fix(quota): honor trialing as Pro + surface desktop-limit errors to the user

api/pkg/quota/quota.go

@@ -7,7 +7,6 @@ import (
 	external_agent "github.com/helixml/helix/api/pkg/external-agent"
 	"github.com/helixml/helix/api/pkg/store"
 	"github.com/helixml/helix/api/pkg/types"
-	"github.com/stripe/stripe-go/v76"
 )
 
 type QuotaManager interface {
@@ -61,7 +60,7 @@ func (m *DefaultQuotaManager) getOrgQuotas(ctx context.Context, orgID string) (*
 			MaxSpecTasks:          -1,
 		}
 	// Active subscription
-	case wallet.StripeSubscriptionID != "" && wallet.SubscriptionStatus == stripe.SubscriptionStatusActive:
+	case wallet.StripeSubscriptionID != "" && wallet.IsSubscriptionActive():
 		// Paid plan limits
 		quotas = m.getProQuotas()
 	default:
@@ -131,7 +130,7 @@ func (m *DefaultQuotaManager) getUserQuotas(ctx context.Context, userID string)
 			MaxRepositories:       -1,
 			MaxSpecTasks:          -1,
 		}
-	case wallet.StripeSubscriptionID != "" && wallet.SubscriptionStatus == stripe.SubscriptionStatusActive:
+	case wallet.StripeSubscriptionID != "" && wallet.IsSubscriptionActive():
 		// Paid plan limits
 		quotas = m.getProQuotas()
 	default:

api/pkg/quota/quota_test.go

@@ -87,6 +87,14 @@ func proWallet(userID string) *types.Wallet {
 	}
 }
 
+func trialingWallet(userID string) *types.Wallet {
+	return &types.Wallet{
+		UserID:               userID,
+		StripeSubscriptionID: "sub_trial",
+		SubscriptionStatus:   stripe.SubscriptionStatusTrialing,
+	}
+}
+
 func orgFreeWallet(orgID string) *types.Wallet {
 	return &types.Wallet{OrgID: orgID}
 }
@@ -140,6 +148,19 @@ func (s *QuotaManagerSuite) TestGetQuotas_UserProQuotas() {
 	s.Equal(10000, resp.MaxSpecTasks)
 }
 
+// A trialing subscription must grant Pro quotas, not Free. Regression test for
+// the bug where the quota path checked `status == active` exactly, so trialing
+// orgs were silently throttled to Free limits (e.g. 2 concurrent desktops).
+func (s *QuotaManagerSuite) TestGetQuotas_UserTrialingGetsProQuotas() {
+	s.expectUserQuotaDefaults("user1", trialingWallet("user1"), enforceQuotasSettings())
+
+	resp, err := s.manager.GetQuotas(context.Background(), &types.QuotaRequest{UserID: "user1"})
+	s.NoError(err)
+
+	s.Equal(5, resp.MaxConcurrentDesktops, "trialing should get Pro desktop limit, not Free")
+	s.Equal(20, resp.MaxProjects)
+}
+
 func (s *QuotaManagerSuite) TestGetQuotas_UserQuotasDisabled() {
 	s.expectUserQuotaDefaults("user1", freeWallet("user1"), disabledQuotasSettings())
 

api/pkg/server/auto_wake_stuck_interactions.go

@@ -691,6 +691,36 @@ func (apiServer *HelixAPIServer) maybeKickColdStart(ctx context.Context, stuck *
 		session = nil
 	}
 
+	// A desktop-quota block is NOT a transient cold-start — retrying can't help,
+	// and the generic "agent never connected" banner hides the real reason. If
+	// the session's org is at its concurrent-desktop limit (and quotas are
+	// enforced), surface the actual limit to the user immediately and stop.
+	// Mirrors hydra_executor.checkLimits (gated on EnforceQuotas).
+	if session != nil && apiServer.quotaManager != nil {
+		if settings, sErr := apiServer.Store.GetSystemSettings(ctx); sErr == nil && settings.EnforceQuotas {
+			if resp, qErr := apiServer.quotaManager.LimitReached(ctx, &types.QuotaLimitReachedRequest{
+				UserID:         session.Owner,
+				OrganizationID: session.OrganizationID,
+				Resource:       types.ResourceDesktop,
+			}); qErr == nil && resp != nil && resp.LimitReached {
+				stuck.State = types.InteractionStateError
+				stuck.Error = fmt.Sprintf("Desktop limit reached (%d). Stop a running desktop session, or raise your organization's concurrent-desktop limit, then retry.", resp.Limit)
+				stuck.Updated = time.Now()
+				stuck.Completed = time.Now()
+				if _, uErr := apiServer.Store.UpdateInteraction(ctx, stuck); uErr != nil {
+					log.Warn().Err(uErr).Str("interaction_id", stuck.ID).Msg("[AUTO_WAKE] Failed to mark interaction errored for desktop limit")
+					return
+				}
+				if _, clearErr := apiServer.Store.ClearSessionStartingStatus(ctx, stuck.SessionID); clearErr != nil {
+					log.Warn().Err(clearErr).Str("session_id", stuck.SessionID).Msg("[AUTO_WAKE] Failed to clear starting status after surfacing desktop limit")
+				}
+				log.Warn().Str("interaction_id", stuck.ID).Str("session_id", stuck.SessionID).Int("limit", resp.Limit).
+					Msg("[AUTO_WAKE] Desktop limit reached — surfaced to user, not retrying cold-start")
+				return
+			}
+		}
+	}
+
 	// Skip if a container boot is genuinely in progress and we're still
 	// inside the grace period. Both "starting" and "running" count as
 	// in-progress here: see the function header for why the post-bridge,

frontend/src/components/dashboard/ActivateTrialDialog.tsx

@@ -92,7 +92,7 @@ const ActivateTrialDialog: FC<ActivateTrialDialogProps> = ({ open, onClose, user
                 }}
             >
                 <Typography variant="h6" component="div">
-                    Activate Trial
+                    Activate
                 </Typography>
                 <IconButton aria-label="close" onClick={handleClose} disabled={activateTrial.isPending}>
                     <CloseIcon />
@@ -146,7 +146,7 @@ const ActivateTrialDialog: FC<ActivateTrialDialogProps> = ({ open, onClose, user
                     disabled={activateTrial.isPending}
                     startIcon={activateTrial.isPending ? <CircularProgress size={20} /> : null}
                 >
-                    {activateTrial.isPending ? 'Activating…' : 'Activate Trial'}
+                    {activateTrial.isPending ? 'Activating…' : 'Activate'}
                 </Button>
             </DialogActions>
         </Dialog>

frontend/src/components/dashboard/UsersTable.tsx

@@ -468,7 +468,7 @@ const UsersTable: FC<UsersTableProps> = ({ onSelectUser }) => {
                 {isCloud && !trialActiveOrStashed(menuUser) && (
                     <MenuItem onClick={handleActivateTrial}>
                         <ListItemIcon><CardGiftcardIcon fontSize="small" /></ListItemIcon>
-                        <ListItemText>Activate trial</ListItemText>
+                        <ListItemText>Activate</ListItemText>
                     </MenuItem>
                 )}
                 {isCloud && trialActiveOrStashed(menuUser) && (