diff --git a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/HttpClient/HttpMessageHandlerCommon.cs b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/HttpClient/HttpMessageHandlerCommon.cs
index 68b4a9a47983..7ae19148500b 100644
--- a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/HttpClient/HttpMessageHandlerCommon.cs
+++ b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/HttpClient/HttpMessageHandlerCommon.cs
@@ -46,6 +46,10 @@ public static CallTargetState OnMethodBegin<TTarget, TRequest>(TTarget instance,
                     return new CallTargetState(scope);
                 }
             }
+            else
+            {
+                headers.Remove(HttpHeaderNames.TracingEnabled);
+            }
 
             return CallTargetState.GetDefault();
         }
diff --git a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/WebRequest/WebRequestCommon.cs b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/WebRequest/WebRequestCommon.cs
index 49fa23817f76..5e5ac74cec9e 100644
--- a/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/WebRequest/WebRequestCommon.cs
+++ b/tracer/src/Datadog.Trace/ClrProfiler/AutoInstrumentation/Http/WebRequest/WebRequestCommon.cs
@@ -41,7 +41,12 @@ public static CallTargetState GetRequestStream_OnMethodBegin<TTarget>(TTarget in
         /// <returns>Returns <c>true</c> if injection was performed, and <c>/false</c> otherwise</returns>
         public static bool TryInjectHeaders<TTarget>(TTarget instance)
         {
-            if (instance is HttpWebRequest request && IsTracingEnabled(request))
+            if (instance is not HttpWebRequest request)
+            {
+                return false;
+            }
+
+            if (IsTracingEnabled(request))
             {
                 var tracer = Tracer.Instance;
 
@@ -74,6 +79,8 @@ public static bool TryInjectHeaders<TTarget>(TTarget instance)
                 }
             }
 
+            request.Headers.Remove(HttpHeaderNames.TracingEnabled);
+
             return false;
         }