diff --git a/internal/security/proxy/service.go b/internal/security/proxy/service.go
index af9547b19b..f19025f5c4 100644
--- a/internal/security/proxy/service.go
+++ b/internal/security/proxy/service.go
@@ -319,11 +319,11 @@ func (s *Service) postCert(cp bootstrapConfig.CertKeyPair) *CertError {
 	}
 	tokens := []string{s.configuration.KongURL.GetProxyBaseURL(), CertificatesPath}
 	req, err := http.NewRequest(http.MethodPost, strings.Join(tokens, "/"), strings.NewReader(string(data)))
-	req.Header.Add(common.ContentType, common.ContentTypeJSON)
 	if err != nil {
 		s.loggingClient.Errorf("failed to create upload cert request -- %s", err.Error())
 		return &CertError{err.Error(), InternalError}
 	}
+	req.Header.Add(common.ContentType, common.ContentTypeJSON)
 	resp, err := s.client.Do(req)
 	if err != nil {
 		s.loggingClient.Errorf("failed to upload cert to proxy server with error %s", err.Error())
diff --git a/internal/security/proxy/service_test.go b/internal/security/proxy/service_test.go
index 1108dee5ca..8ba4be59cd 100644
--- a/internal/security/proxy/service_test.go
+++ b/internal/security/proxy/service_test.go
@@ -87,6 +87,34 @@ func TestPostCertExists(t *testing.T) {
 	}
 }
 
+func TestPostCertHttpError(t *testing.T) {
+	fileName := "./testdata/configuration.toml"
+	contents, err := os.ReadFile(fileName)
+	require.NoError(t, err)
+
+	configuration := &config.ConfigurationStruct{}
+	err = toml.Unmarshal(contents, configuration)
+	require.NoError(t, err)
+
+	ts := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}))
+	defer ts.Close()
+
+	// Setting a mal-formatted hostname and port to force error.
+	configuration.KongURL = config.KongUrlInfo{
+		Server:          "{}",
+		ApplicationPort: -1,
+	}
+
+	mockLogger := logger.MockLogger{}
+	service := NewService(NewRequestor(true, 10, "", mockLogger), mockLogger, configuration)
+	mockCertPair := bootstrapConfig.CertKeyPair{Cert: "test-certificate", Key: "test-private-key"}
+	e := service.postCert(mockCertPair)
+	require.Error(t, e)
+	if e.reason != CertExisting {
+		assert.Contains(t, e.Error(), "/admin/certificates")
+	}
+}
+
 func TestInit(t *testing.T) {
 	fileName := "./testdata/configuration.toml"
 	contents, err := os.ReadFile(fileName)