diff --git a/session/group.go b/session/group.go
index ab4825e22..1294cce32 100644
--- a/session/group.go
+++ b/session/group.go
@@ -7,6 +7,10 @@ import (
 	"github.com/pkg/errors"
 )
 
+// ErrNoActiveSessions is returned when a session group does not contain any
+// active session IDs.
+var ErrNoActiveSessions = errors.New("no active sessions")
+
 type Group interface {
 	SessionIterator() Iterator
 }
@@ -69,7 +73,7 @@ func (sm *Manager) Any(ctx context.Context, g Group, f func(context.Context, str
 			if lastErr != nil {
 				return lastErr
 			}
-			return errors.Errorf("no active sessions")
+			return errors.WithStack(ErrNoActiveSessions)
 		}
 
 		timeoutCtx, cancel := context.WithCancelCause(ctx)
diff --git a/util/resolver/authorizer.go b/util/resolver/authorizer.go
index da772460b..ced4b78fb 100644
--- a/util/resolver/authorizer.go
+++ b/util/resolver/authorizer.go
@@ -48,6 +48,7 @@ func newAuthHandlerNS(sm *session.Manager) *authHandlerNS {
 }
 
 func (a *authHandlerNS) get(ctx context.Context, host string, sm *session.Manager, g session.Group) *authFetcher {
+	hasSession := false
 	if g != nil {
 		if iter := g.SessionIterator(); iter != nil {
 			for {
@@ -55,6 +56,7 @@ func (a *authHandlerNS) get(ctx context.Context, host string, sm *session.Manage
 				if id == "" {
 					break
 				}
+				hasSession = true
 				h, ok := a.fetchers[host+"/"+id]
 				if ok {
 					h.lastUsed = time.Now()
@@ -64,6 +66,14 @@ func (a *authHandlerNS) get(ctx context.Context, host string, sm *session.Manage
 		}
 	}
 
+	if !hasSession {
+		h, ok := a.fetchers[host+"/"]
+		if ok {
+			h.lastUsed = time.Now()
+			return h
+		}
+	}
+
 	// link existing fetcher
 	for k, h := range a.fetchers {
 		parts := strings.SplitN(k, "/", 2)
@@ -186,12 +196,12 @@ func (a *dockerAuthorizer) AddResponses(ctx context.Context, responses []*http.R
 
 			var username, secret string
 			sessionID, pubKey, err := sessionauth.GetTokenAuthority(ctx, host, a.sm, a.session)
-			if err != nil {
+			if err != nil && !errors.Is(err, session.ErrNoActiveSessions) {
 				return err
 			}
 			if pubKey == nil {
 				sessionID, username, secret, err = a.getCredentials(ctx, host)
-				if err != nil {
+				if err != nil && !errors.Is(err, session.ErrNoActiveSessions) {
 					return err
 				}
 			}
diff --git a/util/resolver/authorizer_test.go b/util/resolver/authorizer_test.go
index d435209c7..3d4098613 100644
--- a/util/resolver/authorizer_test.go
+++ b/util/resolver/authorizer_test.go
@@ -1,8 +1,16 @@
 package resolver
 
 import (
+	"encoding/json"
+	"fmt"
+	"net/http"
+	"net/http/httptest"
 	"reflect"
 	"testing"
+	"time"
+
+	"github.com/moby/buildkit/session"
+	"github.com/stretchr/testify/require"
 )
 
 func TestParseScopes(t *testing.T) {
@@ -54,3 +62,59 @@ func TestParseScopes(t *testing.T) {
 		})
 	}
 }
+
+func TestBearerAuthFallsBackToAnonymousTokenWithoutSession(t *testing.T) {
+	type tokenRequest struct {
+		authorization string
+		service       string
+		scope         string
+	}
+	tokenRequests := make(chan tokenRequest, 1)
+	tokenServer := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		tokenRequests <- tokenRequest{
+			authorization: r.Header.Get("Authorization"),
+			service:       r.URL.Query().Get("service"),
+			scope:         r.URL.Query().Get("scope"),
+		}
+
+		w.Header().Set("Content-Type", "application/json")
+		if err := json.NewEncoder(w).Encode(map[string]any{
+			"token":      "anonymous-token",
+			"expires_in": 60,
+		}); err != nil {
+			t.Errorf("failed to write token response: %v", err)
+		}
+	}))
+	defer tokenServer.Close()
+
+	sm, err := session.NewManager()
+	require.NoError(t, err)
+
+	auth := newDockerAuthorizer(tokenServer.Client(), newAuthHandlerNS(sm), sm, session.NewGroup(""))
+
+	req := httptest.NewRequestWithContext(t.Context(), http.MethodGet, "https://registry.example/v2/library/alpine/manifests/latest", nil)
+	res := &http.Response{
+		StatusCode: http.StatusUnauthorized,
+		Header:     http.Header{},
+		Request:    req,
+	}
+	res.Header.Set("WWW-Authenticate", fmt.Sprintf(
+		`Bearer realm=%q,service="registry.example",scope="repository:library/alpine:pull"`,
+		tokenServer.URL+"/token",
+	))
+
+	require.NoError(t, auth.AddResponses(t.Context(), []*http.Response{res}))
+
+	retryReq := httptest.NewRequestWithContext(t.Context(), http.MethodGet, "https://registry.example/v2/library/alpine/manifests/latest", nil)
+	require.NoError(t, auth.Authorize(t.Context(), retryReq))
+	require.Equal(t, "Bearer anonymous-token", retryReq.Header.Get("Authorization"))
+
+	select {
+	case req := <-tokenRequests:
+		require.Empty(t, req.authorization)
+		require.Equal(t, "registry.example", req.service)
+		require.Equal(t, "repository:library/alpine:pull", req.scope)
+	case <-time.After(time.Second):
+		t.Fatal("expected anonymous token request")
+	}
+}