diff --git a/CHANGELOG.md b/CHANGELOG.md
index a0150e526a4..11fe8f064d2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,7 @@ This project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.htm
 
 - The error received by `otelecho` middleware is then passed back to upstream middleware instead of being swallowed. (#3656)
 - Prevent taking from reservoir in AWS XRay Remote Sampler when there is zero capacity in `go.opentelemetry.io/contrib/samplers/aws/xray`. (#3684)
+- Fix `otelhttp.Handler` in `go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp` to propagate multiple `WriteHeader` calls while persisting the initial `statusCode`. (#3580)
 
 ## [1.16.0-rc.2/0.41.0-rc.2/0.10.0-rc.2] - 2023-03-23
 
diff --git a/instrumentation/net/http/otelhttp/test/handler_test.go b/instrumentation/net/http/otelhttp/test/handler_test.go
index 1ca75649d15..bb32935c176 100644
--- a/instrumentation/net/http/otelhttp/test/handler_test.go
+++ b/instrumentation/net/http/otelhttp/test/handler_test.go
@@ -178,6 +178,16 @@ func TestHandlerEmittedAttributes(t *testing.T) {
 				attribute.Int("http.status_code", http.StatusOK),
 			},
 		},
+		{
+			name: "With persisting initial failing status in handler with multiple WriteHeader calls",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusInternalServerError)
+				w.WriteHeader(http.StatusOK)
+			},
+			attributes: []attribute.KeyValue{
+				attribute.Int("http.status_code", http.StatusInternalServerError),
+			},
+		},
 	}
 	for _, tc := range testCases {
 		t.Run(tc.name, func(t *testing.T) {
@@ -201,6 +211,72 @@ func TestHandlerEmittedAttributes(t *testing.T) {
 	}
 }
 
+type respWriteHeaderCounter struct {
+	http.ResponseWriter
+
+	headersWritten []int
+}
+
+func (rw *respWriteHeaderCounter) WriteHeader(statusCode int) {
+	rw.headersWritten = append(rw.headersWritten, statusCode)
+	rw.ResponseWriter.WriteHeader(statusCode)
+}
+
+func TestHandlerPropagateWriteHeaderCalls(t *testing.T) {
+	testCases := []struct {
+		name                 string
+		handler              func(http.ResponseWriter, *http.Request)
+		expectHeadersWritten []int
+	}{
+		{
+			name: "With a success handler",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusOK)
+			},
+			expectHeadersWritten: []int{http.StatusOK},
+		},
+		{
+			name: "With a failing handler",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusBadRequest)
+			},
+			expectHeadersWritten: []int{http.StatusBadRequest},
+		},
+		{
+			name: "With an empty handler",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+			},
+
+			expectHeadersWritten: nil,
+		},
+		{
+			name: "With calling WriteHeader twice",
+			handler: func(w http.ResponseWriter, r *http.Request) {
+				w.WriteHeader(http.StatusInternalServerError)
+				w.WriteHeader(http.StatusOK)
+			},
+			expectHeadersWritten: []int{http.StatusInternalServerError, http.StatusOK},
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			sr := tracetest.NewSpanRecorder()
+			provider := sdktrace.NewTracerProvider()
+			provider.RegisterSpanProcessor(sr)
+			h := otelhttp.NewHandler(
+				http.HandlerFunc(tc.handler), "test_handler",
+				otelhttp.WithTracerProvider(provider),
+			)
+
+			recorder := httptest.NewRecorder()
+			rw := &respWriteHeaderCounter{ResponseWriter: recorder}
+			h.ServeHTTP(rw, httptest.NewRequest("GET", "/", nil))
+			require.EqualValues(t, tc.expectHeadersWritten, rw.headersWritten, "should propagate all WriteHeader calls to underlying ResponseWriter")
+		})
+	}
+}
+
 func TestHandlerRequestWithTraceContext(t *testing.T) {
 	rr := httptest.NewRecorder()
 
diff --git a/instrumentation/net/http/otelhttp/wrap.go b/instrumentation/net/http/otelhttp/wrap.go
index da6468c4e59..11a35ed167f 100644
--- a/instrumentation/net/http/otelhttp/wrap.go
+++ b/instrumentation/net/http/otelhttp/wrap.go
@@ -50,7 +50,7 @@ func (w *bodyWrapper) Close() error {
 var _ http.ResponseWriter = &respWriterWrapper{}
 
 // respWriterWrapper wraps a http.ResponseWriter in order to track the number of
-// bytes written, the last error, and to catch the returned statusCode
+// bytes written, the last error, and to catch the first written statusCode.
 // TODO: The wrapped http.ResponseWriter doesn't implement any of the optional
 // types (http.Hijacker, http.Pusher, http.CloseNotifier, http.Flusher, etc)
 // that may be useful when using it in real life situations.
@@ -85,11 +85,15 @@ func (w *respWriterWrapper) Write(p []byte) (int, error) {
 	return n, err
 }
 
+// WriteHeader persists initial statusCode for span attribution.
+// All calls to WriteHeader will be propagated to the underlying ResponseWriter
+// and will persist the statusCode from the first call.
+// Blocking consecutive calls to WriteHeader alters expected behavior and will
+// remove warning logs from net/http where developers will notice incorrect handler implementations.
 func (w *respWriterWrapper) WriteHeader(statusCode int) {
-	if w.wroteHeader {
-		return
+	if !w.wroteHeader {
+		w.wroteHeader = true
+		w.statusCode = statusCode
 	}
-	w.wroteHeader = true
-	w.statusCode = statusCode
 	w.ResponseWriter.WriteHeader(statusCode)
 }