diff --git a/WEB/Src/Web/Web/AccountIdActivityProcessor.cs b/WEB/Src/Web/Web/AccountIdActivityProcessor.cs
index 9b23c6b6f..e2786bb4f 100644
--- a/WEB/Src/Web/Web/AccountIdActivityProcessor.cs
+++ b/WEB/Src/Web/Web/AccountIdActivityProcessor.cs
@@ -33,7 +33,8 @@ public override void OnEnd(Activity activity)
             }
 
             var context = HttpContext.Current;
-            if (context == null)
+            var request = context.GetRequest();
+            if (request == null)
             {
                 return;
             }
@@ -42,7 +43,7 @@ public override void OnEnd(Activity activity)
             var existingAccountId = activity.GetTagItem("enduser.id");
             if (existingAccountId == null || string.IsNullOrEmpty(existingAccountId.ToString()))
             {
-                var authUserCookie = context.Request.UnvalidatedGetCookie(RequestTrackingConstants.WebAuthenticatedUserCookieName);
+                var authUserCookie = request.UnvalidatedGetCookie(RequestTrackingConstants.WebAuthenticatedUserCookieName);
                 if (authUserCookie != null && !string.IsNullOrEmpty(authUserCookie.Value))
                 {
                     var authUserCookieString = HttpUtility.UrlDecode(authUserCookie.Value);
diff --git a/WEB/Src/Web/Web/AuthenticatedUserIdActivityProcessor.cs b/WEB/Src/Web/Web/AuthenticatedUserIdActivityProcessor.cs
index d5118c688..f340cdc69 100644
--- a/WEB/Src/Web/Web/AuthenticatedUserIdActivityProcessor.cs
+++ b/WEB/Src/Web/Web/AuthenticatedUserIdActivityProcessor.cs
@@ -31,7 +31,8 @@ public override void OnEnd(Activity activity)
             }
 
             var context = HttpContext.Current;
-            if (context == null)
+            var request = context.GetRequest();
+            if (request == null)
             {
                 return;
             }
@@ -40,7 +41,7 @@ public override void OnEnd(Activity activity)
             var existingUserId = activity.GetTagItem("enduser.id");
             if (existingUserId == null || string.IsNullOrEmpty(existingUserId.ToString()))
             {
-                var authUserCookie = context.Request.UnvalidatedGetCookie(RequestTrackingConstants.WebAuthenticatedUserCookieName);
+                var authUserCookie = request.UnvalidatedGetCookie(RequestTrackingConstants.WebAuthenticatedUserCookieName);
                 if (authUserCookie != null && !string.IsNullOrEmpty(authUserCookie.Value))
                 {
                     var authUserCookieString = HttpUtility.UrlDecode(authUserCookie.Value);
diff --git a/WEB/Src/Web/Web/ClientIpHeaderActivityProcessor.cs b/WEB/Src/Web/Web/ClientIpHeaderActivityProcessor.cs
index 686bd7cc7..437bee5ca 100644
--- a/WEB/Src/Web/Web/ClientIpHeaderActivityProcessor.cs
+++ b/WEB/Src/Web/Web/ClientIpHeaderActivityProcessor.cs
@@ -77,7 +77,8 @@ public override void OnEnd(Activity activity)
             }
 
             var context = HttpContext.Current;
-            if (context == null)
+            var request = context.GetRequest();
+            if (request == null)
             {
                 return;
             }
@@ -90,10 +91,10 @@ public override void OnEnd(Activity activity)
                 foreach (var clientIpHeaderName in this.HeaderNames)
                 {
                     // Try Unvalidated first, fall back to regular Headers for test environments
-                    var clientIpsFromHeader = context.Request.UnvalidatedGetHeader(clientIpHeaderName);
+                    var clientIpsFromHeader = request.UnvalidatedGetHeader(clientIpHeaderName);
                     if (string.IsNullOrWhiteSpace(clientIpsFromHeader))
                     {
-                        clientIpsFromHeader = context.Request.Headers[clientIpHeaderName];
+                        clientIpsFromHeader = request.Headers[clientIpHeaderName];
                     }
 
                     if (!string.IsNullOrWhiteSpace(clientIpsFromHeader))
@@ -111,7 +112,7 @@ public override void OnEnd(Activity activity)
 
                 if (string.IsNullOrEmpty(resultIp))
                 {
-                    resultIp = context.Request.GetUserHostAddress();
+                    resultIp = request.GetUserHostAddress();
                 }
 
                 if (!string.IsNullOrEmpty(resultIp))
diff --git a/WEB/Src/Web/Web/Implementation/HttpContextExtensions.cs b/WEB/Src/Web/Web/Implementation/HttpContextExtensions.cs
index 5bb94c5a8..f0e921070 100644
--- a/WEB/Src/Web/Web/Implementation/HttpContextExtensions.cs
+++ b/WEB/Src/Web/Web/Implementation/HttpContextExtensions.cs
@@ -11,12 +11,28 @@ internal static class HttpContextExtensions
     {
         /// <summary>
         /// Gets the HttpRequest from the HttpContext.
+        /// Returns null if no request is available (e.g., when called outside of a
+        /// request context such as during <c>Application_Start</c>), in which case
+        /// <see cref="HttpContext.Request"/> throws <see cref="HttpException"/>.
         /// </summary>
         /// <param name="context">The HttpContext.</param>
-        /// <returns>The HttpRequest.</returns>
+        /// <returns>The HttpRequest, or null if not available.</returns>
         public static HttpRequest GetRequest(this HttpContext context)
         {
-            return context?.Request;
+            if (context == null)
+            {
+                return null;
+            }
+
+            try
+            {
+                return context.Request;
+            }
+            catch (HttpException)
+            {
+                // "Request is not available in this context" — e.g., Application_Start.
+                return null;
+            }
         }
 
         /// <summary>
@@ -26,12 +42,12 @@ public static HttpRequest GetRequest(this HttpContext context)
         /// <returns>The request name in format "VERB Controller/Action" or "VERB Path".</returns>
         public static string CreateRequestNamePrivate(this HttpContext context)
         {
-            if (context?.Request == null)
+            var request = context.GetRequest();
+            if (request == null)
             {
                 return string.Empty;
             }
 
-            var request = context.Request;
             string verb = request.HttpMethod ?? "GET";
             
             // Try to get controller and action from route data
diff --git a/WEB/Src/Web/Web/SessionActivityProcessor.cs b/WEB/Src/Web/Web/SessionActivityProcessor.cs
index 594d4d892..b067dce4f 100644
--- a/WEB/Src/Web/Web/SessionActivityProcessor.cs
+++ b/WEB/Src/Web/Web/SessionActivityProcessor.cs
@@ -35,7 +35,8 @@ public override void OnEnd(Activity activity)
             }
 
             var context = HttpContext.Current;
-            if (context == null)
+            var request = context.GetRequest();
+            if (request == null)
             {
                 return;
             }
@@ -45,7 +46,7 @@ public override void OnEnd(Activity activity)
             if (existingSessionId == null || string.IsNullOrEmpty(existingSessionId.ToString()))
             {
                 // Try Unvalidated first, fall back to regular Cookies for test environments
-                var sessionCookie = context.Request.UnvalidatedGetCookie(WebSessionCookieName) ?? context.Request.Cookies[WebSessionCookieName];
+                var sessionCookie = request.UnvalidatedGetCookie(WebSessionCookieName) ?? request.Cookies[WebSessionCookieName];
                 if (sessionCookie != null && !string.IsNullOrWhiteSpace(sessionCookie.Value))
                 {
                     var parts = sessionCookie.Value.Split('|');
diff --git a/WEB/Src/Web/Web/UserActivityProcessor.cs b/WEB/Src/Web/Web/UserActivityProcessor.cs
index c07853a7e..58bc86d27 100644
--- a/WEB/Src/Web/Web/UserActivityProcessor.cs
+++ b/WEB/Src/Web/Web/UserActivityProcessor.cs
@@ -33,7 +33,8 @@ public override void OnEnd(Activity activity)
             }
 
             var context = HttpContext.Current;
-            if (context == null)
+            var request = context.GetRequest();
+            if (request == null)
             {
                 return;
             }
@@ -43,7 +44,7 @@ public override void OnEnd(Activity activity)
             if (existingUserId == null || string.IsNullOrEmpty(existingUserId.ToString()))
             {
                 // Try Unvalidated first, fall back to regular Cookies for test environments
-                var userCookie = context.Request.UnvalidatedGetCookie(WebUserCookieName) ?? context.Request.Cookies[WebUserCookieName];
+                var userCookie = request.UnvalidatedGetCookie(WebUserCookieName) ?? request.Cookies[WebUserCookieName];
                 if (userCookie != null && !string.IsNullOrEmpty(userCookie.Value))
                 {
                     var cookieParts = userCookie.Value.Split('|');