diff --git a/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/MonitoringService.cs b/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/MonitoringService.cs
index 69553477..45fa6108 100644
--- a/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/MonitoringService.cs
+++ b/src/Agent/AutopilotMonitor.Agent.Core/Monitoring/MonitoringService.cs
@@ -403,12 +403,20 @@ namespace AutopilotMonitor.Agent.Core.Monitoring
             }
 
             // Check for enrollment completion events
-            if (_configuration.SelfDestructOnComplete &&
-                (evt.EventType == "enrollment_complete" || evt.EventType == "enrollment_failed"))
+            if (evt.EventType == "enrollment_complete" || evt.EventType == "enrollment_failed")
             {
                 _logger.Info($"Enrollment completion detected: {evt.EventType}");
-                Task.Run(() => HandleEnrollmentComplete());
-                return; // Don't continue with normal event processing
+
+                // ALWAYS delete session ID when enrollment is complete/failed
+                // This ensures a new session will be created on next enrollment
+                DeleteSessionId();
+
+                // Only trigger self-destruct if configured
+                if (_configuration.SelfDestructOnComplete)
+                {
+                    Task.Run(() => HandleEnrollmentComplete());
+                    return; // Don't continue with normal event processing
+                }
             }
 
             // Immediate upload for:
@@ -499,6 +507,26 @@ namespace AutopilotMonitor.Agent.Core.Monitoring
             }
         }
 
+        /// <summary>
+        /// Deletes the persisted session ID file
+        /// Should be called when enrollment is complete/failed
+        /// </summary>
+        private void DeleteSessionId()
+        {
+            _logger.Info("Deleting persisted session ID...");
+            try
+            {
+                var dataDirectory = Environment.ExpandEnvironmentVariables(@"%ProgramData%\AutopilotMonitor");
+                var sessionPersistence = new SessionPersistence(dataDirectory);
+                sessionPersistence.DeleteSession();
+                _logger.Info("Session ID deleted successfully");
+            }
+            catch (Exception ex)
+            {
+                _logger.Warning($"Failed to delete session ID: {ex.Message}");
+            }
+        }
+
         /// <summary>
         /// Handles enrollment completion and triggers self-destruct sequence
         /// </summary>
@@ -520,7 +548,7 @@ namespace AutopilotMonitor.Agent.Core.Monitoring
                 // Give a moment for final upload to complete
                 await Task.Delay(2000);
 
-                // Step 3: Execute self-destruct
+                // Step 3: Execute self-destruct or cleanup
                 if (_configuration.SelfDestructOnComplete)
                 {
                     ExecuteSelfDestruct();
diff --git a/src/Agent/AutopilotMonitor.Agent.Core/Storage/SessionPersistence.cs b/src/Agent/AutopilotMonitor.Agent.Core/Storage/SessionPersistence.cs
new file mode 100644
index 00000000..4f4361bc
--- /dev/null
+++ b/src/Agent/AutopilotMonitor.Agent.Core/Storage/SessionPersistence.cs
@@ -0,0 +1,100 @@
+using System;
+using System.IO;
+
+namespace AutopilotMonitor.Agent.Core.Storage
+{
+    /// <summary>
+    /// Manages persistent session ID storage to maintain tracking across agent restarts
+    /// </summary>
+    public class SessionPersistence
+    {
+        private readonly string _sessionFilePath;
+        private readonly object _lockObject = new object();
+
+        public SessionPersistence(string dataDirectory)
+        {
+            if (string.IsNullOrWhiteSpace(dataDirectory))
+            {
+                throw new ArgumentNullException(nameof(dataDirectory));
+            }
+
+            if (!Directory.Exists(dataDirectory))
+            {
+                Directory.CreateDirectory(dataDirectory);
+            }
+
+            _sessionFilePath = Path.Combine(dataDirectory, "session.id");
+        }
+
+        /// <summary>
+        /// Loads existing session ID from disk or creates a new one if none exists
+        /// </summary>
+        /// <returns>Session ID (GUID string)</returns>
+        public string LoadOrCreateSessionId()
+        {
+            lock (_lockObject)
+            {
+                try
+                {
+                    // Check if session file exists and is valid
+                    if (File.Exists(_sessionFilePath))
+                    {
+                        var sessionId = File.ReadAllText(_sessionFilePath).Trim();
+
+                        // Validate it's a valid GUID format
+                        if (Guid.TryParse(sessionId, out _))
+                        {
+                            return sessionId;
+                        }
+                    }
+
+                    // Create new session ID if file doesn't exist or is invalid
+                    var newSessionId = Guid.NewGuid().ToString();
+                    File.WriteAllText(_sessionFilePath, newSessionId);
+                    return newSessionId;
+                }
+                catch (Exception ex)
+                {
+                    // If we can't read/write the session file, generate a new ID in memory
+                    // Log this error if logger is available
+                    throw new InvalidOperationException($"Failed to load or create session ID at {_sessionFilePath}", ex);
+                }
+            }
+        }
+
+        /// <summary>
+        /// Deletes the persisted session ID file
+        /// This should be called when enrollment is complete
+        /// </summary>
+        public void DeleteSession()
+        {
+            lock (_lockObject)
+            {
+                try
+                {
+                    if (File.Exists(_sessionFilePath))
+                    {
+                        File.Delete(_sessionFilePath);
+                    }
+                }
+                catch (Exception)
+                {
+                    // Suppress deletion errors - not critical if cleanup fails
+                    // The file will be overwritten on next start anyway
+                }
+            }
+        }
+
+        /// <summary>
+        /// Checks if a persisted session ID exists
+        /// </summary>
+        /// <returns>True if session file exists</returns>
+        public bool SessionExists()
+        {
+            lock (_lockObject)
+            {
+                return File.Exists(_sessionFilePath);
+            }
+        }
+    }
+}
diff --git a/src/Agent/AutopilotMonitor.Agent/AutopilotMonitorService.cs b/src/Agent/AutopilotMonitor.Agent/AutopilotMonitorService.cs
index 7a9aca97..0fbc1f0e 100644
--- a/src/Agent/AutopilotMonitor.Agent/AutopilotMonitorService.cs
+++ b/src/Agent/AutopilotMonitor.Agent/AutopilotMonitorService.cs
@@ -3,6 +3,7 @@ using System.ServiceProcess;
 using AutopilotMonitor.Agent.Core.Configuration;
 using AutopilotMonitor.Agent.Core.Logging;
 using AutopilotMonitor.Agent.Core.Monitoring;
+using AutopilotMonitor.Agent.Core.Storage;
 
 namespace AutopilotMonitor.Agent
 {
@@ -61,12 +62,15 @@ namespace AutopilotMonitor.Agent
 
         private AgentConfiguration LoadConfiguration()
         {
-            // TODO: Load from registry or config file
-            // For now, return a default configuration
+            // Load or create persisted session ID
+            var dataDirectory = Environment.ExpandEnvironmentVariables(@"%ProgramData%\AutopilotMonitor");
+            var sessionPersistence = new SessionPersistence(dataDirectory);
+            var sessionId = sessionPersistence.LoadOrCreateSessionId();
+
             return new AgentConfiguration
             {
                 ApiBaseUrl = Environment.GetEnvironmentVariable("AUTOPILOT_MONITOR_API") ?? "http://localhost:7071",
-                SessionId = Guid.NewGuid().ToString(),
+                SessionId = sessionId,
                 TenantId = "default-tenant",
                 SpoolDirectory = Environment.ExpandEnvironmentVariables(@"%ProgramData%\AutopilotMonitor\Spool"),
                 LogDirectory = Environment.ExpandEnvironmentVariables(@"%ProgramData%\AutopilotMonitor\Logs"),
diff --git a/src/Agent/AutopilotMonitor.Agent/Program.cs b/src/Agent/AutopilotMonitor.Agent/Program.cs
index 5a3a82f8..3a1536f4 100644
--- a/src/Agent/AutopilotMonitor.Agent/Program.cs
+++ b/src/Agent/AutopilotMonitor.Agent/Program.cs
@@ -6,6 +6,7 @@ using System.ServiceProcess;
 using AutopilotMonitor.Agent.Core.Configuration;
 using AutopilotMonitor.Agent.Core.Logging;
 using AutopilotMonitor.Agent.Core.Monitoring;
+using AutopilotMonitor.Agent.Core.Storage;
 using Microsoft.Win32;
 using Newtonsoft.Json;
 
@@ -264,10 +265,20 @@ namespace AutopilotMonitor.Agent
                 }
             }
 
+            // Load or create persisted session ID
+            var dataDirectory = Environment.ExpandEnvironmentVariables(@"%ProgramData%\AutopilotMonitor");
+            var sessionPersistence = new SessionPersistence(dataDirectory);
+            var sessionId = sessionPersistence.LoadOrCreateSessionId();
+
+            var sessionStatus = sessionPersistence.SessionExists() && File.GetCreationTime(Path.Combine(dataDirectory, "session.id")) < DateTime.Now.AddMinutes(-1)
+                ? "Restored from previous session"
+                : "New session created";
+            Console.WriteLine($"Session ID: {sessionId} ({sessionStatus})");
+
             return new AgentConfiguration
             {
                 ApiBaseUrl = apiBaseUrl,
-                SessionId = Guid.NewGuid().ToString(),
+                SessionId = sessionId,
                 TenantId = tenantId,
                 SpoolDirectory = Environment.ExpandEnvironmentVariables(@"%ProgramData%\AutopilotMonitor\Spool"),
                 LogDirectory = Environment.ExpandEnvironmentVariables(@"%ProgramData%\AutopilotMonitor\Logs"),