diff --git a/src/Agent/AutopilotMonitor.Agent/Program.Configuration.cs b/src/Agent/AutopilotMonitor.Agent/Program.Configuration.cs
index b8e4983e..bd41f3b2 100644
--- a/src/Agent/AutopilotMonitor.Agent/Program.Configuration.cs
+++ b/src/Agent/AutopilotMonitor.Agent/Program.Configuration.cs
@@ -171,6 +171,24 @@ namespace AutopilotMonitor.Agent
                 catch { /* ignore corrupt file */ }
             }
 
+            // Await-enrollment config: if no --await-enrollment CLI arg, check for persisted config file.
+            // RunInstallMode persists await-enrollment.json so the Scheduled Task picks it up on restart.
+            var awaitConfigPath = Path.Combine(dataDirectory, "await-enrollment.json");
+            if (!awaitEnrollment && File.Exists(awaitConfigPath))
+            {
+                try
+                {
+                    var json = File.ReadAllText(awaitConfigPath);
+                    var awaitConfig = Newtonsoft.Json.JsonConvert.DeserializeObject<AwaitEnrollmentConfigFile>(json);
+                    if (awaitConfig != null)
+                    {
+                        awaitEnrollment = true;
+                        awaitEnrollmentTimeoutMinutes = awaitConfig.TimeoutMinutes;
+                    }
+                }
+                catch { /* ignore corrupt file */ }
+            }
+
             var useBootstrapToken = !string.IsNullOrEmpty(bootstrapToken);
 
             return new AgentConfiguration
diff --git a/src/Agent/AutopilotMonitor.Agent/Program.InstallMode.cs b/src/Agent/AutopilotMonitor.Agent/Program.InstallMode.cs
index e261dbd7..51112568 100644
--- a/src/Agent/AutopilotMonitor.Agent/Program.InstallMode.cs
+++ b/src/Agent/AutopilotMonitor.Agent/Program.InstallMode.cs
@@ -58,6 +58,22 @@ namespace AutopilotMonitor.Agent
                     logger.Info("Bootstrap config persisted for Scheduled Task");
                 }
 
+                // Persist await-enrollment config if --await-enrollment was provided.
+                // The Scheduled Task command line has no args, so the agent reads this file on restart.
+                if (args.Contains("--await-enrollment"))
+                {
+                    var dataDir = Environment.ExpandEnvironmentVariables(Constants.AgentDataDirectory);
+                    var awaitConfigPath = Path.Combine(dataDir, "await-enrollment.json");
+                    var awaitTimeoutArg = GetArgValue(args, "--await-enrollment-timeout");
+                    var timeoutMinutes = 480;
+                    if (!string.IsNullOrEmpty(awaitTimeoutArg) && int.TryParse(awaitTimeoutArg, out var parsed))
+                        timeoutMinutes = parsed;
+
+                    var awaitConfig = new AwaitEnrollmentConfigFile { TimeoutMinutes = timeoutMinutes };
+                    File.WriteAllText(awaitConfigPath, Newtonsoft.Json.JsonConvert.SerializeObject(awaitConfig));
+                    logger.Info($"Await-enrollment config persisted for Scheduled Task (timeout: {timeoutMinutes}min)");
+                }
+
                 var taskName = Constants.ScheduledTaskName;
                 var taskCommand = $"\"{targetExePath}\"";
 
diff --git a/src/Agent/AutopilotMonitor.Agent/Program.cs b/src/Agent/AutopilotMonitor.Agent/Program.cs
index 00d1453e..c21e8ae2 100644
--- a/src/Agent/AutopilotMonitor.Agent/Program.cs
+++ b/src/Agent/AutopilotMonitor.Agent/Program.cs
@@ -92,6 +92,7 @@ namespace AutopilotMonitor.Agent
 
                 logger.Info($"======================= Agent starting ({(consoleMode ? "console" : "background/SYSTEM")}) =======================");
                 logger.Info($"Agent version: {agentVersion}");
+                logger.Info($"Command line: {FormatArgsForLog(args)}");
 
                 // Check for enrollment complete marker (handles scheduled task cleanup retry)
                 if (CheckEnrollmentCompleteMarker(config, logger, consoleMode))
@@ -169,6 +170,23 @@ namespace AutopilotMonitor.Agent
                             logger.Warning("Await-enrollment: MDM certificate found but TenantId not yet in registry");
                         }
                     }
+
+                    // Remove persisted config so subsequent restarts proceed normally
+                    try
+                    {
+                        var awaitConfigPath = Path.Combine(
+                            Environment.ExpandEnvironmentVariables(Constants.AgentDataDirectory),
+                            "await-enrollment.json");
+                        if (File.Exists(awaitConfigPath))
+                        {
+                            File.Delete(awaitConfigPath);
+                            logger.Info("Await-enrollment: Config file removed — subsequent starts will proceed normally");
+                        }
+                    }
+                    catch (Exception ex)
+                    {
+                        logger.Warning($"Await-enrollment: Could not remove config file: {ex.Message}");
+                    }
                 }
 
                 using (var service = new MonitoringService(config, logger, agentVersion))
@@ -256,6 +274,23 @@ namespace AutopilotMonitor.Agent
             Console.WriteLine("  --replay-speed-factor <FACTOR>    Time compression factor (default: 50)");
         }
 
+        static string FormatArgsForLog(string[] args)
+        {
+            if (args == null || args.Length == 0)
+                return "(none)";
+
+            var parts = new string[args.Length];
+            for (int i = 0; i < args.Length; i++)
+            {
+                if (i > 0 && string.Equals(args[i - 1], "--bootstrap-token", StringComparison.OrdinalIgnoreCase))
+                    parts[i] = "***REDACTED***";
+                else
+                    parts[i] = args[i];
+            }
+
+            return string.Join(" ", parts);
+        }
+
         /// <summary>
         /// Checks if another AutopilotMonitor.Agent.exe process is already running.
         /// </summary>
@@ -287,4 +322,15 @@ namespace AutopilotMonitor.Agent
         public string BootstrapToken { get; set; }
         public string TenantId { get; set; }
     }
+
+    /// <summary>
+    /// Persisted await-enrollment configuration.
+    /// Saved to %ProgramData%\AutopilotMonitor\await-enrollment.json by RunInstallMode
+    /// so the Scheduled Task enters await-enrollment mode on startup.
+    /// Deleted after the MDM certificate is found.
+    /// </summary>
+    class AwaitEnrollmentConfigFile
+    {
+        public int TimeoutMinutes { get; set; } = 480;
+    }
 }
diff --git a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
index aeccadf7..2c60641d 100644
--- a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
+++ b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
@@ -1 +1 @@
-386
+388