diff --git a/bridge/matrix.go b/bridge/matrix.go
index 9e305d0..7e4686a 100644
--- a/bridge/matrix.go
+++ b/bridge/matrix.go
@@ -199,11 +199,11 @@ func (mh *matrixHandler) handleMembership(evt *event.Event) {
 		return
 	}
 
+	puppet := mh.bridge.GetPuppetByMXID(id.UserID(evt.GetStateKey()))
+
 	// Load or create a new portal.
 	portal := mh.bridge.GetPortalByMXID(evt.RoomID)
 	if portal == nil {
-		puppet := mh.bridge.GetPuppetByMXID(id.UserID(evt.GetStateKey()))
-
 		if content.Membership == event.MembershipInvite && puppet != nil {
 			mh.handlePuppetInvite(evt, user, puppet)
 		}
@@ -213,7 +213,20 @@ func (mh *matrixHandler) handleMembership(evt *event.Event) {
 
 	isSelf := id.UserID(evt.GetStateKey()) == evt.Sender
 
-	if content.Membership == event.MembershipInvite && !isSelf {
-		portal.HandleMatrixInvite(user, evt)
+	if content.Membership == event.MembershipLeave {
+		if evt.Unsigned.PrevContent != nil {
+			_ = evt.Unsigned.PrevContent.ParseRaw(evt.Type)
+			prevContent, ok := evt.Unsigned.PrevContent.Parsed.(*event.MemberEventContent)
+			if ok && prevContent.Membership != "join" {
+				return
+			}
+		}
+		if isSelf {
+			portal.handleMatrixLeave(user)
+		} else if puppet != nil {
+			portal.handleMatrixKick(user, puppet)
+		}
+	} else if content.Membership == event.MembershipInvite && !isSelf {
+		portal.handleMatrixInvite(user, evt)
 	}
 }
diff --git a/bridge/portal.go b/bridge/portal.go
index 9f7bd88..620fc8e 100644
--- a/bridge/portal.go
+++ b/bridge/portal.go
@@ -136,7 +136,7 @@ func (b *Bridge) NewPortal(dbPortal *database.Portal) *Portal {
 	return portal
 }
 
-func (p *Portal) HandleMatrixInvite(sender *User, evt *event.Event) {
+func (p *Portal) handleMatrixInvite(sender *User, evt *event.Event) {
 	// Look up an existing puppet or create a new one.
 	puppet := p.bridge.GetPuppetByMXID(id.UserID(evt.GetStateKey()))
 	if puppet != nil {
@@ -354,3 +354,113 @@ func (p *Portal) handleMatrixMessage(sender *User, evt *event.Event) {
 	sender.Session.ChannelMessageSend(p.Key.ChannelID, content.Body)
 	p.log.Debugln("sent message:", content.Body)
 }
+
+func (p *Portal) handleMatrixLeave(sender *User) {
+	if p.IsPrivateChat() {
+		p.log.Debugln("User left private chat portal, cleaning up and deleting...")
+		p.delete()
+		p.cleanup(false)
+
+		return
+	}
+
+	// TODO: figure out how to close a dm from the API.
+
+	p.cleanupIfEmpty()
+}
+
+func (p *Portal) delete() {
+	p.Portal.Delete()
+	p.bridge.portalsLock.Lock()
+	delete(p.bridge.portalsByID, p.Key)
+
+	if p.MXID != "" {
+		delete(p.bridge.portalsByMXID, p.MXID)
+	}
+
+	p.bridge.portalsLock.Unlock()
+}
+
+func (p *Portal) cleanupIfEmpty() {
+	users, err := p.getMatrixUsers()
+	if err != nil {
+		p.log.Errorfln("Failed to get Matrix user list to determine if portal needs to be cleaned up: %v", err)
+
+		return
+	}
+
+	if len(users) == 0 {
+		p.log.Infoln("Room seems to be empty, cleaning up...")
+		p.delete()
+		p.cleanup(false)
+	}
+}
+
+func (p *Portal) cleanup(puppetsOnly bool) {
+	if p.MXID != "" {
+		return
+	}
+
+	if p.IsPrivateChat() {
+		_, err := p.MainIntent().LeaveRoom(p.MXID)
+		if err != nil {
+			p.log.Warnln("Failed to leave private chat portal with main intent:", err)
+		}
+
+		return
+	}
+
+	intent := p.MainIntent()
+	members, err := intent.JoinedMembers(p.MXID)
+	if err != nil {
+		p.log.Errorln("Failed to get portal members for cleanup:", err)
+
+		return
+	}
+
+	for member := range members.Joined {
+		if member == intent.UserID {
+			continue
+		}
+
+		puppet := p.bridge.GetPuppetByMXID(member)
+		if p != nil {
+			_, err = puppet.DefaultIntent().LeaveRoom(p.MXID)
+			if err != nil {
+				p.log.Errorln("Error leaving as puppet while cleaning up portal:", err)
+			}
+		} else if !puppetsOnly {
+			_, err = intent.KickUser(p.MXID, &mautrix.ReqKickUser{UserID: member, Reason: "Deleting portal"})
+			if err != nil {
+				p.log.Errorln("Error kicking user while cleaning up portal:", err)
+			}
+		}
+	}
+
+	_, err = intent.LeaveRoom(p.MXID)
+	if err != nil {
+		p.log.Errorln("Error leaving with main intent while cleaning up portal:", err)
+	}
+}
+
+func (p *Portal) getMatrixUsers() ([]id.UserID, error) {
+	members, err := p.MainIntent().JoinedMembers(p.MXID)
+	if err != nil {
+		return nil, fmt.Errorf("failed to get member list: %w", err)
+	}
+
+	var users []id.UserID
+	for userID := range members.Joined {
+		_, isPuppet := p.bridge.ParsePuppetMXID(userID)
+		if !isPuppet && userID != p.bridge.bot.UserID {
+			users = append(users, userID)
+		}
+	}
+
+	return users, nil
+}
+
+func (p *Portal) handleMatrixKick(sender *User, target *Puppet) {
+	// TODO: need to learn how to make this happen as discordgo proper doesn't
+	// support group dms and it looks like it's a binary blob.
+}
diff --git a/database/portal.go b/database/portal.go
index e47c0ec..ceb6a00 100644
--- a/database/portal.go
+++ b/database/portal.go
@@ -68,3 +68,11 @@ func (p *Portal) Update() {
 		p.log.Warnfln("Failed to update %s: %v", p.Key, err)
 	}
 }
+
+func (p *Portal) Delete() {
+	query := "DELETE FROM portal WHERE channel_id=$1 AND receiver=$2"
+	_, err := p.db.Exec(query, p.Key.ChannelID, p.Key.Receiver)
+	if err != nil {
+		p.log.Warnfln("Failed to delete %s: %v", p.Key, err)
+	}
+}