diff --git a/hscontrol/types/config.go b/hscontrol/types/config.go
index fb720169..18fcd939 100644
--- a/hscontrol/types/config.go
+++ b/hscontrol/types/config.go
@@ -1301,23 +1301,11 @@ func isSafeServerURL(serverURL, baseDomain string) error {
 		return errServerURLSame
 	}
 
-	serverDomainParts := strings.Split(server.Host, ".")
-	baseDomainParts := strings.Split(baseDomain, ".")
-
-	if len(serverDomainParts) <= len(baseDomainParts) {
-		return nil
+	if strings.HasSuffix(server.Hostname(), "."+baseDomain) {
+		return errServerURLSuffix
 	}
 
-	s := len(serverDomainParts)
-
-	b := len(baseDomainParts)
-	for i := range baseDomainParts {
-		if serverDomainParts[s-i-1] != baseDomainParts[b-i-1] {
-			return nil
-		}
-	}
-
-	return errServerURLSuffix
+	return nil
 }
 
 type deprecator struct {
diff --git a/hscontrol/types/config_test.go b/hscontrol/types/config_test.go
index 8d7b286d..d9acf253 100644
--- a/hscontrol/types/config_test.go
+++ b/hscontrol/types/config_test.go
@@ -507,6 +507,47 @@ func TestSafeServerURL(t *testing.T) {
 	}
 }
 
+func TestSafeServerURLWithPort(t *testing.T) {
+	tests := []struct {
+		serverURL, baseDomain,
+		wantErr string
+	}{
+		{
+			serverURL:  "https://server.headscale.com:443",
+			baseDomain: "headscale.com",
+			wantErr:    errServerURLSuffix.Error(),
+		},
+		{
+			serverURL:  "https://server.subdomain.headscale.com:8080",
+			baseDomain: "headscale.com",
+			wantErr:    errServerURLSuffix.Error(),
+		},
+		{
+			serverURL:  "https://headscale.com:443",
+			baseDomain: "headscale.com",
+			wantErr:    errServerURLSame.Error(),
+		},
+		{
+			serverURL:  "https://example.com:8080",
+			baseDomain: "example.org",
+		},
+	}
+
+	for _, tt := range tests {
+		testName := fmt.Sprintf("server=%s domain=%s", tt.serverURL, tt.baseDomain)
+		t.Run(testName, func(t *testing.T) {
+			err := isSafeServerURL(tt.serverURL, tt.baseDomain)
+			if tt.wantErr != "" {
+				assert.EqualError(t, err, tt.wantErr)
+
+				return
+			}
+
+			assert.NoError(t, err)
+		})
+	}
+}
+
 // TestConfigJSONOmitsSecrets verifies that marshalling a [Config] to JSON
 // (as /debug/config does via [state.State.DebugConfig]) does not leak the
 // Postgres password, the OIDC client secret, or the headscale admin