionCommandManager))
             using (var stderrManager = new OutputManager(ExecutionContext, ActionCommandManager))
             {
diff --git a/src/Runner.Worker/JobRunner.cs b/src/Runner.Worker/JobRunner.cs
index cde358dcb..aa6580402 100644
--- a/src/Runner.Worker/JobRunner.cs
+++ b/src/Runner.Worker/JobRunner.cs
@@ -276,6 +276,12 @@ namespace GitHub.Runner.Worker
         {
             jobContext.Debug($"Finishing: {message.JobDisplayName}");
             TaskResult result = jobContext.Complete(taskResult);
+            if (jobContext.Global.Variables.TryGetValue(Constants.Runner.DeprecatedNodeDetectedAfterEndOfLifeActions, out var deprecatedNodeWarnings))
+            {
+                var actions = string.Join(", ", StringUtil.ConvertFromJson<HashSet<string>>(deprecatedNodeWarnings));
+                jobContext.Warning(string.Format(Constants.Runner.DetectedNodeAfterEndOfLifeMessage, actions));
+            }
+
             if (jobContext.Global.Variables.TryGetValue(Constants.Runner.EnforcedNode12DetectedAfterEndOfLifeEnvVariable, out var node16ForceWarnings))
             {
                 var actions = string.Join(", ", StringUtil.ConvertFromJson<HashSet<string>>(node16ForceWarnings));
@@ -375,6 +381,12 @@ namespace GitHub.Runner.Worker
                 }
             }
 
+            if (jobContext.Global.Variables.TryGetValue(Constants.Runner.DeprecatedNodeDetectedAfterEndOfLifeActions, out var deprecatedNodeWarnings))
+            {
+                var actions = string.Join(", ", StringUtil.ConvertFromJson<HashSet<string>>(deprecatedNodeWarnings));
+                jobContext.Warning(string.Format(Constants.Runner.DetectedNodeAfterEndOfLifeMessage, actions));
+            }
+
             if (jobContext.Global.Variables.TryGetValue(Constants.Runner.EnforcedNode12DetectedAfterEndOfLifeEnvVariable, out var node16ForceWarnings))
             {
                 var actions = string.Join(", ", StringUtil.ConvertFromJson<HashSet<string>>(node16ForceWarnings));