diff --git a/allstarr/Controllers/JellyfinController.cs b/allstarr/Controllers/JellyfinController.cs
index 37f91b7..70c8a77 100644
--- a/allstarr/Controllers/JellyfinController.cs
+++ b/allstarr/Controllers/JellyfinController.cs
@@ -1731,6 +1731,7 @@ public class JellyfinController : ControllerBase
     /// <summary>
     /// Reports playback start. Handles both local and external tracks.
     /// For local tracks, forwards to Jellyfin. For external tracks, logs locally.
+    /// Also ensures session is initialized if this is the first report from a device.
     /// </summary>
     [HttpPost("Sessions/Playing")]
     public async Task<IActionResult> ReportPlaybackStart()
@@ -1749,6 +1750,50 @@ public class JellyfinController : ControllerBase
             _logger.LogInformation("Auth headers: {Headers}", 
                 string.Join(", ", Request.Headers.Where(h => h.Key.Contains("Auth", StringComparison.OrdinalIgnoreCase)).Select(h => $"{h.Key}={h.Value}")));
 
+            // Extract device info from auth headers for session initialization
+            string? deviceId = null;
+            string? client = null;
+            string? device = null;
+            string? version = null;
+            
+            if (Request.Headers.TryGetValue("Authorization", out var authHeader))
+            {
+                var authStr = authHeader.ToString();
+                // Parse: MediaBrowser Client="...", Device="...", DeviceId="...", Version="..."
+                var parts = authStr.Replace("MediaBrowser ", "").Split(',');
+                foreach (var part in parts)
+                {
+                    var kv = part.Trim().Split('=');
+                    if (kv.Length == 2)
+                    {
+                        var key = kv[0].Trim();
+                        var value = kv[1].Trim('"');
+                        if (key == "DeviceId") deviceId = value;
+                        else if (key == "Client") client = value;
+                        else if (key == "Device") device = value;
+                        else if (key == "Version") version = value;
+                    }
+                }
+            }
+
+            // Ensure session capabilities are posted to Jellyfin (if not already done)
+            if (!string.IsNullOrEmpty(deviceId))
+            {
+                _logger.LogInformation("🔧 Ensuring session exists for device: {DeviceId} ({Client} {Version})", deviceId, client, version);
+                
+                // Post capabilities to ensure session is created
+                var capabilitiesEndpoint = $"Sessions/Capabilities?playableMediaTypes=Audio&supportedCommands=&supportsMediaControl=false&supportsPersistentIdentifier=true";
+                try
+                {
+                    var (capResult, capStatus) = await _proxyService.PostJsonAsync(capabilitiesEndpoint, "{}", Request.Headers);
+                    _logger.LogInformation("✓ Session capabilities posted ({StatusCode})", capStatus);
+                }
+                catch (Exception ex)
+                {
+                    _logger.LogWarning(ex, "Failed to post session capabilities, continuing anyway");
+                }
+            }
+
             // Parse the body to check if it's an external track
             var doc = JsonDocument.Parse(body);
             string? itemId = null;
@@ -1945,6 +1990,60 @@ public class JellyfinController : ControllerBase
         }
     }
 
+    /// <summary>
+    /// Catch-all for any other session-related requests.
+    /// This ensures all session management calls get proxied to Jellyfin.
+    /// </summary>
+    [HttpGet("Sessions/{**path}")]
+    [HttpPost("Sessions/{**path}")]
+    [HttpPut("Sessions/{**path}")]
+    [HttpDelete("Sessions/{**path}")]
+    public async Task<IActionResult> ProxySessionRequest(string path)
+    {
+        try
+        {
+            var method = Request.Method;
+            var queryString = Request.QueryString.HasValue ? Request.QueryString.Value : "";
+            var endpoint = $"Sessions/{path}{queryString}";
+            
+            _logger.LogInformation("🔄 Proxying session request: {Method} {Endpoint}", method, endpoint);
+            
+            // Read body if present
+            string body = "{}";
+            if ((method == "POST" || method == "PUT") && Request.ContentLength > 0)
+            {
+                Request.EnableBuffering();
+                using (var reader = new StreamReader(Request.Body, System.Text.Encoding.UTF8, detectEncodingFromByteOrderMarks: false, bufferSize: 1024, leaveOpen: true))
+                {
+                    body = await reader.ReadToEndAsync();
+                }
+                Request.Body.Position = 0;
+            }
+            
+            // Forward to Jellyfin
+            var (result, statusCode) = method switch
+            {
+                "GET" => await _proxyService.GetJsonAsync(endpoint, null, Request.Headers),
+                "POST" => await _proxyService.PostJsonAsync(endpoint, body, Request.Headers),
+                "PUT" => await _proxyService.PostJsonAsync(endpoint, body, Request.Headers), // Use POST for PUT
+                "DELETE" => await _proxyService.PostJsonAsync(endpoint, body, Request.Headers), // Use POST for DELETE
+                _ => (null, 405)
+            };
+            
+            if (result != null)
+            {
+                return new JsonResult(result.RootElement.Clone());
+            }
+            
+            return StatusCode(statusCode);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Failed to proxy session request");
+            return StatusCode(500);
+        }
+    }
+
     #endregion // Session Management
 
     #endregion // Playback Session Reporting
@@ -1989,8 +2088,16 @@ public class JellyfinController : ControllerBase
     [HttpPost("{**path}", Order = 100)]
     public async Task<IActionResult> ProxyRequest(string path)
     {
-        // DEBUG: Log EVERY request to see what's happening
-        _logger.LogWarning("ProxyRequest called with path: {Path}", path);
+        // Log session-related requests prominently to debug missing capabilities call
+        if (path.Contains("session", StringComparison.OrdinalIgnoreCase) || 
+            path.Contains("capabilit", StringComparison.OrdinalIgnoreCase))
+        {
+            _logger.LogWarning("🔍 SESSION/CAPABILITY REQUEST: {Method} /{Path}{Query}", Request.Method, path, Request.QueryString);
+        }
+        else
+        {
+            _logger.LogDebug("ProxyRequest: {Method} /{Path}", Request.Method, path);
+        }
         
         // Log endpoint usage to file for analysis
         await LogEndpointUsageAsync(path, Request.Method);
@@ -2216,7 +2323,8 @@ public class JellyfinController : ControllerBase
                 result = await UpdateSpotifyPlaylistCounts(result);
             }
 
-            return new JsonResult(JsonSerializer.Deserialize<object>(result.RootElement.GetRawText()));
+            // Return the raw JSON element directly to avoid deserialization issues with simple types
+            return new JsonResult(result.RootElement.Clone());
         }
         catch (Exception ex)
         {