diff --git a/pkg/appview/db/oauth_store.go b/pkg/appview/db/oauth_store.go
index 3997f6a..40aa8f9 100644
--- a/pkg/appview/db/oauth_store.go
+++ b/pkg/appview/db/oauth_store.go
@@ -337,6 +337,103 @@ func scopesMatch(stored, desired []string) bool {
 	return true
 }
 
+// GetSessionStats returns statistics about stored OAuth sessions
+// Useful for monitoring and debugging session health
+func (s *OAuthStore) GetSessionStats(ctx context.Context) (map[string]interface{}, error) {
+	stats := make(map[string]interface{})
+
+	// Total sessions
+	var totalSessions int
+	err := s.db.QueryRowContext(ctx, `SELECT COUNT(*) FROM oauth_sessions`).Scan(&totalSessions)
+	if err != nil {
+		return nil, fmt.Errorf("failed to count sessions: %w", err)
+	}
+	stats["total_sessions"] = totalSessions
+
+	// Sessions by age
+	var sessionsOlderThan1Hour, sessionsOlderThan1Day, sessionsOlderThan7Days int
+
+	err = s.db.QueryRowContext(ctx, `
+		SELECT COUNT(*) FROM oauth_sessions
+		WHERE updated_at < datetime('now', '-1 hour')
+	`).Scan(&sessionsOlderThan1Hour)
+	if err == nil {
+		stats["sessions_idle_1h+"] = sessionsOlderThan1Hour
+	}
+
+	err = s.db.QueryRowContext(ctx, `
+		SELECT COUNT(*) FROM oauth_sessions
+		WHERE updated_at < datetime('now', '-1 day')
+	`).Scan(&sessionsOlderThan1Day)
+	if err == nil {
+		stats["sessions_idle_1d+"] = sessionsOlderThan1Day
+	}
+
+	err = s.db.QueryRowContext(ctx, `
+		SELECT COUNT(*) FROM oauth_sessions
+		WHERE updated_at < datetime('now', '-7 days')
+	`).Scan(&sessionsOlderThan7Days)
+	if err == nil {
+		stats["sessions_idle_7d+"] = sessionsOlderThan7Days
+	}
+
+	// Recent sessions (updated in last 5 minutes)
+	var recentSessions int
+	err = s.db.QueryRowContext(ctx, `
+		SELECT COUNT(*) FROM oauth_sessions
+		WHERE updated_at > datetime('now', '-5 minutes')
+	`).Scan(&recentSessions)
+	if err == nil {
+		stats["sessions_active_5m"] = recentSessions
+	}
+
+	return stats, nil
+}
+
+// ListSessionsForMonitoring returns a list of all sessions with basic info for monitoring
+// Returns: DID, session age (minutes), last update time
+func (s *OAuthStore) ListSessionsForMonitoring(ctx context.Context) ([]map[string]interface{}, error) {
+	rows, err := s.db.QueryContext(ctx, `
+		SELECT
+			account_did,
+			session_id,
+			created_at,
+			updated_at,
+			CAST((julianday('now') - julianday(updated_at)) * 24 * 60 AS INTEGER) as idle_minutes
+		FROM oauth_sessions
+		ORDER BY updated_at DESC
+	`)
+	if err != nil {
+		return nil, fmt.Errorf("failed to query sessions: %w", err)
+	}
+	defer rows.Close()
+
+	var sessions []map[string]interface{}
+	for rows.Next() {
+		var did, sessionID, createdAt, updatedAt string
+		var idleMinutes int
+
+		if err := rows.Scan(&did, &sessionID, &createdAt, &updatedAt, &idleMinutes); err != nil {
+			slog.Warn("Failed to scan session row", "error", err)
+			continue
+		}
+
+		sessions = append(sessions, map[string]interface{}{
+			"did":          did,
+			"session_id":   sessionID,
+			"created_at":   createdAt,
+			"updated_at":   updatedAt,
+			"idle_minutes": idleMinutes,
+		})
+	}
+
+	if err := rows.Err(); err != nil {
+		return nil, fmt.Errorf("error iterating sessions: %w", err)
+	}
+
+	return sessions, nil
+}
+
 // makeSessionKey creates a composite key for session storage
 func makeSessionKey(did, sessionID string) string {
 	return fmt.Sprintf("%s:%s", did, sessionID)
diff --git a/pkg/appview/middleware/registry.go b/pkg/appview/middleware/registry.go
index 535b195..1ece9ea 100644
--- a/pkg/appview/middleware/registry.go
+++ b/pkg/appview/middleware/registry.go
@@ -167,9 +167,21 @@ func (nr *NamespaceResolver) Repository(ctx context.Context, name reference.Name
 		var err error
 		serviceToken, err = token.GetOrFetchServiceToken(ctx, nr.refresher, did, holdDID, pdsEndpoint)
 		if err != nil {
-			slog.Error("Failed to get service token", "component", "registry/middleware", "did", did, "error", err)
-			slog.Error("User needs to re-authenticate via credential helper", "component", "registry/middleware")
-			return nil, nr.authErrorMessage("OAuth session expired")
+			slog.Error("Failed to get service token",
+				"component", "registry/middleware",
+				"did", did,
+				"holdDID", holdDID,
+				"pdsEndpoint", pdsEndpoint,
+				"error", err)
+
+			// Check if this is likely an OAuth session expiration
+			errMsg := err.Error()
+			if strings.Contains(errMsg, "OAuth session") || strings.Contains(errMsg, "OAuth validation") {
+				return nil, nr.authErrorMessage("OAuth session expired or invalidated by PDS. Your session has been cleared")
+			}
+
+			// Generic service token error
+			return nil, nr.authErrorMessage(fmt.Sprintf("Failed to obtain storage credentials: %v", err))
 		}
 	}
 
diff --git a/pkg/auth/oauth/client.go b/pkg/auth/oauth/client.go
index 5f0150a..4d2f819 100644
--- a/pkg/auth/oauth/client.go
+++ b/pkg/auth/oauth/client.go
@@ -231,3 +231,53 @@ func (r *Refresher) resumeSession(ctx context.Context, did string) (*oauth.Clien
 	}
 	return session, nil
 }
+
+// DeleteSession removes an OAuth session from storage and optionally invalidates the UI session
+// This is called when OAuth authentication fails to force re-authentication
+func (r *Refresher) DeleteSession(ctx context.Context, did string) error {
+	// Parse DID
+	accountDID, err := syntax.ParseDID(did)
+	if err != nil {
+		return fmt.Errorf("failed to parse DID: %w", err)
+	}
+
+	// Get the session ID before deleting (for logging)
+	type sessionGetter interface {
+		GetLatestSessionForDID(ctx context.Context, did string) (*oauth.ClientSessionData, string, error)
+	}
+
+	getter, ok := r.clientApp.Store.(sessionGetter)
+	if !ok {
+		return fmt.Errorf("store must implement GetLatestSessionForDID")
+	}
+
+	_, sessionID, err := getter.GetLatestSessionForDID(ctx, did)
+	if err != nil {
+		// No session to delete - this is fine
+		slog.Debug("No OAuth session to delete", "did", did)
+		return nil
+	}
+
+	// Delete OAuth session from database
+	if err := r.clientApp.Store.DeleteSession(ctx, accountDID, sessionID); err != nil {
+		slog.Warn("Failed to delete OAuth session", "did", did, "sessionID", sessionID, "error", err)
+		return fmt.Errorf("failed to delete OAuth session: %w", err)
+	}
+
+	slog.Info("Deleted stale OAuth session",
+		"component", "oauth/refresher",
+		"did", did,
+		"sessionID", sessionID,
+		"reason", "OAuth authentication failed")
+
+	// Also invalidate the UI session if store is configured
+	if r.uiSessionStore != nil {
+		r.uiSessionStore.DeleteByDID(did)
+		slog.Info("Invalidated UI session for DID",
+			"component", "oauth/refresher",
+			"did", did,
+			"reason", "OAuth session deleted")
+	}
+
+	return nil
+}
diff --git a/pkg/auth/token/servicetoken.go b/pkg/auth/token/servicetoken.go
index 334a10b..d53b226 100644
--- a/pkg/auth/token/servicetoken.go
+++ b/pkg/auth/token/servicetoken.go
@@ -48,6 +48,23 @@ func GetOrFetchServiceToken(
 	if err != nil {
 		// OAuth session unavailable - fail
 		InvalidateServiceToken(did, holdDID)
+		slog.Error("Failed to get OAuth session for service token",
+			"component", "token/servicetoken",
+			"did", did,
+			"holdDID", holdDID,
+			"pdsEndpoint", pdsEndpoint,
+			"error", err,
+			"errorType", fmt.Sprintf("%T", err))
+
+		// Delete the stale OAuth session to force re-authentication
+		// This also invalidates the UI session automatically
+		if delErr := refresher.DeleteSession(ctx, did); delErr != nil {
+			slog.Warn("Failed to delete stale OAuth session",
+				"component", "token/servicetoken",
+				"did", did,
+				"error", delErr)
+		}
+
 		return "", fmt.Errorf("failed to get OAuth session: %w", err)
 	}
 
@@ -74,6 +91,25 @@ func GetOrFetchServiceToken(
 	if err != nil {
 		// Auth error - may indicate expired tokens or corrupted session
 		InvalidateServiceToken(did, holdDID)
+		slog.Error("OAuth authentication failed during service token request",
+			"component", "token/servicetoken",
+			"did", did,
+			"holdDID", holdDID,
+			"pdsEndpoint", pdsEndpoint,
+			"url", serviceAuthURL,
+			"error", err,
+			"errorType", fmt.Sprintf("%T", err),
+			"hint", "This likely means the PDS rejected the OAuth session - refresh token may be expired or invalidated")
+
+		// Delete the stale OAuth session to force re-authentication
+		// This also invalidates the UI session automatically
+		if delErr := refresher.DeleteSession(ctx, did); delErr != nil {
+			slog.Warn("Failed to delete stale OAuth session",
+				"component", "token/servicetoken",
+				"did", did,
+				"error", delErr)
+		}
+
 		return "", fmt.Errorf("OAuth validation failed: %w", err)
 	}
 	defer resp.Body.Close()
@@ -82,6 +118,14 @@ func GetOrFetchServiceToken(
 		// Service auth failed
 		bodyBytes, _ := io.ReadAll(resp.Body)
 		InvalidateServiceToken(did, holdDID)
+		slog.Error("Service token request returned non-200 status",
+			"component", "token/servicetoken",
+			"did", did,
+			"holdDID", holdDID,
+			"pdsEndpoint", pdsEndpoint,
+			"statusCode", resp.StatusCode,
+			"responseBody", string(bodyBytes),
+			"hint", "PDS rejected the service token request - check PDS logs for details")
 		return "", fmt.Errorf("service auth failed with status %d: %s", resp.StatusCode, string(bodyBytes))
 	}