diff --git a/src/OpenTelemetry.Instrumentation.Http/CHANGELOG.md b/src/OpenTelemetry.Instrumentation.Http/CHANGELOG.md
index d3158da9348..1aa38220666 100644
--- a/src/OpenTelemetry.Instrumentation.Http/CHANGELOG.md
+++ b/src/OpenTelemetry.Instrumentation.Http/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+* In case of .NET Core, additional spans created during retries will now be
+exported.
+([[#3729](https://github.com/open-telemetry/opentelemetry-dotnet/issues/3729)])
+
 ## 1.0.0-rc9.7
 
 Released 2022-Sep-29
diff --git a/src/OpenTelemetry.Instrumentation.Http/HttpRequestMessageContextPropagation.cs b/src/OpenTelemetry.Instrumentation.Http/HttpRequestMessageContextPropagation.cs
index 16999593811..14b26850e97 100644
--- a/src/OpenTelemetry.Instrumentation.Http/HttpRequestMessageContextPropagation.cs
+++ b/src/OpenTelemetry.Instrumentation.Http/HttpRequestMessageContextPropagation.cs
@@ -34,6 +34,7 @@ internal static class HttpRequestMessageContextPropagation
 
         internal static Action<HttpRequestMessage, string, string> HeaderValueSetter => (request, name, value) =>
         {
+            request.Headers.Remove(name);
             request.Headers.Add(name, value);
         };
     }
diff --git a/src/OpenTelemetry.Instrumentation.Http/Implementation/HttpHandlerDiagnosticListener.cs b/src/OpenTelemetry.Instrumentation.Http/Implementation/HttpHandlerDiagnosticListener.cs
index 2b1e741906d..7b066c0c755 100644
--- a/src/OpenTelemetry.Instrumentation.Http/Implementation/HttpHandlerDiagnosticListener.cs
+++ b/src/OpenTelemetry.Instrumentation.Http/Implementation/HttpHandlerDiagnosticListener.cs
@@ -115,14 +115,6 @@ public void OnStartActivity(Activity activity, object payload)
                 return;
             }
 
-            // TODO: Investigate why this check is needed.
-            if (Propagators.DefaultTextMapPropagator.Extract(default, request, HttpRequestMessageContextPropagation.HeaderValuesGetter) != default)
-            {
-                // this request is already instrumented, we should back off
-                activity.IsAllDataRequested = false;
-                return;
-            }
-
             // Propagate context irrespective of sampling decision
             var textMapPropagator = Propagators.DefaultTextMapPropagator;
             if (textMapPropagator is not TraceContextPropagator)
diff --git a/test/OpenTelemetry.Instrumentation.Http.Tests/HttpClientTests.Basic.cs b/test/OpenTelemetry.Instrumentation.Http.Tests/HttpClientTests.Basic.cs
index df742c63634..8d7581e49fe 100644
--- a/test/OpenTelemetry.Instrumentation.Http.Tests/HttpClientTests.Basic.cs
+++ b/test/OpenTelemetry.Instrumentation.Http.Tests/HttpClientTests.Basic.cs
@@ -301,7 +301,7 @@ public async Task HttpClientInstrumentation_AddViaFactory_HttpInstrumentation_Co
             Assert.IsType<Activity>(processor.Invocations[1].Arguments[0]);
         }
 
-        [Fact(Skip = "https://github.com/open-telemetry/opentelemetry-dotnet/issues/3729")]
+        [Fact]
         public async Task HttpClientInstrumentationExportsSpansCreatedForRetries()
         {
             var exportedItems = new List<Activity>();
@@ -321,7 +321,7 @@ public async Task HttpClientInstrumentationExportsSpansCreatedForRetries()
             await c.SendAsync(request);
 
             // number of exported spans should be 3(maxRetries)
-            Assert.Equal(3, exportedItems.Count());
+            Assert.Equal(maxRetries, exportedItems.Count());
 
             var spanid1 = exportedItems[0].SpanId;
             var spanid2 = exportedItems[1].SpanId;