diff --git a/config/bridge.go b/config/bridge.go
index a27d976b2..9bbd83dfc 100644
--- a/config/bridge.go
+++ b/config/bridge.go
@@ -95,27 +95,28 @@ type BridgeConfig struct {
 
 	DoublePuppetConfig bridgeconfig.DoublePuppetConfig `yaml:",inline"`
 
-	PrivateChatPortalMeta string `yaml:"private_chat_portal_meta"`
-	ParallelMemberSync    bool   `yaml:"parallel_member_sync"`
-	BridgeNotices         bool   `yaml:"bridge_notices"`
-	ResendBridgeInfo      bool   `yaml:"resend_bridge_info"`
-	MuteBridging          bool   `yaml:"mute_bridging"`
-	ArchiveTag            string `yaml:"archive_tag"`
-	PinnedTag             string `yaml:"pinned_tag"`
-	TagOnlyOnCreate       bool   `yaml:"tag_only_on_create"`
-	MarkReadOnlyOnCreate  bool   `yaml:"mark_read_only_on_create"`
-	EnableStatusBroadcast bool   `yaml:"enable_status_broadcast"`
-	MuteStatusBroadcast   bool   `yaml:"mute_status_broadcast"`
-	StatusBroadcastTag    string `yaml:"status_broadcast_tag"`
-	WhatsappThumbnail     bool   `yaml:"whatsapp_thumbnail"`
-	AllowUserInvite       bool   `yaml:"allow_user_invite"`
-	FederateRooms         bool   `yaml:"federate_rooms"`
-	URLPreviews           bool   `yaml:"url_previews"`
-	CaptionInMessage      bool   `yaml:"caption_in_message"`
-	BeeperGalleries       bool   `yaml:"beeper_galleries"`
-	ExtEvPolls            bool   `yaml:"extev_polls"`
-	CrossRoomReplies      bool   `yaml:"cross_room_replies"`
-	DisableReplyFallbacks bool   `yaml:"disable_reply_fallbacks"`
+	PrivateChatPortalMeta  string `yaml:"private_chat_portal_meta"`
+	ParallelMemberSync     bool   `yaml:"parallel_member_sync"`
+	BridgeNotices          bool   `yaml:"bridge_notices"`
+	ResendBridgeInfo       bool   `yaml:"resend_bridge_info"`
+	MuteBridging           bool   `yaml:"mute_bridging"`
+	ArchiveTag             string `yaml:"archive_tag"`
+	PinnedTag              string `yaml:"pinned_tag"`
+	TagOnlyOnCreate        bool   `yaml:"tag_only_on_create"`
+	MarkReadOnlyOnCreate   bool   `yaml:"mark_read_only_on_create"`
+	EnableStatusBroadcast  bool   `yaml:"enable_status_broadcast"`
+	MuteStatusBroadcast    bool   `yaml:"mute_status_broadcast"`
+	StatusBroadcastTag     string `yaml:"status_broadcast_tag"`
+	WhatsappThumbnail      bool   `yaml:"whatsapp_thumbnail"`
+	AllowUserInvite        bool   `yaml:"allow_user_invite"`
+	FederateRooms          bool   `yaml:"federate_rooms"`
+	URLPreviews            bool   `yaml:"url_previews"`
+	CaptionInMessage       bool   `yaml:"caption_in_message"`
+	BeeperGalleries        bool   `yaml:"beeper_galleries"`
+	ExtEvPolls             bool   `yaml:"extev_polls"`
+	CrossRoomReplies       bool   `yaml:"cross_room_replies"`
+	DisableReplyFallbacks  bool   `yaml:"disable_reply_fallbacks"`
+	PrivateChatSelfPuppets bool   `yaml:"private_chat_self_puppets"`
 
 	MessageHandlingTimeout struct {
 		ErrorAfterStr string `yaml:"error_after"`
diff --git a/config/upgrade.go b/config/upgrade.go
index b7917c74f..f5cea4316 100644
--- a/config/upgrade.go
+++ b/config/upgrade.go
@@ -119,6 +119,7 @@ func DoUpgrade(helper *up.Helper) {
 	}
 	helper.Copy(up.Bool, "bridge", "cross_room_replies")
 	helper.Copy(up.Bool, "bridge", "disable_reply_fallbacks")
+	helper.Copy(up.Bool, "bridge", "private_chat_self_puppets")
 	helper.Copy(up.Str|up.Null, "bridge", "message_handling_timeout", "error_after")
 	helper.Copy(up.Str|up.Null, "bridge", "message_handling_timeout", "deadline")
 
diff --git a/example-config.yaml b/example-config.yaml
index 25ddf9403..a9fbd86a9 100644
--- a/example-config.yaml
+++ b/example-config.yaml
@@ -321,6 +321,10 @@ bridge:
     # Disable generating reply fallbacks? Some extremely bad clients still rely on them,
     # but they're being phased out and will be completely removed in the future.
     disable_reply_fallbacks: false
+    # Invite the puppet which represents the bridge user into private chats?
+    # This allows proper backfilling in private chats without double puppeting enabled,
+    # but adds an additional puppet user to each private chat.
+    private_chat_self_puppets: false
     # Maximum time for handling Matrix events. Duration strings formatted for https://pkg.go.dev/time#ParseDuration
     # Null means there's no enforced timeout.
     message_handling_timeout:
diff --git a/portal.go b/portal.go
index da365f357..b28ce1901 100644
--- a/portal.go
+++ b/portal.go
@@ -1217,7 +1217,7 @@ func (portal *Portal) getMessageIntent(ctx context.Context, user *User, info *ty
 		return nil
 	}
 	intent := puppet.IntentFor(portal)
-	if !intent.IsCustomPuppet && portal.IsPrivateChat() && info.Sender.User == portal.Key.Receiver.User && portal.Key.Receiver != portal.Key.JID {
+	if !portal.bridge.Config.Bridge.PrivateChatSelfPuppets && !intent.IsCustomPuppet && portal.IsPrivateChat() && info.Sender.User == portal.Key.Receiver.User && portal.Key.Receiver != portal.Key.JID {
 		zerolog.Ctx(ctx).Debug().Msg("Not handling message: user doesn't have double puppeting enabled")
 		return nil
 	}
@@ -2181,6 +2181,10 @@ func (portal *Portal) CreateMatrixRoom(ctx context.Context, user *User, groupInf
 			invite = append(invite, portal.bridge.Bot.UserID)
 		}
 	}
+	if portal.IsPrivateChat() && portal.bridge.Config.Bridge.PrivateChatSelfPuppets {
+		rec := portal.bridge.GetPuppetByJID(portal.Key.Receiver)
+		invite = append(invite, rec.MXID)
+	}
 	if !portal.AvatarURL.IsEmpty() && portal.shouldSetDMRoomMetadata() {
 		initialState = append(initialState, &event.Event{
 			Type: event.StateRoomAvatar,
@@ -2304,6 +2308,13 @@ func (portal *Portal) CreateMatrixRoom(ctx context.Context, user *User, groupInf
 				log.Err(err).Msg("Failed to ensure bridge bot is joined to created portal")
 			}
 		}
+		if portal.bridge.Config.Bridge.PrivateChatSelfPuppets {
+			rec := portal.bridge.GetPuppetByJID(portal.Key.Receiver)
+			err = rec.DefaultIntent().EnsureJoined(ctx, portal.MXID)
+			if err != nil {
+				log.Err(err).Msg("Failed to join created portal with puppet")
+			}
+		}
 
 		user.UpdateDirectChats(ctx, map[id.UserID][]id.RoomID{puppet.MXID: {portal.MXID}})
 	} else if portal.IsParent {