diff --git a/internal/db/queries.go b/internal/db/queries.go
index d6fbb91..5b209dd 100644
--- a/internal/db/queries.go
+++ b/internal/db/queries.go
@@ -869,6 +869,60 @@ func (database *Database) DeleteStaleUsers(
 	return deleted, nil
 }
 
+// StaleSession holds the id and nick of a session
+// whose clients are all stale.
+type StaleSession struct {
+	ID   int64
+	Nick string
+}
+
+// GetStaleOrphanSessions returns sessions where every
+// client has a last_seen before cutoff.
+func (database *Database) GetStaleOrphanSessions(
+	ctx context.Context,
+	cutoff time.Time,
+) ([]StaleSession, error) {
+	rows, err := database.conn.QueryContext(ctx,
+		`SELECT s.id, s.nick
+		 FROM sessions s
+		 WHERE s.id IN (
+		   SELECT DISTINCT session_id FROM clients
+		   WHERE last_seen < ?
+		 )
+		 AND s.id NOT IN (
+		   SELECT DISTINCT session_id FROM clients
+		   WHERE last_seen >= ?
+		 )`, cutoff, cutoff)
+	if err != nil {
+		return nil, fmt.Errorf(
+			"get stale orphan sessions: %w", err,
+		)
+	}
+
+	defer func() { _ = rows.Close() }()
+
+	var result []StaleSession
+
+	for rows.Next() {
+		var stale StaleSession
+		if err := rows.Scan(&stale.ID, &stale.Nick); err != nil {
+			return nil, fmt.Errorf(
+				"scan stale session: %w", err,
+			)
+		}
+
+		result = append(result, stale)
+	}
+
+	if err := rows.Err(); err != nil {
+		return nil, fmt.Errorf(
+			"iterate stale sessions: %w", err,
+		)
+	}
+
+	return result, nil
+}
+
 // GetSessionChannels returns channels a session
 // belongs to.
 func (database *Database) GetSessionChannels(
diff --git a/internal/handlers/api.go b/internal/handlers/api.go
index b963f9b..ad31dd3 100644
--- a/internal/handlers/api.go
+++ b/internal/handlers/api.go
@@ -1405,7 +1405,7 @@ func (hdlr *Handlers) HandleLogout() http.HandlerFunc {
 
 		if remaining == 0 {
 			hdlr.cleanupUser(
-				request, sessionID, nick,
+				ctx, sessionID, nick,
 			)
 		}
 
@@ -1418,12 +1418,10 @@ func (hdlr *Handlers) HandleLogout() http.HandlerFunc {
 // cleanupUser parts the user from all channels (notifying
 // members) and deletes the session.
 func (hdlr *Handlers) cleanupUser(
-	request *http.Request,
+	ctx context.Context,
 	sessionID int64,
 	nick string,
 ) {
-	ctx := request.Context()
-
 	channels, _ := hdlr.params.Database.
 		GetSessionChannels(ctx, sessionID)
 
diff --git a/internal/handlers/handlers.go b/internal/handlers/handlers.go
index 7ce952e..ed6ef04 100644
--- a/internal/handlers/handlers.go
+++ b/internal/handlers/handlers.go
@@ -169,6 +169,20 @@ func (hdlr *Handlers) runCleanup(
 ) {
 	cutoff := time.Now().Add(-timeout)
 
+	// Find sessions that will be orphaned so we can send
+	// QUIT notifications before deleting anything.
+	stale, err := hdlr.params.Database.
+		GetStaleOrphanSessions(ctx, cutoff)
+	if err != nil {
+		hdlr.log.Error(
+			"stale session lookup failed", "error", err,
+		)
+	}
+
+	for _, ss := range stale {
+		hdlr.cleanupUser(ctx, ss.ID, ss.Nick)
+	}
+
 	deleted, err := hdlr.params.Database.DeleteStaleUsers(
 		ctx, cutoff,
 	)