diff --git a/access_gate.go b/access_gate.go
index 29cf92b..586ccab 100644
--- a/access_gate.go
+++ b/access_gate.go
@@ -81,8 +81,9 @@ func (g *AccessGate) Check(r *http.Request) CheckResult {
 }
 
 func (g *AccessGate) memberOfRequired(userID string) (bool, error) {
+	key := g.cacheKey(userID)
 	if g.CacheTTL > 0 {
-		if g.cachedAllowed(userID) {
+		if g.cachedAllowed(key) {
 			return true, nil
 		}
 	}
@@ -94,7 +95,7 @@ func (g *AccessGate) memberOfRequired(userID string) (bool, error) {
 		for _, have := range groups {
 			if have == need {
 				if g.CacheTTL > 0 {
-					g.storeAllowed(userID)
+					g.storeAllowed(key)
 				}
 				return true, nil
 			}
@@ -103,6 +104,10 @@ func (g *AccessGate) memberOfRequired(userID string) (bool, error) {
 	return false, nil
 }
 
+func (g *AccessGate) cacheKey(userID string) string {
+	return userID + "\x00" + strings.Join(g.Groups, "\x00")
+}
+
 func (g *AccessGate) fetchUserGroups(userID string) ([]string, error) {
 	ocs := g.ocsClient(userID)
 	path := "cloud/users/" + url.PathEscape(userID) + "/groups"
@@ -139,24 +144,24 @@ func decodeUserGroups(raw []byte) ([]string, error) {
 	return parsed.OCS.Data.Groups, nil
 }
 
-func (g *AccessGate) cachedAllowed(userID string) bool {
+func (g *AccessGate) cachedAllowed(key string) bool {
 	g.mu.Lock()
 	defer g.mu.Unlock()
-	ent, ok := g.cache[userID]
+	ent, ok := g.cache[key]
 	if !ok {
 		return false
 	}
 	if g.Now().After(ent.until) {
-		delete(g.cache, userID)
+		delete(g.cache, key)
 		return false
 	}
 	return true
 }
 
-func (g *AccessGate) storeAllowed(userID string) {
+func (g *AccessGate) storeAllowed(key string) {
 	g.mu.Lock()
 	defer g.mu.Unlock()
-	g.cache[userID] = cacheEntry{until: g.Now().Add(g.CacheTTL)}
+	g.cache[key] = cacheEntry{until: g.Now().Add(g.CacheTTL)}
 }
 
 func (g AccessGate) normalized() *AccessGate {
@@ -185,27 +190,28 @@ func acceptsHTML(accept string) bool {
 }
 
 func (g *AccessGate) shouldSkip(path string) bool {
-	path = strings.TrimSuffix(path, "/")
-	if path == "" {
-		path = "/"
-	}
+	path = normalizeGatePath(path)
 	for _, p := range defaultSkipPaths {
 		if path == p {
 			return true
 		}
 	}
 	for _, p := range g.ExtraSkipPaths {
-		p = strings.TrimSuffix(p, "/")
-		if p == "" {
-			p = "/"
-		}
-		if path == p {
+		if path == normalizeGatePath(p) {
 			return true
 		}
 	}
 	return false
 }
 
+func normalizeGatePath(path string) string {
+	path = strings.TrimSuffix(path, "/")
+	if path == "" {
+		return "/"
+	}
+	return path
+}
+
 var defaultSkipPaths = []string{"/heartbeat", "/enabled", "/init"}
 
 var deniedHTML = []byte(`<!DOCTYPE html>
diff --git a/access_gate_test.go b/access_gate_test.go
index e12aea3..f098151 100644
--- a/access_gate_test.go
+++ b/access_gate_test.go
@@ -213,6 +213,35 @@ func TestAccessGateCachesPositiveMembership(t *testing.T) {
 	}
 }
 
+func TestAccessGateCacheKeyedByGroupSet(t *testing.T) {
+	var calls atomic.Int32
+	srv := groupsOCSServer(t, func(w http.ResponseWriter, r *http.Request) {
+		calls.Add(1)
+		_ = json.NewEncoder(w).Encode(map[string]any{
+			"ocs": map[string]any{"data": map[string]any{"groups": []string{"dns-ops"}}},
+		})
+	})
+	cred := gonexapp.Credentials{
+		BaseURL: srv.URL, AppID: "app", AppVersion: "0.1.0", AAVersion: "1.0.0", AppSecret: "s",
+	}
+	gate := &gonexapp.AccessGate{
+		Cred: cred, Groups: []string{"dns-ops"}, CacheTTL: time.Minute,
+		Client: srv.Client(), OCS: gonexapp.OCSClient{Cred: cred, Client: srv.Client()},
+	}
+	req := httptest.NewRequest(http.MethodGet, "/api/zones", nil)
+	req.Header.Set("AUTHORIZATION-APP-API", authHeader("alice"))
+	if gate.Check(req) != gonexapp.CheckAllowed {
+		t.Fatal("first allow")
+	}
+	gate.Groups = []string{"other-group"}
+	if gate.Check(req) != gonexapp.CheckDenied {
+		t.Fatalf("after group-set change want denied, calls=%d", calls.Load())
+	}
+	if calls.Load() != 2 {
+		t.Fatalf("ocs calls=%d want 2 (cache must not reuse prior group-set)", calls.Load())
+	}
+}
+
 func TestAccessGateDoesNotCacheDenial(t *testing.T) {
 	var calls atomic.Int32
 	srv := groupsOCSServer(t, func(w http.ResponseWriter, r *http.Request) {