diff --git a/commands.go b/commands.go
index 577bd22..6ea0839 100644
--- a/commands.go
+++ b/commands.go
@@ -363,7 +363,7 @@ func fnCreate(ce *WrappedCommandEvent) {
 	}
 
 	ce.Log.Infofln("Creating group for %s with name %s and participants %+v", ce.RoomID, roomNameEvent.Name, participants)
-	resp, err := ce.User.Client.CreateGroup(roomNameEvent.Name, participants)
+	resp, err := ce.User.Client.CreateGroup(roomNameEvent.Name, participants, "")
 	if err != nil {
 		ce.Reply("Failed to create group: %v", err)
 		return
diff --git a/config/bridge.go b/config/bridge.go
index acefc97..bd22a87 100644
--- a/config/bridge.go
+++ b/config/bridge.go
@@ -21,6 +21,7 @@ import (
 	"fmt"
 	"strings"
 	"text/template"
+	"time"
 
 	"go.mau.fi/whatsmeow/types"
 
@@ -109,6 +110,9 @@ type BridgeConfig struct {
 	URLPreviews           bool   `yaml:"url_previews"`
 	CaptionInMessage      bool   `yaml:"caption_in_message"`
 
+	MessageHandlingDeadlineStr string        `yaml:"message_handling_deadline"`
+	MessageHandlingDeadline    time.Duration `yaml:"-"`
+
 	DisableStatusBroadcastSend   bool `yaml:"disable_status_broadcast_send"`
 	DisappearingMessagesInGroups bool `yaml:"disappearing_messages_in_groups"`
 
@@ -195,6 +199,13 @@ func (bc *BridgeConfig) UnmarshalYAML(unmarshal func(interface{}) error) error {
 		return err
 	}
 
+	if bc.MessageHandlingDeadlineStr != "" {
+		bc.MessageHandlingDeadline, err = time.ParseDuration(bc.MessageHandlingDeadlineStr)
+		if err != nil {
+			return err
+		}
+	}
+
 	return nil
 }
 
diff --git a/config/upgrade.go b/config/upgrade.go
index 67bf9d4..f251e96 100644
--- a/config/upgrade.go
+++ b/config/upgrade.go
@@ -91,6 +91,8 @@ func DoUpgrade(helper *up.Helper) {
 	helper.Copy(up.Bool, "bridge", "disable_bridge_alerts")
 	helper.Copy(up.Bool, "bridge", "url_previews")
 	helper.Copy(up.Bool, "bridge", "caption_in_message")
+	helper.Copy(up.Str|up.Null, "bridge", "message_handling_deadline")
+
 	helper.Copy(up.Str, "bridge", "management_room_text", "welcome")
 	helper.Copy(up.Str, "bridge", "management_room_text", "welcome_connected")
 	helper.Copy(up.Str, "bridge", "management_room_text", "welcome_unconnected")
diff --git a/example-config.yaml b/example-config.yaml
index b3acb22..90dca26 100644
--- a/example-config.yaml
+++ b/example-config.yaml
@@ -280,6 +280,9 @@ bridge:
     # Send captions in the same message as images. This will send data compatible with both MSC2530 and MSC3552.
     # This is currently not supported in most clients.
     caption_in_message: false
+    # Maximum time for handling Matrix events. A duration string formatted for https://pkg.go.dev/time#ParseDuration
+    # Null means there's no enforced timeout.
+    message_handling_deadline: null
 
     # The prefix for commands. Only required in non-management rooms.
     command_prefix: "!wa"
diff --git a/go.mod b/go.mod
index 9f6b56c..c67b9f6 100644
--- a/go.mod
+++ b/go.mod
@@ -10,12 +10,12 @@ require (
 	github.com/prometheus/client_golang v1.12.2-0.20220613221938-ebd77f036066
 	github.com/skip2/go-qrcode v0.0.0-20200617195104-da1b6568686e
 	github.com/tidwall/gjson v1.14.1
-	go.mau.fi/whatsmeow v0.0.0-20220628131901-3f187acf2229
+	go.mau.fi/whatsmeow v0.0.0-20220629162100-72294010aba7
 	golang.org/x/image v0.0.0-20220617043117-41969df76e82
 	golang.org/x/net v0.0.0-20220624214902-1bab6f366d9e
 	google.golang.org/protobuf v1.28.0
 	maunium.net/go/maulogger/v2 v2.3.2
-	maunium.net/go/mautrix v0.11.1-0.20220628090842-e9aa4b6f3ac8
+	maunium.net/go/mautrix v0.11.1-0.20220629165511-d505965036ef
 )
 
 require (
diff --git a/go.sum b/go.sum
index ff5cb65..a7f7ab2 100644
--- a/go.sum
+++ b/go.sum
@@ -64,8 +64,8 @@ github.com/yuin/goldmark v1.4.12 h1:6hffw6vALvEDqJ19dOJvJKOoAOKe4NDaTqvd2sktGN0=
 github.com/yuin/goldmark v1.4.12/go.mod h1:6yULJ656Px+3vBD8DxQVa3kxgyrAnzto9xy5taEt/CY=
 go.mau.fi/libsignal v0.0.0-20220628090436-4d18b66b087e h1:ByHDg+D+dMIGuBA2n+1xOUf4xr3FJFYg8yxl06s1YBE=
 go.mau.fi/libsignal v0.0.0-20220628090436-4d18b66b087e/go.mod h1:RCdzkTWSJv0AKGqurzPXJsEGIVMuQps3E/h7CMUPous=
-go.mau.fi/whatsmeow v0.0.0-20220628131901-3f187acf2229 h1:iTJ65cHF4PKn9pTUnbPus6FdFeLXSOvm04FwJwq11hA=
-go.mau.fi/whatsmeow v0.0.0-20220628131901-3f187acf2229/go.mod h1:hsjqq2xLuoFew8vbsDCJcGf5EbXCRcR/yoQ+87w6m3k=
+go.mau.fi/whatsmeow v0.0.0-20220629162100-72294010aba7 h1:W3wefHGUb4WheA49V9bNK4hNugAqr49XyYRvUb/WC7Y=
+go.mau.fi/whatsmeow v0.0.0-20220629162100-72294010aba7/go.mod h1:hsjqq2xLuoFew8vbsDCJcGf5EbXCRcR/yoQ+87w6m3k=
 golang.org/x/crypto v0.0.0-20220622213112-05595931fe9d h1:sK3txAijHtOK88l68nt020reeT1ZdKLIYetKl95FzVY=
 golang.org/x/crypto v0.0.0-20220622213112-05595931fe9d/go.mod h1:IxCIyHEi3zRg3s0A5j5BB6A9Jmi73HwBIUl50j+osU4=
 golang.org/x/image v0.0.0-20220617043117-41969df76e82 h1:KpZB5pUSBvrHltNEdK/tw0xlPeD13M6M6aGP32gKqiw=
@@ -108,5 +108,5 @@ maunium.net/go/mauflag v1.0.0 h1:YiaRc0tEI3toYtJMRIfjP+jklH45uDHtT80nUamyD4M=
 maunium.net/go/mauflag v1.0.0/go.mod h1:nLivPOpTpHnpzEh8jEdSL9UqO9+/KBJFmNRlwKfkPeA=
 maunium.net/go/maulogger/v2 v2.3.2 h1:1XmIYmMd3PoQfp9J+PaHhpt80zpfmMqaShzUTC7FwY0=
 maunium.net/go/maulogger/v2 v2.3.2/go.mod h1:TYWy7wKwz/tIXTpsx8G3mZseIRiC5DoMxSZazOHy68A=
-maunium.net/go/mautrix v0.11.1-0.20220628090842-e9aa4b6f3ac8 h1:c5xjJlWALgEVLN3CWA77PrEvyGb9yrAcCq/9RJ/+Ubo=
-maunium.net/go/mautrix v0.11.1-0.20220628090842-e9aa4b6f3ac8/go.mod h1:Lj4pBam5P0zIvieIFHnGsuaj+xfFtI3y/sC8yGlyna8=
+maunium.net/go/mautrix v0.11.1-0.20220629165511-d505965036ef h1:v5axLh3G3cNDNEOn8vCJpafSk4hp7I+aYjmoTq6OjlY=
+maunium.net/go/mautrix v0.11.1-0.20220629165511-d505965036ef/go.mod h1:Lj4pBam5P0zIvieIFHnGsuaj+xfFtI3y/sC8yGlyna8=
diff --git a/portal.go b/portal.go
index 9155a55..a52b025 100644
--- a/portal.go
+++ b/portal.go
@@ -967,6 +967,7 @@ func (user *User) updateAvatar(jid types.JID, avatarID *string, avatarURL *id.Co
 		}
 		*avatarURL = url
 	}
+	log.Debugfln("Updated avatar %s -> %s", *avatarID, avatar.ID)
 	*avatarID = avatar.ID
 	*avatarSet = false
 	return true
@@ -2777,12 +2778,12 @@ func createJPEGThumbnail(source []byte) ([]byte, error) {
 	return data, err
 }
 
-func (portal *Portal) downloadThumbnail(original []byte, thumbnailURL id.ContentURIString, eventID id.EventID) ([]byte, error) {
+func (portal *Portal) downloadThumbnail(ctx context.Context, original []byte, thumbnailURL id.ContentURIString, eventID id.EventID) ([]byte, error) {
 	if len(thumbnailURL) == 0 {
 		// just fall back to making thumbnail of original
 	} else if mxc, err := thumbnailURL.Parse(); err != nil {
 		portal.log.Warnfln("Malformed thumbnail URL in %s: %v (falling back to generating thumbnail from source)", eventID, err)
-	} else if thumbnail, err := portal.MainIntent().DownloadBytes(mxc); err != nil {
+	} else if thumbnail, err := portal.MainIntent().DownloadBytesContext(ctx, mxc); err != nil {
 		portal.log.Warnfln("Failed to download thumbnail in %s: %v (falling back to generating thumbnail from source)", eventID, err)
 	} else {
 		return createJPEGThumbnail(thumbnail)
@@ -2804,7 +2805,7 @@ func (portal *Portal) convertWebPtoPNG(webpImage []byte) ([]byte, error) {
 	return pngBuffer.Bytes(), nil
 }
 
-func (portal *Portal) preprocessMatrixMedia(sender *User, relaybotFormatted bool, content *event.MessageEventContent, eventID id.EventID, mediaType whatsmeow.MediaType) (*MediaUpload, error) {
+func (portal *Portal) preprocessMatrixMedia(ctx context.Context, sender *User, relaybotFormatted bool, content *event.MessageEventContent, eventID id.EventID, mediaType whatsmeow.MediaType) (*MediaUpload, error) {
 	var caption string
 	var mentionedJIDs []string
 	if relaybotFormatted {
@@ -2821,7 +2822,7 @@ func (portal *Portal) preprocessMatrixMedia(sender *User, relaybotFormatted bool
 	if err != nil {
 		return nil, err
 	}
-	data, err := portal.MainIntent().DownloadBytes(mxc)
+	data, err := portal.MainIntent().DownloadBytesContext(ctx, mxc)
 	if err != nil {
 		return nil, util.NewDualError(errMediaDownloadFailed, err)
 	}
@@ -2832,7 +2833,7 @@ func (portal *Portal) preprocessMatrixMedia(sender *User, relaybotFormatted bool
 		}
 	}
 	if mediaType == whatsmeow.MediaVideo && content.GetInfo().MimeType == "image/gif" {
-		data, err = ffmpeg.ConvertBytes(data, ".mp4", []string{"-f", "gif"}, []string{
+		data, err = ffmpeg.ConvertBytes(ctx, data, ".mp4", []string{"-f", "gif"}, []string{
 			"-pix_fmt", "yuv420p", "-c:v", "libx264", "-movflags", "+faststart",
 			"-filter:v", "crop='floor(in_w/2)*2:floor(in_h/2)*2'",
 		}, content.GetInfo().MimeType)
@@ -2848,7 +2849,7 @@ func (portal *Portal) preprocessMatrixMedia(sender *User, relaybotFormatted bool
 		}
 		content.Info.MimeType = "image/png"
 	}
-	uploadResp, err := sender.Client.Upload(context.Background(), data, mediaType)
+	uploadResp, err := sender.Client.Upload(ctx, data, mediaType)
 	if err != nil {
 		return nil, util.NewDualError(errMediaWhatsAppUploadFailed, err)
 	}
@@ -2856,7 +2857,7 @@ func (portal *Portal) preprocessMatrixMedia(sender *User, relaybotFormatted bool
 	// Audio doesn't have thumbnails
 	var thumbnail []byte
 	if mediaType != whatsmeow.MediaAudio {
-		thumbnail, err = portal.downloadThumbnail(data, content.GetInfo().ThumbnailURL, eventID)
+		thumbnail, err = portal.downloadThumbnail(ctx, data, content.GetInfo().ThumbnailURL, eventID)
 		// Ignore format errors for non-image files, we don't care about those thumbnails
 		if err != nil && (!errors.Is(err, image.ErrFormat) || mediaType == whatsmeow.MediaImage) {
 			portal.log.Warnfln("Failed to generate thumbnail for %s: %v", eventID, err)
@@ -2947,7 +2948,7 @@ func getUnstableWaveform(content map[string]interface{}) []byte {
 	return output
 }
 
-func (portal *Portal) convertMatrixMessage(sender *User, evt *event.Event) (*waProto.Message, *User, error) {
+func (portal *Portal) convertMatrixMessage(ctx context.Context, sender *User, evt *event.Event) (*waProto.Message, *User, error) {
 	content, ok := evt.Content.Parsed.(*event.MessageEventContent)
 	if !ok {
 		return nil, sender, fmt.Errorf("%w %T", errUnexpectedParsedContentType, evt.Content.Parsed)
@@ -3003,14 +3004,17 @@ func (portal *Portal) convertMatrixMessage(sender *User, evt *event.Event) (*waP
 			Text:        &text,
 			ContextInfo: &ctxInfo,
 		}
-		hasPreview := portal.convertURLPreviewToWhatsApp(sender, evt, msg.ExtendedTextMessage)
+		hasPreview := portal.convertURLPreviewToWhatsApp(ctx, sender, evt, msg.ExtendedTextMessage)
+		if ctx.Err() != nil {
+			return nil, nil, ctx.Err()
+		}
 		if ctxInfo.StanzaId == nil && ctxInfo.MentionedJid == nil && ctxInfo.Expiration == nil && !hasPreview {
 			// No need for extended message
 			msg.ExtendedTextMessage = nil
 			msg.Conversation = &text
 		}
 	case event.MsgImage:
-		media, err := portal.preprocessMatrixMedia(sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaImage)
+		media, err := portal.preprocessMatrixMedia(ctx, sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaImage)
 		if media == nil {
 			return nil, sender, err
 		}
@@ -3028,7 +3032,7 @@ func (portal *Portal) convertMatrixMessage(sender *User, evt *event.Event) (*waP
 		}
 	case event.MsgVideo:
 		gifPlayback := content.GetInfo().MimeType == "image/gif"
-		media, err := portal.preprocessMatrixMedia(sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaVideo)
+		media, err := portal.preprocessMatrixMedia(ctx, sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaVideo)
 		if media == nil {
 			return nil, sender, err
 		}
@@ -3048,7 +3052,7 @@ func (portal *Portal) convertMatrixMessage(sender *User, evt *event.Event) (*waP
 			FileLength:    proto.Uint64(uint64(media.FileLength)),
 		}
 	case event.MsgAudio:
-		media, err := portal.preprocessMatrixMedia(sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaAudio)
+		media, err := portal.preprocessMatrixMedia(ctx, sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaAudio)
 		if media == nil {
 			return nil, sender, err
 		}
@@ -3071,7 +3075,7 @@ func (portal *Portal) convertMatrixMessage(sender *User, evt *event.Event) (*waP
 			msg.AudioMessage.Mimetype = proto.String(addCodecToMime(content.GetInfo().MimeType, "opus"))
 		}
 	case event.MsgFile:
-		media, err := portal.preprocessMatrixMedia(sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaDocument)
+		media, err := portal.preprocessMatrixMedia(ctx, sender, relaybotFormatted, content, evt.ID, whatsmeow.MediaDocument)
 		if media == nil {
 			return nil, sender, err
 		}
@@ -3159,6 +3163,8 @@ func errorToStatusReason(err error) (reason event.MessageStatusReason, isCertain
 		errors.Is(err, errBroadcastReactionNotSupported),
 		errors.Is(err, errBroadcastSendDisabled):
 		return event.MessageStatusUnsupported, true, false, true
+	case errors.Is(err, context.DeadlineExceeded):
+		return event.MessageStatusTooOld, false, true, true
 	case errors.Is(err, errTargetNotFound),
 		errors.Is(err, errTargetIsFake),
 		errors.Is(err, errReactionDatabaseNotFound),
@@ -3179,10 +3185,13 @@ func errorToStatusReason(err error) (reason event.MessageStatusReason, isCertain
 	}
 }
 
-func (portal *Portal) sendStatusEvent(evtID id.EventID, err error) {
+func (portal *Portal) sendStatusEvent(evtID, lastRetry id.EventID, err error) {
 	if !portal.bridge.Config.Bridge.MessageStatusEvents {
 		return
 	}
+	if lastRetry == evtID {
+		lastRetry = ""
+	}
 	intent := portal.bridge.Bot
 	if !portal.Encrypted {
 		// Bridge bot isn't present in unencrypted DMs
@@ -3194,7 +3203,8 @@ func (portal *Portal) sendStatusEvent(evtID id.EventID, err error) {
 			Type:    event.RelReference,
 			EventID: evtID,
 		},
-		Success: err == nil,
+		Success:   err == nil,
+		LastRetry: lastRetry,
 	}
 	if !content.Success {
 		reason, isCertain, canRetry, _ := errorToStatusReason(err)
@@ -3247,6 +3257,10 @@ func (portal *Portal) sendMessageMetrics(evt *event.Event, err error, part strin
 	if evt.Type == event.EventRedaction {
 		evtDescription += fmt.Sprintf(" of %s", evt.Redacts)
 	}
+	origEvtID := evt.ID
+	if retryMeta := evt.Content.AsMessage().MessageSendRetry; retryMeta != nil {
+		origEvtID = retryMeta.OriginalEventID
+	}
 	if err != nil {
 		level := log.LevelError
 		if part == "Ignoring" {
@@ -3259,12 +3273,12 @@ func (portal *Portal) sendMessageMetrics(evt *event.Event, err error, part strin
 		if sendNotice {
 			portal.sendErrorMessage(err.Error(), isCertain)
 		}
-		portal.sendStatusEvent(evt.ID, err)
+		portal.sendStatusEvent(origEvtID, evt.ID, err)
 	} else {
 		portal.log.Debugfln("Handled Matrix %s %s", msgType, evtDescription)
 		portal.sendDeliveryReceipt(evt.ID)
 		portal.bridge.SendMessageSuccessCheckpoint(evt, bridge.MsgStepRemote, 0)
-		portal.sendStatusEvent(evt.ID, nil)
+		portal.sendStatusEvent(origEvtID, evt.ID, nil)
 	}
 }
 
@@ -3276,17 +3290,45 @@ func (portal *Portal) HandleMatrixMessage(sender *User, evt *event.Event) {
 		go portal.sendMessageMetrics(evt, errBroadcastSendDisabled, "Ignoring")
 		return
 	}
-	portal.log.Debugfln("Received message %s from %s", evt.ID, evt.Sender)
-	msg, sender, err := portal.convertMatrixMessage(sender, evt)
+	origEvtID := evt.ID
+	var dbMsg *database.Message
+	if retryMeta := evt.Content.AsMessage().MessageSendRetry; retryMeta != nil {
+		origEvtID = retryMeta.OriginalEventID
+		dbMsg = portal.bridge.DB.Message.GetByMXID(origEvtID)
+		if dbMsg != nil && dbMsg.Sent {
+			portal.log.Debugfln("Ignoring retry request %s (#%d) for %s/%s from %s as message was already sent", evt.ID, retryMeta.RetryCount, origEvtID, dbMsg.JID, evt.Sender)
+			go portal.sendMessageMetrics(evt, nil, "")
+			return
+		} else if dbMsg != nil {
+			portal.log.Debugfln("Got retry request %s (#%d) for %s/%s from %s", evt.ID, retryMeta.RetryCount, origEvtID, dbMsg.JID, evt.Sender)
+		} else {
+			portal.log.Debugfln("Got retry request %s (#%d) for %s from %s (original message not known)", evt.ID, retryMeta.RetryCount, origEvtID, evt.Sender)
+		}
+	} else {
+		portal.log.Debugfln("Received message %s from %s", evt.ID, evt.Sender)
+	}
+
+	ctx := context.Background()
+	if portal.bridge.Config.Bridge.MessageHandlingDeadline > 0 {
+		var cancel context.CancelFunc
+		ctx, cancel = context.WithTimeout(ctx, portal.bridge.Config.Bridge.MessageHandlingDeadline)
+		defer cancel()
+	}
+
+	msg, sender, err := portal.convertMatrixMessage(ctx, sender, evt)
 	if msg == nil {
 		go portal.sendMessageMetrics(evt, err, "Error converting")
 		return
 	}
-	portal.MarkDisappearing(evt.ID, portal.ExpirationTime, true)
+	portal.MarkDisappearing(origEvtID, portal.ExpirationTime, true)
 	info := portal.generateMessageInfo(sender)
-	dbMsg := portal.markHandled(nil, nil, info, evt.ID, false, true, database.MsgNormal, database.MsgNoError)
+	if dbMsg == nil {
+		dbMsg = portal.markHandled(nil, nil, info, evt.ID, false, true, database.MsgNormal, database.MsgNoError)
+	} else {
+		info.ID = dbMsg.JID
+	}
 	portal.log.Debugln("Sending event", evt.ID, "to WhatsApp", info.ID)
-	ts, err := sender.Client.SendMessage(portal.Key.JID, info.ID, msg)
+	ts, err := sender.Client.SendMessage(ctx, portal.Key.JID, info.ID, msg)
 	go portal.sendMessageMetrics(evt, err, "Error sending")
 	if err == nil {
 		dbMsg.MarkSent(ts)
@@ -3346,7 +3388,7 @@ func (portal *Portal) sendReactionToWhatsApp(sender *User, id types.MessageID, t
 		messageKeyParticipant = proto.String(target.Sender.ToNonAD().String())
 	}
 	key = variationselector.Remove(key)
-	return sender.Client.SendMessage(portal.Key.JID, id, &waProto.Message{
+	return sender.Client.SendMessage(context.TODO(), portal.Key.JID, id, &waProto.Message{
 		ReactionMessage: &waProto.ReactionMessage{
 			Key: &waProto.MessageKey{
 				RemoteJid:   proto.String(portal.Key.JID.String()),
diff --git a/urlpreview.go b/urlpreview.go
index 3a0a17e..ad6f368 100644
--- a/urlpreview.go
+++ b/urlpreview.go
@@ -113,7 +113,7 @@ func (portal *Portal) convertURLPreviewToBeeper(intent *appservice.IntentAPI, so
 
 var URLRegex = regexp.MustCompile(`https?://[^\s/_*]+(?:/\S*)?`)
 
-func (portal *Portal) convertURLPreviewToWhatsApp(sender *User, evt *event.Event, dest *waProto.ExtendedTextMessage) bool {
+func (portal *Portal) convertURLPreviewToWhatsApp(ctx context.Context, sender *User, evt *event.Event, dest *waProto.ExtendedTextMessage) bool {
 	var preview *BeeperLinkPreview
 
 	rawPreview := gjson.GetBytes(evt.Content.VeryRaw, `com\.beeper\.linkpreviews`)
@@ -163,7 +163,7 @@ func (portal *Portal) convertURLPreviewToWhatsApp(sender *User, evt *event.Event
 		imageMXC = preview.ImageEncryption.URL.ParseOrIgnore()
 	}
 	if !imageMXC.IsEmpty() {
-		data, err := portal.MainIntent().DownloadBytes(imageMXC)
+		data, err := portal.MainIntent().DownloadBytesContext(ctx, imageMXC)
 		if err != nil {
 			portal.log.Errorfln("Failed to download URL preview image %s in %s: %v", preview.ImageURL, evt.ID, err)
 			return true
@@ -176,7 +176,7 @@ func (portal *Portal) convertURLPreviewToWhatsApp(sender *User, evt *event.Event
 			}
 		}
 		dest.MediaKeyTimestamp = proto.Int64(time.Now().Unix())
-		uploadResp, err := sender.Client.Upload(context.Background(), data, whatsmeow.MediaLinkThumbnail)
+		uploadResp, err := sender.Client.Upload(ctx, data, whatsmeow.MediaLinkThumbnail)
 		if err != nil {
 			portal.log.Errorfln("Failed to upload URL preview thumbnail in %s: %v", evt.ID, err)
 			return true
diff --git a/user.go b/user.go
index dd1830d..c337457 100644
--- a/user.go
+++ b/user.go
@@ -671,7 +671,7 @@ func (user *User) sendHackyPhonePing() {
 	} else {
 		user.log.Warnfln("Failed to get last app state key ID to send hacky phone ping: %v - sending empty request", err)
 	}
-	ts, err := user.Client.SendMessage(user.JID.ToNonAD(), msgID, &waProto.Message{
+	ts, err := user.Client.SendMessage(context.Background(), user.JID.ToNonAD(), msgID, &waProto.Message{
 		ProtocolMessage: &waProto.ProtocolMessage{
 			Type: waProto.ProtocolMessage_APP_STATE_SYNC_KEY_REQUEST.Enum(),
 			AppStateSyncKeyRequest: &waProto.AppStateSyncKeyRequest{