diff --git a/pkg/webmiddleware/redirect.go b/pkg/webmiddleware/redirect.go
index 85e110a74b..52b4982737 100644
--- a/pkg/webmiddleware/redirect.go
+++ b/pkg/webmiddleware/redirect.go
@@ -54,6 +54,7 @@ func (c RedirectConfiguration) build(url *url.URL) (*url.URL, bool) {
 		if c.HostName != nil {
 			hostname = c.HostName(hostname)
 		}
+		originalPortStr := portStr
 		if c.Port != nil {
 			port, _ := strconv.ParseUint(portStr, 10, 0)
 			port = uint64(c.Port(uint(port)))
@@ -62,12 +63,15 @@ func (c RedirectConfiguration) build(url *url.URL) (*url.URL, bool) {
 		host := hostname
 		if portStr != "" {
 			switch {
-			case portStr == "0":
+			case portStr == "0" && originalPortStr == "":
 				// Just use the hostname.
+			case portStr == "0" && originalPortStr != "":
+				// Maintain the original port, in order to avoid loops.
+				host = net.JoinHostPort(host, originalPortStr)
 			case target.Scheme == "http" && portStr == "80":
-				// This is the default. Just use the hostame.
+				// This is the default. Just use the hostname.
 			case target.Scheme == "https" && portStr == "443":
-				// This is the default. Just use the hostame.
+				// This is the default. Just use the hostname.
 			default:
 				host = net.JoinHostPort(host, portStr)
 			}
diff --git a/pkg/webmiddleware/redirect_test.go b/pkg/webmiddleware/redirect_test.go
index d7ab61c620..60e14f2b11 100644
--- a/pkg/webmiddleware/redirect_test.go
+++ b/pkg/webmiddleware/redirect_test.go
@@ -27,6 +27,8 @@ import (
 )
 
 func TestRedirect(t *testing.T) {
+	t.Parallel()
+
 	m := Redirect(RedirectConfiguration{
 		Scheme: func(s string) string { return SchemeHTTPS },
 		HostName: func(h string) string {
@@ -47,6 +49,7 @@ func TestRedirect(t *testing.T) {
 	})
 
 	t.Run("None", func(t *testing.T) {
+		t.Parallel()
 		a := assertions.New(t)
 		r := httptest.NewRequest(http.MethodGet, "https://dev.example.com/path?query=true", nil)
 		rec := httptest.NewRecorder()
@@ -86,7 +89,9 @@ func TestRedirect(t *testing.T) {
 			Redirect: "https://dev.example.com/path",
 		},
 	} {
+		tc := tc
 		t.Run(tc.Name, func(t *testing.T) {
+			t.Parallel()
 			a := assertions.New(t)
 			r := httptest.NewRequest(http.MethodGet, tc.URL, nil)
 			rec := httptest.NewRecorder()
@@ -100,4 +105,19 @@ func TestRedirect(t *testing.T) {
 			a.So(res.Header.Get("Location"), should.Equal, tc.Redirect)
 		})
 	}
+
+	t.Run("ExplicitPort", func(t *testing.T) {
+		t.Parallel()
+		a := assertions.New(t)
+		r := httptest.NewRequest(http.MethodGet, "https://dev.example.com:8885/", nil)
+		rec := httptest.NewRecorder()
+		m(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			w.WriteHeader(http.StatusOK)
+			w.Write([]byte("OK"))
+		})).ServeHTTP(rec, r)
+		res := rec.Result()
+		a.So(res.StatusCode, should.Equal, http.StatusOK)
+		body, _ := io.ReadAll(res.Body)
+		a.So(string(body), should.Equal, "OK")
+	})
 }