fix monitor desktop unknown recovery

server/internal/tenant/app/monitoring_callback_service.go

@@ -945,6 +945,7 @@ func (s *MonitoringCallbackService) skipTaskForInstallation(
 	}
 
 	skipReason := normalizeSkipReason(req.SkipReason)
+	skipOutcome := monitoringSkipOutcomeForReason(skipReason)
 
 	tx, err := s.monitoringPool.Begin(ctx)
 	if err != nil {
@@ -954,14 +955,14 @@ func (s *MonitoringCallbackService) skipTaskForInstallation(
 
 	if _, err := tx.Exec(ctx, `
 		UPDATE monitoring_collect_tasks
-		SET status = 'skipped',
+		SET status = $2,
 		    callback_received_at = NOW(),
-		    completed_at = $2,
-		    skip_reason = $3,
-		    error_message = $4,
+		    completed_at = $3,
+		    skip_reason = $4,
+		    error_message = $5,
 		    updated_at = NOW()
 		WHERE id = $1
-	`, task.ID, completedAt, skipReason, nullableString(req.ErrorMessage)); err != nil {
+	`, task.ID, skipOutcome.TaskStatus, completedAt, nullableStringPtr(skipOutcome.StoredSkipReason), nullableString(req.ErrorMessage)); err != nil {
 		return nil, response.ErrInternal(50041, "task_update_failed", "failed to update monitoring task skip status")
 	}
 
@@ -978,12 +979,34 @@ func (s *MonitoringCallbackService) skipTaskForInstallation(
 	completedAtText := completedAt.Format(time.RFC3339)
 	return &MonitoringSkipTaskResponse{
 		TaskID:      task.ID,
-		TaskStatus:  "skipped",
+		TaskStatus:  skipOutcome.TaskStatus,
 		SkipReason:  skipReason,
 		CompletedAt: &completedAtText,
 	}, nil
 }
 
+type monitoringSkipOutcome struct {
+	TaskStatus       string
+	StoredSkipReason string
+}
+
+func monitoringSkipOutcomeForReason(skipReason string) monitoringSkipOutcome {
+	switch strings.TrimSpace(skipReason) {
+	case "runtime_unknown":
+		return monitoringSkipOutcome{TaskStatus: "failed"}
+	default:
+		return monitoringSkipOutcome{TaskStatus: "skipped", StoredSkipReason: strings.TrimSpace(skipReason)}
+	}
+}
+
+func nullableStringPtr(value string) *string {
+	trimmed := strings.TrimSpace(value)
+	if trimmed == "" {
+		return nil
+	}
+	return &trimmed
+}
+
 func (s *MonitoringCallbackService) CancelTaskForDesktopClient(
 	ctx context.Context,
 	client *repository.DesktopClient,
@@ -1504,7 +1527,7 @@ func (s *MonitoringCallbackService) loadActiveDesktopMonitorExecutionLease(
 		FROM desktop_tasks
 		WHERE kind = 'monitor'
 		  AND monitor_task_id = $1
-		  AND status IN ('queued', 'in_progress', 'unknown')
+		  AND status IN ('queued', 'in_progress')
 		ORDER BY created_at DESC, id DESC
 		LIMIT 1
 	`, monitorTaskID).Scan(
@@ -2349,16 +2372,7 @@ func (s *MonitoringCallbackService) completeLinkedDesktopMonitorTask(
 		workspaceID     int64
 		activeAttemptID pgtype.UUID
 	)
-	if err := tx.QueryRow(ctx, `
-		SELECT desktop_id, workspace_id, active_attempt_id
-		FROM desktop_tasks
-		WHERE kind = 'monitor'
-		  AND monitor_task_id = $1
-		  AND status IN ('in_progress', 'unknown')
-		ORDER BY created_at DESC, id DESC
-		LIMIT 1
-		FOR UPDATE
-	`, task.ID).Scan(&desktopID, &workspaceID, &activeAttemptID); err != nil {
+	if err := tx.QueryRow(ctx, completeLinkedDesktopMonitorTaskLookupSQL(), task.ID).Scan(&desktopID, &workspaceID, &activeAttemptID); err != nil {
 		if err == pgx.ErrNoRows {
 			return nil
 		}
@@ -2434,6 +2448,19 @@ func (s *MonitoringCallbackService) completeLinkedDesktopMonitorTask(
 	return nil
 }
 
+func completeLinkedDesktopMonitorTaskLookupSQL() string {
+	return `
+		SELECT desktop_id, workspace_id, active_attempt_id
+		FROM desktop_tasks
+		WHERE kind = 'monitor'
+		  AND monitor_task_id = $1
+		  AND status = 'in_progress'
+		ORDER BY created_at DESC, id DESC
+		LIMIT 1
+		FOR UPDATE
+	`
+}
+
 func (s *MonitoringCallbackService) replaceCitationFacts(ctx context.Context, tx pgx.Tx, tenantID, runID int64) error {
 	if _, err := tx.Exec(ctx, `
 		DELETE FROM monitoring_citation_facts