diff --git a/hscontrol/handlers.go b/hscontrol/handlers.go
index 717934bf0..a4c981a22 100644
--- a/hscontrol/handlers.go
+++ b/hscontrol/handlers.go
@@ -8,7 +8,6 @@ import (
 	"io"
 	"net/http"
 	"strconv"
-	"strings"
 	"time"
 
 	"github.com/juanfont/headscale/hscontrol/assets"
@@ -305,14 +304,9 @@ func NewAuthProviderWeb(serverURL string) *AuthProviderWeb {
 }
 
 // authPathURL builds an auth-flow URL of the form
-// "<serverURL>/<kind>/<id>", trimming a trailing slash from serverURL.
+// "<serverURL>/<kind>/<id>".
 func authPathURL(serverURL, kind string, authID types.AuthID) string {
-	return fmt.Sprintf(
-		"%s/%s/%s",
-		strings.TrimSuffix(serverURL, "/"),
-		kind,
-		authID.String(),
-	)
+	return fmt.Sprintf("%s/%s/%s", serverURL, kind, authID.String())
 }
 
 func (a *AuthProviderWeb) RegisterURL(authID types.AuthID) string {
diff --git a/hscontrol/oidc.go b/hscontrol/oidc.go
index 62f8c6cc2..fa763b448 100644
--- a/hscontrol/oidc.go
+++ b/hscontrol/oidc.go
@@ -133,7 +133,7 @@ func (a *AuthProviderOIDC) cookiesSecure() bool {
 }
 
 func oidcCallbackURL(serverURL string) string {
-	return strings.TrimSuffix(serverURL, "/") + "/oidc/callback"
+	return serverURL + "/oidc/callback"
 }
 
 func (a *AuthProviderOIDC) oidcCallbackPath() string {
diff --git a/hscontrol/types/config.go b/hscontrol/types/config.go
index d93007e34..f105d2eca 100644
--- a/hscontrol/types/config.go
+++ b/hscontrol/types/config.go
@@ -1661,7 +1661,7 @@ func LoadServerConfig() (*Config, error) {
 		}
 	}
 
-	serverURL := viper.GetString("server_url")
+	serverURL := strings.TrimRight(viper.GetString("server_url"), "/")
 
 	// BaseDomain cannot be the same as the server URL.
 	// This is because Tailscale takes over the domain in BaseDomain,
diff --git a/hscontrol/types/config_test.go b/hscontrol/types/config_test.go
index a5f1d2202..507649f69 100644
--- a/hscontrol/types/config_test.go
+++ b/hscontrol/types/config_test.go
@@ -817,6 +817,38 @@ dns:
 	}
 }
 
+func TestServerURLTrailingSlash(t *testing.T) {
+	tests := []struct {
+		name  string
+		input string
+		want  string
+	}{
+		{name: "no slash", input: "https://h", want: "https://h"},
+		{name: "one slash", input: "https://h/", want: "https://h"},
+		{name: "two slashes", input: "https://h//", want: "https://h"},
+		{name: "port", input: "https://h:8443/", want: "https://h:8443"},
+		{name: "path prefix", input: "https://h/hs/", want: "https://h/hs"},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			viper.Reset()
+			t.Cleanup(viper.Reset)
+			require.NoError(t, LoadConfig("testdata/minimal.yaml", true))
+
+			viper.Set("server_url", tt.input)
+			viper.Set("prefixes.v4", "100.64.0.0/10")
+			viper.Set("database.type", "sqlite3")
+			viper.Set("dns.magic_dns", false)
+			viper.Set("dns.override_local_dns", false)
+
+			cfg, err := LoadServerConfig()
+			require.NoError(t, err)
+			assert.Equal(t, tt.want, cfg.ServerURL)
+		})
+	}
+}
+
 // OK
 // server_url: headscale.com, base: clients.headscale.com
 // server_url: headscale.com, base: headscale.net