diff --git a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
index d4d7ff29..a3888f7a 100644
--- a/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
+++ b/src/Agent/AutopilotMonitor.Agent/buildcounter.txt
@@ -1 +1 @@
-685
+687
diff --git a/src/Backend/AutopilotMonitor.Functions/Middleware/AuthenticationMiddleware.cs b/src/Backend/AutopilotMonitor.Functions/Middleware/AuthenticationMiddleware.cs
index 4c051c3c..042bcfec 100644
--- a/src/Backend/AutopilotMonitor.Functions/Middleware/AuthenticationMiddleware.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Middleware/AuthenticationMiddleware.cs
@@ -10,6 +10,7 @@ using System.IdentityModel.Tokens.Jwt;
 using Microsoft.AspNetCore.Http;
 using System.Net;
 using System.Security.Claims;
+using AutopilotMonitor.Functions.Extensions;
 using AutopilotMonitor.Functions.Helpers;
 using AutopilotMonitor.Shared.DataAccess;
 
@@ -232,10 +233,9 @@ public class AuthenticationMiddleware : IFunctionsWorkerMiddleware
             authenticated = true;
 
             // Track per-user usage (fire-and-forget via Task.Run to ensure execution in isolated worker)
-            var oid = principal.FindFirst("oid")?.Value;
-            var upn = principal.FindFirst("upn")?.Value
-                   ?? principal.FindFirst("preferred_username")?.Value;
-            var tid = principal.FindFirst("tid")?.Value;
+            var oid = principal.GetObjectId();
+            var upn = principal.GetUserPrincipalName();
+            var tid = principal.GetTenantId();
             if (!string.IsNullOrEmpty(oid))
             {
                 var normalizedEndpoint = EndpointNormalizer.Normalize(requestPath);
diff --git a/src/Backend/AutopilotMonitor.Functions/Middleware/RequestTelemetryMiddleware.cs b/src/Backend/AutopilotMonitor.Functions/Middleware/RequestTelemetryMiddleware.cs
new file mode 100644
index 00000000..de1304f0
--- /dev/null
+++ b/src/Backend/AutopilotMonitor.Functions/Middleware/RequestTelemetryMiddleware.cs
@@ -0,0 +1,98 @@
+using System.Diagnostics;
+using Microsoft.ApplicationInsights;
+using Microsoft.ApplicationInsights.DataContracts;
+using Microsoft.Azure.Functions.Worker;
+using Microsoft.Azure.Functions.Worker.Middleware;
+using AutopilotMonitor.Functions.Helpers;
+
+namespace AutopilotMonitor.Functions.Middleware;
+
+/// <summary>
+/// Emits worker-side <see cref="RequestTelemetry"/> with business context (TenantId, UserId,
+/// CorrelationId, UserRole) so the Application Insights <c>requests</c> table is queryable
+/// by tenant, user, and correlation ID. Runs first in the pipeline to capture accurate
+/// duration including auth and policy evaluation. Non-HTTP triggers are skipped.
+/// </summary>
+public class RequestTelemetryMiddleware : IFunctionsWorkerMiddleware
+{
+    private readonly TelemetryClient _telemetryClient;
+
+    public RequestTelemetryMiddleware(TelemetryClient telemetryClient)
+    {
+        _telemetryClient = telemetryClient;
+    }
+
+    public async Task Invoke(FunctionContext context, FunctionExecutionDelegate next)
+    {
+        var httpContext = context.GetHttpContext();
+        if (httpContext == null)
+        {
+            // Non-HTTP trigger (timer, queue) — nothing to track
+            await next(context);
+            return;
+        }
+
+        var sw = Stopwatch.StartNew();
+        var startTime = DateTimeOffset.UtcNow;
+        Exception? caughtException = null;
+
+        try
+        {
+            await next(context);
+        }
+        catch (Exception ex)
+        {
+            caughtException = ex;
+            throw;
+        }
+        finally
+        {
+            sw.Stop();
+
+            var statusCode = caughtException != null ? 500 : httpContext.Response.StatusCode;
+            var functionName = context.FunctionDefinition.Name;
+            var method = httpContext.Request.Method;
+            var url = $"{httpContext.Request.Scheme}://{httpContext.Request.Host}{httpContext.Request.Path}{httpContext.Request.QueryString}";
+
+            var requestTelemetry = new RequestTelemetry
+            {
+                Name = $"{method} {functionName}",
+                Timestamp = startTime,
+                Duration = sw.Elapsed,
+                ResponseCode = statusCode.ToString(),
+                Success = statusCode < 500,
+                Url = new Uri(url),
+            };
+
+            // Distributed trace correlation
+            var activity = Activity.Current;
+            if (activity != null)
+            {
+                requestTelemetry.Context.Operation.Id = activity.RootId;
+                requestTelemetry.Context.Operation.ParentId = activity.Id;
+            }
+
+            // Business context from downstream middleware
+            requestTelemetry.Properties["Source"] = "WorkerMiddleware";
+            requestTelemetry.Properties["FunctionName"] = functionName;
+            requestTelemetry.Properties["HttpMethod"] = method;
+            requestTelemetry.Properties["HttpPath"] = httpContext.Request.Path.Value ?? "";
+
+            if (context.Items.TryGetValue("CorrelationId", out var corrId) && corrId is string correlationId)
+                requestTelemetry.Properties["CorrelationId"] = correlationId;
+
+            var reqCtx = context.GetRequestContext();
+            if (!string.IsNullOrEmpty(reqCtx.TenantId))
+                requestTelemetry.Properties["TenantId"] = reqCtx.TenantId;
+            if (!string.IsNullOrEmpty(reqCtx.UserPrincipalName))
+                requestTelemetry.Properties["UserId"] = reqCtx.UserPrincipalName;
+            if (!string.IsNullOrEmpty(reqCtx.UserRole))
+                requestTelemetry.Properties["UserRole"] = reqCtx.UserRole;
+
+            if (caughtException != null)
+                requestTelemetry.Properties["ExceptionType"] = caughtException.GetType().Name;
+
+            _telemetryClient.TrackRequest(requestTelemetry);
+        }
+    }
+}
diff --git a/src/Backend/AutopilotMonitor.Functions/Program.cs b/src/Backend/AutopilotMonitor.Functions/Program.cs
index 356a19fd..1c9062a7 100644
--- a/src/Backend/AutopilotMonitor.Functions/Program.cs
+++ b/src/Backend/AutopilotMonitor.Functions/Program.cs
@@ -21,7 +21,8 @@ var builder = FunctionsApplication.CreateBuilder(args);
 builder.ConfigureFunctionsWebApplication();
 
 // Register middleware pipeline (Azure Functions .NET 8 isolated worker pattern)
-// Order matters: correlation ID (all requests) → JWT authentication (401) → policy enforcement (403)
+// Order matters: request telemetry (wraps all) → correlation ID → JWT authentication (401) → policy enforcement (403)
+builder.UseMiddleware<RequestTelemetryMiddleware>();
 builder.UseMiddleware<CorrelationIdMiddleware>();
 builder.UseMiddleware<AuthenticationMiddleware>();
 builder.UseMiddleware<PolicyEnforcementMiddleware>();