diff --git a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs
index 80e7b86621cc..6a6d7137e0ec 100644
--- a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs
+++ b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Core.cs
@@ -168,8 +168,16 @@ internal override bool IsBlocked
 
         internal override bool ReportedExternalWafsRequestHeaders
         {
-            get => Context.Items["ReportedExternalWafsRequestHeaders"] is true;
-            set => Context.Items["ReportedExternalWafsRequestHeaders"] = value;
+            get
+            {
+                if (Context.Items.TryGetValue(ReportedExternalWafsRequestHeaders, out var value))
+                {
+                    return value is bool boolValue && boolValue;
+                }
+
+                return false;
+            }
+            set => Context.Items[ReportedExternalWafsRequestHeaders] = value;
         }
 
         internal override void MarkBlocked() => Context.Items[BlockingAction.BlockDefaultActionName] = true;
diff --git a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Framework.cs b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Framework.cs
index 288596dbf889..4dfc03766ce7 100644
--- a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Framework.cs
+++ b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.Framework.cs
@@ -536,8 +536,8 @@ public HttpTransport(HttpContext context)
 
         internal override bool ReportedExternalWafsRequestHeaders
         {
-            get => Context.Items["ReportedExternalWafsRequestHeaders"] is true;
-            set => Context.Items["ReportedExternalWafsRequestHeaders"] = value;
+            get => Context.Items[ReportedExternalWafsRequestHeaders] is true;
+            set => Context.Items[ReportedExternalWafsRequestHeaders] = value;
         }
 
         internal override void MarkBlocked() => Context.Items[BlockingAction.BlockDefaultActionName] = true;
diff --git a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.cs b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.cs
index d6b99284f91d..71c35cf8d362 100644
--- a/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.cs
+++ b/tracer/src/Datadog.Trace/AppSec/Coordinator/SecurityCoordinator.cs
@@ -27,6 +27,7 @@ namespace Datadog.Trace.AppSec.Coordinator;
 /// </summary>
 internal readonly partial struct SecurityCoordinator
 {
+    private const string ReportedExternalWafsRequestHeaders = "ReportedExternalWafsRequestHeaders";
     private static readonly IDatadogLogger Log = DatadogLogging.GetLoggerFor<SecurityCoordinator>();
     private readonly Security _security;
     private readonly Span _localRootSpan;