diff --git a/allstarr/Controllers/JellyfinController.cs b/allstarr/Controllers/JellyfinController.cs
index 9fce43c..808c9c2 100644
--- a/allstarr/Controllers/JellyfinController.cs
+++ b/allstarr/Controllers/JellyfinController.cs
@@ -1789,7 +1789,22 @@ public class JellyfinController : ControllerBase
             var (deviceId, client, device, version) = ExtractDeviceInfo(Request.Headers);
             if (!string.IsNullOrEmpty(deviceId))
             {
-                await _sessionManager.EnsureSessionAsync(deviceId, client ?? "Unknown", device ?? "Unknown", version ?? "1.0", Request.Headers);
+                var sessionCreated = await _sessionManager.EnsureSessionAsync(deviceId, client ?? "Unknown", device ?? "Unknown", version ?? "1.0", Request.Headers);
+                if (sessionCreated)
+                {
+                    _logger.LogInformation("✓ Session ensured for device {DeviceId}", deviceId);
+                    
+                    // Give Jellyfin a moment to process the session creation
+                    await Task.Delay(100);
+                }
+                else
+                {
+                    _logger.LogWarning("⚠️ Failed to ensure session for device {DeviceId}", deviceId);
+                }
+            }
+            else
+            {
+                _logger.LogWarning("⚠️ No device ID found in headers - session cannot be created");
             }
 
             // Parse the body to check if it's an external track
diff --git a/allstarr/Services/Jellyfin/JellyfinSessionManager.cs b/allstarr/Services/Jellyfin/JellyfinSessionManager.cs
index 5fad725..3388d72 100644
--- a/allstarr/Services/Jellyfin/JellyfinSessionManager.cs
+++ b/allstarr/Services/Jellyfin/JellyfinSessionManager.cs
@@ -42,6 +42,9 @@ public class JellyfinSessionManager
         {
             existingSession.LastActivity = DateTime.UtcNow;
             _logger.LogDebug("Session already exists for device {DeviceId}", deviceId);
+            
+            // Refresh capabilities to keep session alive
+            await PostCapabilitiesAsync(headers);
             return true;
         }
 
@@ -50,45 +53,22 @@ public class JellyfinSessionManager
         try
         {
             // Post session capabilities to Jellyfin - this creates the session
-            var capabilities = new
+            await PostCapabilitiesAsync(headers);
+
+            _logger.LogInformation("✓ Session created for {DeviceId}", deviceId);
+
+            // Track this session
+            _sessions[deviceId] = new SessionInfo
             {
-                PlayableMediaTypes = new[] { "Audio" },
-                SupportedCommands = new[]
-                {
-                    "Play",
-                    "Playstate",
-                    "PlayNext"
-                },
-                SupportsMediaControl = true,
-                SupportsPersistentIdentifier = true,
-                SupportsSync = false
+                DeviceId = deviceId,
+                Client = client,
+                Device = device,
+                Version = version,
+                LastActivity = DateTime.UtcNow,
+                Headers = CloneHeaders(headers)
             };
 
-            var json = JsonSerializer.Serialize(capabilities);
-            var (result, statusCode) = await _proxyService.PostJsonAsync("Sessions/Capabilities/Full", json, headers);
-
-            if (statusCode == 204 || statusCode == 200)
-            {
-                _logger.LogInformation("✓ Session created for {DeviceId}", deviceId);
-
-                // Track this session
-                _sessions[deviceId] = new SessionInfo
-                {
-                    DeviceId = deviceId,
-                    Client = client,
-                    Device = device,
-                    Version = version,
-                    LastActivity = DateTime.UtcNow,
-                    Headers = CloneHeaders(headers)
-                };
-
-                return true;
-            }
-            else
-            {
-                _logger.LogWarning("Failed to create session for {DeviceId} - status {StatusCode}", deviceId, statusCode);
-                return false;
-            }
+            return true;
         }
         catch (Exception ex)
         {
@@ -97,6 +77,34 @@ public class JellyfinSessionManager
         }
     }
 
+    /// <summary>
+    /// Posts session capabilities to Jellyfin.
+    /// </summary>
+    private async Task PostCapabilitiesAsync(IHeaderDictionary headers)
+    {
+        var capabilities = new
+        {
+            PlayableMediaTypes = new[] { "Audio" },
+            SupportedCommands = new[]
+            {
+                "Play",
+                "Playstate",
+                "PlayNext"
+            },
+            SupportsMediaControl = true,
+            SupportsPersistentIdentifier = true,
+            SupportsSync = false
+        };
+
+        var json = JsonSerializer.Serialize(capabilities);
+        var (result, statusCode) = await _proxyService.PostJsonAsync("Sessions/Capabilities/Full", json, headers);
+
+        if (statusCode != 204 && statusCode != 200)
+        {
+            _logger.LogWarning("Failed to post capabilities - status {StatusCode}", statusCode);
+        }
+    }
+
     /// <summary>
     /// Updates session activity timestamp.
     /// </summary>
@@ -150,18 +158,7 @@ public class JellyfinSessionManager
             try
             {
                 // Post capabilities again to keep session alive
-                var capabilities = new
-                {
-                    PlayableMediaTypes = new[] { "Audio" },
-                    SupportedCommands = new[] { "Play", "Playstate", "PlayNext" },
-                    SupportsMediaControl = true,
-                    SupportsPersistentIdentifier = true,
-                    SupportsSync = false
-                };
-
-                var json = JsonSerializer.Serialize(capabilities);
-                await _proxyService.PostJsonAsync("Sessions/Capabilities/Full", json, session.Headers);
-
+                await PostCapabilitiesAsync(session.Headers);
                 _logger.LogDebug("✓ Kept session alive for {DeviceId}", session.DeviceId);
             }
             catch (Exception ex)