diff --git a/pkg/hicli/html.go b/pkg/hicli/html.go
index af92864..bcc9fbb 100644
--- a/pkg/hicli/html.go
+++ b/pkg/hicli/html.go
@@ -330,7 +330,7 @@ func matrixURIClassName(uri *id.MatrixURI) string {
 	}
 }
 
-func writeA(w *strings.Builder, attr []html.Attribute) {
+func writeA(w *strings.Builder, attr []html.Attribute) (mxc id.ContentURI) {
 	w.WriteString("<a")
 	href := parseAAttributes(attr)
 	if href == "" {
@@ -365,8 +365,9 @@ func writeA(w *strings.Builder, attr []html.Attribute) {
 		newTab = false
 		writeAttribute(w, "class", matrixURIClassName(uri))
 	case "mxc":
-		mxc := id.ContentURIString(href).ParseOrIgnore()
+		mxc = id.ContentURIString(href).ParseOrIgnore()
 		if !mxc.IsValid() {
+			mxc = id.ContentURI{}
 			return
 		}
 		href = fmt.Sprintf(HTMLSanitizerImgSrcTemplate, mxc.Homeserver, mxc.FileID)
@@ -378,11 +379,12 @@ func writeA(w *strings.Builder, attr []html.Attribute) {
 		writeAttribute(w, "target", "_blank")
 		writeAttribute(w, "rel", "noreferrer noopener")
 	}
+	return
 }
 
 var HTMLSanitizerImgSrcTemplate = "mxc://%s/%s"
 
-func writeImg(w *strings.Builder, attr []html.Attribute) {
+func writeImg(w *strings.Builder, attr []html.Attribute) id.ContentURI {
 	src, alt, title, isCustomEmoji, width, height := parseImgAttributes(attr)
 	w.WriteString("<img")
 	writeAttribute(w, "alt", alt)
@@ -391,7 +393,7 @@ func writeImg(w *strings.Builder, attr []html.Attribute) {
 	}
 	mxc := id.ContentURIString(src).ParseOrIgnore()
 	if !mxc.IsValid() {
-		return
+		return id.ContentURI{}
 	}
 	writeAttribute(w, "src", fmt.Sprintf(HTMLSanitizerImgSrcTemplate, mxc.Homeserver, mxc.FileID))
 	writeAttribute(w, "loading", "lazy")
@@ -403,6 +405,7 @@ func writeImg(w *strings.Builder, attr []html.Attribute) {
 	} else {
 		writeAttribute(w, "class", "hicli-sizeless-inline-img")
 	}
+	return mxc
 }
 
 func writeSpan(w *strings.Builder, attr []html.Attribute) {
@@ -454,9 +457,10 @@ func (ts *tagStack) pop(tag atom.Atom) bool {
 	return false
 }
 
-func sanitizeAndLinkifyHTML(body string) (string, error) {
+func sanitizeAndLinkifyHTML(body string) (string, []id.ContentURI, error) {
 	tz := html.NewTokenizer(strings.NewReader(body))
 	var built strings.Builder
+	var inlineImages []id.ContentURI
 	ts := make(tagStack, 2)
 Loop:
 	for {
@@ -466,7 +470,7 @@ Loop:
 			if errors.Is(err, io.EOF) {
 				break Loop
 			}
-			return "", err
+			return "", nil, err
 		case html.StartTagToken, html.SelfClosingTagToken:
 			token := tz.Token()
 			if !tagIsAllowed(token.DataAtom) {
@@ -478,9 +482,15 @@ Loop:
 			}
 			switch token.DataAtom {
 			case atom.A:
-				writeA(&built, token.Attr)
+				mxc := writeA(&built, token.Attr)
+				if !mxc.IsEmpty() {
+					inlineImages = append(inlineImages, mxc)
+				}
 			case atom.Img:
-				writeImg(&built, token.Attr)
+				mxc := writeImg(&built, token.Attr)
+				if !mxc.IsEmpty() {
+					inlineImages = append(inlineImages, mxc)
+				}
 			case atom.Span, atom.Font:
 				writeSpan(&built, token.Attr)
 			default:
@@ -524,5 +534,5 @@ Loop:
 		built.WriteString(t.String())
 		built.WriteByte('>')
 	}
-	return built.String(), nil
+	return built.String(), inlineImages, nil
 }
diff --git a/pkg/hicli/send.go b/pkg/hicli/send.go
index 42a8a1e..058601e 100644
--- a/pkg/hicli/send.go
+++ b/pkg/hicli/send.go
@@ -137,11 +137,17 @@ func (h *HiClient) Send(
 		}
 		dbEvt.RelatesTo, dbEvt.RelationType = database.GetRelatesToFromBytes(dbEvt.Content)
 	}
-	dbEvt.LocalContent = h.calculateLocalContent(ctx, dbEvt, dbEvt.AsRawMautrix())
+	var inlineImages []id.ContentURI
+	mautrixEvt := dbEvt.AsRawMautrix()
+	dbEvt.LocalContent, inlineImages = h.calculateLocalContent(ctx, dbEvt, mautrixEvt)
 	_, err = h.DB.Event.Insert(ctx, dbEvt)
 	if err != nil {
 		return nil, fmt.Errorf("failed to insert event into database: %w", err)
 	}
+	h.cacheMedia(ctx, mautrixEvt, dbEvt.RowID)
+	for _, uri := range inlineImages {
+		h.addMediaCache(ctx, dbEvt.RowID, uri.CUString(), nil, nil, "")
+	}
 	ctx = context.WithoutCancel(ctx)
 	go func() {
 		err := h.SetTyping(ctx, room.ID, 0)
diff --git a/pkg/hicli/sync.go b/pkg/hicli/sync.go
index d0fbda2..36c59b3 100644
--- a/pkg/hicli/sync.go
+++ b/pkg/hicli/sync.go
@@ -343,14 +343,14 @@ func (h *HiClient) cacheMedia(ctx context.Context, evt *event.Event, rowID datab
 	}
 }
 
-func (h *HiClient) calculateLocalContent(ctx context.Context, dbEvt *database.Event, evt *event.Event) *database.LocalContent {
+func (h *HiClient) calculateLocalContent(ctx context.Context, dbEvt *database.Event, evt *event.Event) (*database.LocalContent, []id.ContentURI) {
 	if evt.Type != event.EventMessage {
-		return nil
+		return nil, nil
 	}
 	_ = evt.Content.ParseRaw(evt.Type)
 	content, ok := evt.Content.Parsed.(*event.MessageEventContent)
 	if !ok {
-		return nil
+		return nil, nil
 	}
 	if dbEvt.RelationType == event.RelReplace && content.NewContent != nil {
 		content = content.NewContent
@@ -358,8 +358,21 @@ func (h *HiClient) calculateLocalContent(ctx context.Context, dbEvt *database.Ev
 	if content != nil {
 		var sanitizedHTML string
 		var wasPlaintext bool
+		var inlineImages []id.ContentURI
 		if content.Format == event.FormatHTML && content.FormattedBody != "" {
-			sanitizedHTML, _ = sanitizeAndLinkifyHTML(content.FormattedBody)
+			var err error
+			sanitizedHTML, inlineImages, err = sanitizeAndLinkifyHTML(content.FormattedBody)
+			if err != nil {
+				zerolog.Ctx(ctx).Warn().Err(err).
+					Stringer("event_id", dbEvt.ID).
+					Msg("Failed to sanitize HTML")
+			}
+			if len(inlineImages) > 0 && dbEvt.RowID != 0 {
+				for _, uri := range inlineImages {
+					h.addMediaCache(ctx, dbEvt.RowID, uri.CUString(), nil, nil, "")
+				}
+				inlineImages = nil
+			}
 		} else {
 			var builder strings.Builder
 			linkifyAndWriteBytes(&builder, []byte(content.Body))
@@ -370,9 +383,9 @@ func (h *HiClient) calculateLocalContent(ctx context.Context, dbEvt *database.Ev
 			SanitizedHTML: sanitizedHTML,
 			HTMLVersion:   CurrentHTMLSanitizerVersion,
 			WasPlaintext:  wasPlaintext,
-		}
+		}, inlineImages
 	}
-	return nil
+	return nil, nil
 }
 
 const CurrentHTMLSanitizerVersion = 2
@@ -381,7 +394,7 @@ func (h *HiClient) ReprocessExistingEvent(ctx context.Context, evt *database.Eve
 	if evt.Type != event.EventMessage.Type || evt.LocalContent == nil || evt.LocalContent.HTMLVersion >= CurrentHTMLSanitizerVersion {
 		return
 	}
-	evt.LocalContent = h.calculateLocalContent(ctx, evt, evt.AsRawMautrix())
+	evt.LocalContent, _ = h.calculateLocalContent(ctx, evt, evt.AsRawMautrix())
 	err := h.DB.Event.UpdateLocalContent(ctx, evt)
 	if err != nil {
 		zerolog.Ctx(ctx).Err(err).
@@ -390,14 +403,15 @@ func (h *HiClient) ReprocessExistingEvent(ctx context.Context, evt *database.Eve
 	}
 }
 
-func (h *HiClient) postDecryptProcess(ctx context.Context, llSummary *mautrix.LazyLoadSummary, dbEvt *database.Event, evt *event.Event) {
+func (h *HiClient) postDecryptProcess(ctx context.Context, llSummary *mautrix.LazyLoadSummary, dbEvt *database.Event, evt *event.Event) (inlineImages []id.ContentURI) {
 	if dbEvt.RowID != 0 {
 		h.cacheMedia(ctx, evt, dbEvt.RowID)
 	}
 	if evt.Sender != h.Account.UserID {
 		dbEvt.UnreadType = h.evaluatePushRules(ctx, llSummary, dbEvt.GetNonPushUnreadType(), evt)
 	}
-	dbEvt.LocalContent = h.calculateLocalContent(ctx, dbEvt, evt)
+	dbEvt.LocalContent, inlineImages = h.calculateLocalContent(ctx, dbEvt, evt)
+	return
 }
 
 func (h *HiClient) processEvent(
@@ -438,10 +452,11 @@ func (h *HiClient) processEvent(
 			evt.Redacts = id.EventID(gjson.GetBytes(evt.Content.VeryRaw, "redacts").Str)
 		}
 	}
+	var inlineImages []id.ContentURI
 	if decryptedMautrixEvt != nil {
-		h.postDecryptProcess(ctx, llSummary, dbEvt, decryptedMautrixEvt)
+		inlineImages = h.postDecryptProcess(ctx, llSummary, dbEvt, decryptedMautrixEvt)
 	} else {
-		h.postDecryptProcess(ctx, llSummary, dbEvt, evt)
+		inlineImages = h.postDecryptProcess(ctx, llSummary, dbEvt, evt)
 	}
 	_, err := h.DB.Event.Upsert(ctx, dbEvt)
 	if err != nil {
@@ -452,6 +467,9 @@ func (h *HiClient) processEvent(
 	} else {
 		h.cacheMedia(ctx, evt, dbEvt.RowID)
 	}
+	for _, uri := range inlineImages {
+		h.addMediaCache(ctx, dbEvt.RowID, uri.CUString(), nil, nil, "")
+	}
 	if decryptionErr != nil && isDecryptionErrorRetryable(decryptionErr) {
 		req, ok := decryptionQueue[dbEvt.MegolmSessionID]
 		if !ok {