diff --git a/pkg/connector/backfill.go b/pkg/connector/backfill.go
index 8f006e0b..e2c7d114 100644
--- a/pkg/connector/backfill.go
+++ b/pkg/connector/backfill.go
@@ -293,7 +293,10 @@ func (wa *WhatsAppClient) handleWAHistorySync(
 		for i, rawMsg := range rawMessages {
 			// Don't store messages that will just be skipped.
 			msgEvt, err := wa.Client.ParseWebMessage(jid, rawMsg.GetMessage())
-			if err != nil {
+			if err != nil && getMessageType(rawMsg.GetMessage().GetMessage()) == "ignore" {
+				ignoredTypes++
+				continue
+			} else if err != nil {
 				log.Warn().Err(err).
 					Int("msg_index", i).
 					Str("msg_id", rawMsg.GetMessage().GetKey().GetID()).
diff --git a/pkg/connector/handlematrix.go b/pkg/connector/handlematrix.go
index 935d7628..84198506 100644
--- a/pkg/connector/handlematrix.go
+++ b/pkg/connector/handlematrix.go
@@ -273,12 +273,9 @@ func (wa *WhatsAppClient) HandleMatrixEdit(ctx context.Context, edit *bridgev2.M
 		return fmt.Errorf("failed to parse portal ID: %w", err)
 	}
 
-	waMsg := wa.Main.MsgConv.CaptionEditToWhatsApp(ctx, wa.Client, edit.Event, edit.Content, edit.Portal)
-	if waMsg == nil {
-		waMsg, _, err = wa.Main.MsgConv.ToWhatsApp(ctx, wa.Client, edit.Event, edit.Content, nil, nil, edit.Portal)
-		if err != nil {
-			return wrapConversionError(fmt.Errorf("failed to convert message: %w", err))
-		}
+	waMsg, _, err := wa.Main.MsgConv.ToWhatsApp(ctx, wa.Client, edit.Event, edit.Content, nil, nil, edit.Portal)
+	if err != nil {
+		return wrapConversionError(fmt.Errorf("failed to convert message: %w", err))
 	}
 	defer wa.mcTrack(edit, time.Now(), &retErr)
 
diff --git a/pkg/msgconv/from-matrix.go b/pkg/msgconv/from-matrix.go
index c45a2205..ba2adc23 100644
--- a/pkg/msgconv/from-matrix.go
+++ b/pkg/msgconv/from-matrix.go
@@ -204,46 +204,6 @@ func (mc *MessageConverter) ToWhatsApp(
 	return message, extra, nil
 }
 
-func (mc *MessageConverter) CaptionEditToWhatsApp(
-	ctx context.Context,
-	client *whatsmeow.Client,
-	evt *event.Event,
-	content *event.MessageEventContent,
-	portal *bridgev2.Portal,
-) *waE2E.Message {
-	mime := content.GetInfo().MimeType
-	if mime == "" {
-		return nil
-	} else if mime == "image/gif" {
-		content.MsgType = event.MsgVideo
-	}
-	ctx = context.WithValue(ctx, contextKeyClient, client)
-	ctx = context.WithValue(ctx, contextKeyPortal, portal)
-	contextInfo := mc.generateContextInfo(ctx, nil, content.RelatesTo, portal, content.BeeperDisappearingTimer, content.Mentions != nil && content.Mentions.Room)
-	msg := mc.constructMediaMessage(ctx, content, evt, &whatsmeow.UploadResponse{}, nil, contextInfo, mime)
-	switch {
-	case msg.GetImageMessage() != nil:
-		return &waE2E.Message{ImageMessage: &waE2E.ImageMessage{
-			Caption:     msg.ImageMessage.Caption,
-			ContextInfo: contextInfo,
-		}}
-	case msg.GetVideoMessage() != nil:
-		return &waE2E.Message{VideoMessage: &waE2E.VideoMessage{
-			Caption:     msg.VideoMessage.Caption,
-			ContextInfo: contextInfo,
-		}}
-	case msg.GetDocumentMessage() != nil, msg.GetDocumentWithCaptionMessage() != nil:
-		return &waE2E.Message{DocumentWithCaptionMessage: &waE2E.FutureProofMessage{
-			Message: &waE2E.Message{DocumentMessage: &waE2E.DocumentMessage{
-				Caption:     proto.String(msg.GetDocumentWithCaptionMessage().GetMessage().GetDocumentMessage().GetCaption()),
-				ContextInfo: contextInfo,
-			}},
-		}}
-	default:
-		return nil
-	}
-}
-
 func (mc *MessageConverter) constructMediaMessage(
 	ctx context.Context,
 	content *event.MessageEventContent,
diff --git a/pkg/msgconv/from-whatsapp.go b/pkg/msgconv/from-whatsapp.go
index db18f35a..ec273076 100644
--- a/pkg/msgconv/from-whatsapp.go
+++ b/pkg/msgconv/from-whatsapp.go
@@ -322,6 +322,7 @@ func (mc *MessageConverter) ToMatrix(
 		cm.ThreadRoot = ptr.Ptr(waid.MakeMessageID(chat, pcp, commentTarget.GetID()))
 	}
 	mc.cutOffLongMessage(part.Content)
+	logOversizedPart(ctx, part)
 
 	return cm
 }
diff --git a/pkg/msgconv/wa-text.go b/pkg/msgconv/wa-text.go
index 52874fd8..7afcc81f 100644
--- a/pkg/msgconv/wa-text.go
+++ b/pkg/msgconv/wa-text.go
@@ -18,6 +18,7 @@ package msgconv
 
 import (
 	"context"
+	"encoding/json"
 	"fmt"
 	"html"
 	"regexp"
@@ -25,6 +26,7 @@ import (
 	"strconv"
 	"strings"
 
+	"github.com/rs/zerolog"
 	"go.mau.fi/whatsmeow/proto/waE2E"
 	"maunium.net/go/mautrix/bridgev2"
 	"maunium.net/go/mautrix/event"
@@ -72,6 +74,36 @@ func (mc *MessageConverter) cutOffLongMessage(content *event.MessageEventContent
 	}
 }
 
+func logOversizedPart(ctx context.Context, part *bridgev2.ConvertedMessagePart) {
+	if part == nil || part.Content == nil {
+		return
+	}
+	contentJSON, _ := json.Marshal(part.Content)
+	extraJSON, _ := json.Marshal(part.Extra)
+	if len(contentJSON)+len(extraJSON) <= 40000 {
+		return
+	}
+	extraKeys := make([]string, 0, len(part.Extra))
+	for key := range part.Extra {
+		extraKeys = append(extraKeys, key)
+	}
+	var mentionCount int
+	if part.Content.Mentions != nil {
+		mentionCount = len(part.Content.Mentions.UserIDs)
+	}
+	linkPreviewJSON, _ := json.Marshal(part.Content.BeeperLinkPreviews)
+	zerolog.Ctx(ctx).Warn().
+		Str("msg_type", string(part.Content.MsgType)).
+		Int("content_json_size", len(contentJSON)).
+		Int("extra_json_size", len(extraJSON)).
+		Int("body_size", len(part.Content.Body)).
+		Int("formatted_body_size", len(part.Content.FormattedBody)).
+		Int("mention_count", mentionCount).
+		Int("link_preview_json_size", len(linkPreviewJSON)).
+		Strs("extra_keys", extraKeys).
+		Msg("Converted message part is larger than the cut-off limit")
+}
+
 func (mc *MessageConverter) parseFormatting(content *event.MessageEventContent, allowInlineURL, forceHTML bool) {
 	parsedHTML := parseWAFormattingToHTML(content.Body, allowInlineURL)
 	if forceHTML || parsedHTML != event.TextToHTML(content.Body) {