diff --git a/connector/dummy.go b/connector/dummy.go
index d991f2b1..3cd5a0d1 100644
--- a/connector/dummy.go
+++ b/connector/dummy.go
@@ -197,9 +197,11 @@ func (conn *Dummy) AddMessagesToMailbox(ctx context.Context, messageIDs []imap.M
 		conn.pushUpdate(imap.NewMessageMailboxesUpdated(
 			messageID,
 			conn.state.getMailboxIDs(messageID),
-			conn.state.isSeen(messageID),
-			conn.state.isFlagged(messageID),
-			conn.state.isDraft(messageID),
+			imap.MessageCustomFlags{
+				Seen:    conn.state.isSeen(messageID),
+				Flagged: conn.state.isFlagged(messageID),
+				Draft:   conn.state.isDraft(messageID),
+			},
 		))
 	}
 
@@ -213,9 +215,11 @@ func (conn *Dummy) RemoveMessagesFromMailbox(ctx context.Context, messageIDs []i
 		conn.pushUpdate(imap.NewMessageMailboxesUpdated(
 			messageID,
 			conn.state.getMailboxIDs(messageID),
-			conn.state.isSeen(messageID),
-			conn.state.isFlagged(messageID),
-			conn.state.isDraft(messageID),
+			imap.MessageCustomFlags{
+				Seen:    conn.state.isSeen(messageID),
+				Flagged: conn.state.isFlagged(messageID),
+				Draft:   conn.state.isDraft(messageID),
+			},
 		))
 	}
 
@@ -230,9 +234,11 @@ func (conn *Dummy) MoveMessages(ctx context.Context, messageIDs []imap.MessageID
 		conn.pushUpdate(imap.NewMessageMailboxesUpdated(
 			messageID,
 			conn.state.getMailboxIDs(messageID),
-			conn.state.isSeen(messageID),
-			conn.state.isFlagged(messageID),
-			conn.state.isDraft(messageID),
+			imap.MessageCustomFlags{
+				Seen:    conn.state.isSeen(messageID),
+				Flagged: conn.state.isFlagged(messageID),
+				Draft:   conn.state.isDraft(messageID),
+			},
 		))
 	}
 
@@ -245,9 +251,11 @@ func (conn *Dummy) MarkMessagesSeen(ctx context.Context, messageIDs []imap.Messa
 
 		conn.pushUpdate(imap.NewMessageFlagsUpdated(
 			messageID,
-			conn.state.isSeen(messageID),
-			conn.state.isFlagged(messageID),
-			conn.state.isDraft(messageID),
+			imap.MessageCustomFlags{
+				Seen:    conn.state.isSeen(messageID),
+				Flagged: conn.state.isFlagged(messageID),
+				Draft:   conn.state.isDraft(messageID),
+			},
 		))
 	}
 
@@ -260,9 +268,11 @@ func (conn *Dummy) MarkMessagesFlagged(ctx context.Context, messageIDs []imap.Me
 
 		conn.pushUpdate(imap.NewMessageFlagsUpdated(
 			messageID,
-			conn.state.isSeen(messageID),
-			conn.state.isFlagged(messageID),
-			conn.state.isDraft(messageID),
+			imap.MessageCustomFlags{
+				Seen:    conn.state.isSeen(messageID),
+				Flagged: conn.state.isFlagged(messageID),
+				Draft:   conn.state.isDraft(messageID),
+			},
 		))
 	}
 
diff --git a/connector/dummy_simulate.go b/connector/dummy_simulate.go
index 6325758b..6ffda7e6 100644
--- a/connector/dummy_simulate.go
+++ b/connector/dummy_simulate.go
@@ -166,9 +166,11 @@ func (conn *Dummy) MessageAdded(messageID imap.MessageID, mboxID imap.MailboxID)
 	conn.pushUpdate(imap.NewMessageMailboxesUpdated(
 		messageID,
 		conn.state.getMailboxIDs(messageID),
-		conn.state.isSeen(messageID),
-		conn.state.isFlagged(messageID),
-		conn.state.isDraft(messageID),
+		imap.MessageCustomFlags{
+			Seen:    conn.state.isSeen(messageID),
+			Flagged: conn.state.isFlagged(messageID),
+		    Draft:   conn.state.isDraft(messageID),
+		},
 	))
 
 	return nil
@@ -180,9 +182,11 @@ func (conn *Dummy) MessageRemoved(messageID imap.MessageID, mboxID imap.MailboxI
 	conn.pushUpdate(imap.NewMessageMailboxesUpdated(
 		messageID,
 		conn.state.getMailboxIDs(messageID),
-		conn.state.isSeen(messageID),
-		conn.state.isFlagged(messageID),
-		conn.state.isDraft(messageID),
+		imap.MessageCustomFlags{
+			Seen:    conn.state.isSeen(messageID),
+			Flagged: conn.state.isFlagged(messageID),
+		    Draft:   conn.state.isDraft(messageID),
+		},
 	))
 
 	return nil
@@ -193,9 +197,11 @@ func (conn *Dummy) MessageSeen(messageID imap.MessageID, seen bool) error {
 
 	conn.pushUpdate(imap.NewMessageFlagsUpdated(
 		messageID,
-		conn.state.isSeen(messageID),
-		conn.state.isFlagged(messageID),
-		conn.state.isDraft(messageID),
+		imap.MessageCustomFlags{
+			Seen:    conn.state.isSeen(messageID),
+			Flagged: conn.state.isFlagged(messageID),
+		    Draft:   conn.state.isDraft(messageID),
+		},
 	))
 
 	return nil
@@ -206,9 +212,11 @@ func (conn *Dummy) MessageFlagged(messageID imap.MessageID, flagged bool) error
 
 	conn.pushUpdate(imap.NewMessageFlagsUpdated(
 		messageID,
-		conn.state.isSeen(messageID),
-		conn.state.isFlagged(messageID),
-		conn.state.isDraft(messageID),
+		imap.MessageCustomFlags{
+			Seen:    conn.state.isSeen(messageID),
+			Flagged: conn.state.isFlagged(messageID),
+		    Draft:   conn.state.isDraft(messageID),
+		},
 	))
 
 	return nil
diff --git a/imap/update_message_flags_updated.go b/imap/update_message_flags_updated.go
index 1e0886db..27af8b3d 100644
--- a/imap/update_message_flags_updated.go
+++ b/imap/update_message_flags_updated.go
@@ -9,26 +9,22 @@ type MessageFlagsUpdated struct {
 
 	*updateWaiter
 
-	MessageID            MessageID
-	Seen, Flagged, Draft bool
+	MessageID   MessageID
+	CustomFlags MessageCustomFlags
 }
 
-func NewMessageFlagsUpdated(messageID MessageID, seen, flagged, draft bool) *MessageFlagsUpdated {
+func NewMessageFlagsUpdated(messageID MessageID, flags MessageCustomFlags) *MessageFlagsUpdated {
 	return &MessageFlagsUpdated{
 		updateWaiter: newUpdateWaiter(),
 		MessageID:    messageID,
-		Seen:         seen,
-		Flagged:      flagged,
-		Draft:        draft,
+		CustomFlags:  flags,
 	}
 }
 
 func (u *MessageFlagsUpdated) String() string {
 	return fmt.Sprintf(
-		"MessageFlagsUpdated: MessageID = %v, seen = %v, flagged = %v, draft = %v",
+		"MessageFlagsUpdated: MessageID = %v, CustomFlags = %v",
 		u.MessageID.ShortID(),
-		u.Seen,
-		u.Flagged,
-		u.Draft,
+		u.CustomFlags,
 	)
 }
diff --git a/imap/update_message_labels_updated.go b/imap/update_message_labels_updated.go
index ae110af0..7a0e1e7d 100644
--- a/imap/update_message_labels_updated.go
+++ b/imap/update_message_labels_updated.go
@@ -11,29 +11,33 @@ type MessageMailboxesUpdated struct {
 
 	*updateWaiter
 
-	MessageID            MessageID
-	MailboxIDs           []MailboxID
-	Seen, Flagged, Draft bool
+	MessageID   MessageID
+	MailboxIDs  []MailboxID
+	CustomFlags MessageCustomFlags
 }
 
-func NewMessageMailboxesUpdated(messageID MessageID, mailboxIDs []MailboxID, seen, flagged, draft bool) *MessageMailboxesUpdated {
+type MessageCustomFlags struct {
+	Seen, Flagged, Draft, Answered bool
+}
+
+func (f MessageCustomFlags) String() string {
+	return fmt.Sprintf("seen=%v, flagged=%v, draft=%v, answered=%v", f.Seen, f.Flagged, f.Draft, f.Answered)
+}
+
+func NewMessageMailboxesUpdated(messageID MessageID, mailboxIDs []MailboxID, flags MessageCustomFlags) *MessageMailboxesUpdated {
 	return &MessageMailboxesUpdated{
 		updateWaiter: newUpdateWaiter(),
 		MessageID:    messageID,
 		MailboxIDs:   mailboxIDs,
-		Seen:         seen,
-		Flagged:      flagged,
-		Draft:        draft,
+		CustomFlags:  flags,
 	}
 }
 
 func (u *MessageMailboxesUpdated) String() string {
 	return fmt.Sprintf(
-		"MessageMailboxesUpdated: MessageID = %v, MailboxIDs = %v, seen = %v, flagged = %v, draft = %v",
+		"MessageMailboxesUpdated: MessageID = %v, MailboxIDs = %v, CustomFlags = %v",
 		u.MessageID.ShortID(),
 		xslices.Map(u.MailboxIDs, func(id MailboxID) string { return id.ShortID() }),
-		u.Seen,
-		u.Flagged,
-		u.Draft,
+		u.CustomFlags,
 	)
 }
diff --git a/internal/backend/connector_updates.go b/internal/backend/connector_updates.go
index faa80b7b..82097bbd 100644
--- a/internal/backend/connector_updates.go
+++ b/internal/backend/connector_updates.go
@@ -365,7 +365,7 @@ func (user *user) applyMessageMailboxesUpdated(ctx context.Context, update *imap
 			return err
 		}
 
-		if err := user.setMessageFlags(ctx, tx, internalMsgID, update.Seen, update.Flagged, update.Draft); err != nil {
+		if err := user.setMessageFlags(ctx, tx, internalMsgID, update.CustomFlags); err != nil {
 			return err
 		}
 
@@ -393,7 +393,7 @@ func (user *user) applyMessageFlagsUpdated(ctx context.Context, update *imap.Mes
 			return err
 		}
 
-		if err := user.setMessageFlags(ctx, tx, internalMsgID, update.Seen, update.Flagged, update.Draft); err != nil {
+		if err := user.setMessageFlags(ctx, tx, internalMsgID, update.CustomFlags); err != nil {
 			return err
 		}
 
@@ -465,7 +465,7 @@ func (user *user) applyMessagesRemovedFromMailbox(ctx context.Context, tx *ent.T
 	return nil
 }
 
-func (user *user) setMessageFlags(ctx context.Context, tx *ent.Tx, messageID imap.InternalMessageID, seen, flagged, draft bool) error {
+func (user *user) setMessageFlags(ctx context.Context, tx *ent.Tx, messageID imap.InternalMessageID, flags imap.MessageCustomFlags) error {
 	curFlags, err := db.GetMessageFlags(ctx, tx.Client(), []imap.InternalMessageID{messageID})
 	if err != nil {
 		return err
@@ -473,34 +473,34 @@ func (user *user) setMessageFlags(ctx context.Context, tx *ent.Tx, messageID ima
 
 	flagSet := curFlags[0].FlagSet
 
-	if seen && !flagSet.ContainsUnchecked(imap.FlagSeenLowerCase) {
-		if err := user.addMessageFlags(ctx, tx, messageID, imap.FlagSeen); err != nil {
-			return err
-		}
-	} else if !seen && flagSet.ContainsUnchecked(imap.FlagSeenLowerCase) {
-		if err := user.removeMessageFlags(ctx, tx, messageID, imap.FlagSeen); err != nil {
-			return err
+	setFlag := func(flag string, wantFlag bool) error {
+		if wantFlag && !flagSet.Contains(flag) {
+			if err := user.addMessageFlags(ctx, tx, messageID, flag); err != nil {
+				return err
+			}
+		} else if !wantFlag && flagSet.Contains(flag) {
+			if err := user.removeMessageFlags(ctx, tx, messageID, flag); err != nil {
+				return err
+			}
 		}
+
+		return nil
 	}
 
-	if flagged && !flagSet.ContainsUnchecked(imap.FlagFlaggedLowerCase) {
-		if err := user.addMessageFlags(ctx, tx, messageID, imap.FlagFlagged); err != nil {
-			return err
-		}
-	} else if !flagged && flagSet.ContainsUnchecked(imap.FlagFlaggedLowerCase) {
-		if err := user.removeMessageFlags(ctx, tx, messageID, imap.FlagFlagged); err != nil {
-			return err
-		}
+	if err := setFlag(imap.FlagSeen, flags.Seen); err != nil {
+		return err
 	}
 
-	if draft && !flagSet.ContainsUnchecked(imap.FlagDraftLowerCase) {
-		if err := user.addMessageFlags(ctx, tx, messageID, imap.FlagDraft); err != nil {
-			return err
-		}
-	} else if !draft && flagSet.ContainsUnchecked(imap.FlagDraftLowerCase) {
-		if err := user.removeMessageFlags(ctx, tx, messageID, imap.FlagDraft); err != nil {
-			return err
-		}
+	if err := setFlag(imap.FlagFlagged, flags.Flagged); err != nil {
+		return err
+	}
+
+	if err := setFlag(imap.FlagDraft, flags.Draft); err != nil {
+		return err
+	}
+
+	if err := setFlag(imap.FlagAnswered, flags.Answered); err != nil {
+		return err
 	}
 
 	return nil
diff --git a/tests/state_test.go b/tests/state_test.go
index d6e89dc9..4f0f894e 100644
--- a/tests/state_test.go
+++ b/tests/state_test.go
@@ -89,7 +89,7 @@ func TestErrNoSuchMessage(t *testing.T) {
 	}
 
 	runOneToOneTestWithAuth(t, defaultServerOptions(t, withConnectorBuilder(connBuilder)), func(c *testConnection, s *testSession) {
-		update := imap.NewMessageMailboxesUpdated("this is not the message you are looking for", []imap.MailboxID{}, false, false, false)
+		update := imap.NewMessageMailboxesUpdated("this is not the message you are looking for", []imap.MailboxID{}, imap.MessageCustomFlags{})
 
 		connBuilder.updateCh <- update