diff --git a/database/message.go b/database/message.go
index 847f946..7464e35 100644
--- a/database/message.go
+++ b/database/message.go
@@ -21,6 +21,7 @@ import (
 	"database/sql"
 	"encoding/json"
 	"strings"
+	"time"
 
 	"github.com/Rhymen/go-whatsapp"
 	waProto "github.com/Rhymen/go-whatsapp/binary/proto"
@@ -65,9 +66,13 @@ func (mq *MessageQuery) GetByMXID(mxid id.EventID) *Message {
 }
 
 func (mq *MessageQuery) GetLastInChat(chat PortalKey) *Message {
+	return mq.GetLastInChatBefore(chat, time.Now().Unix()+60)
+}
+
+func (mq *MessageQuery) GetLastInChatBefore(chat PortalKey, maxTimestamp int64) *Message {
 	msg := mq.get("SELECT chat_jid, chat_receiver, jid, mxid, sender, timestamp, sent, content "+
-		"FROM message WHERE chat_jid=$1 AND chat_receiver=$2 AND sent=true ORDER BY timestamp DESC LIMIT 1",
-		chat.JID, chat.Receiver)
+		"FROM message WHERE chat_jid=$1 AND chat_receiver=$2 AND timestamp<=$3 AND sent=true ORDER BY timestamp DESC LIMIT 1",
+		chat.JID, chat.Receiver, maxTimestamp)
 	if msg == nil || msg.Timestamp == 0 {
 		// Old db, we don't know what the last message is.
 		return nil
diff --git a/go.mod b/go.mod
index 9dc2316..fd75404 100644
--- a/go.mod
+++ b/go.mod
@@ -15,4 +15,4 @@ require (
 	maunium.net/go/mautrix v0.9.12
 )
 
-replace github.com/Rhymen/go-whatsapp => github.com/tulir/go-whatsapp v0.5.2
+replace github.com/Rhymen/go-whatsapp => github.com/tulir/go-whatsapp v0.5.3
diff --git a/go.sum b/go.sum
index dda3ea6..d4e4f56 100644
--- a/go.sum
+++ b/go.sum
@@ -468,6 +468,8 @@ github.com/tulir/go-whatsapp v0.5.1 h1:nJ+ggQrO4kpNdE7VfM6y7J4xezoIHivrAlUjDpQSO
 github.com/tulir/go-whatsapp v0.5.1/go.mod h1:7J3IIL3bEQiBJGtiZst1N4PgXHlWIartdVQLe6lcx9A=
 github.com/tulir/go-whatsapp v0.5.2 h1:CJcFSAoD/vXybamd9Hfa67Otg11G4EfoIgciQakunps=
 github.com/tulir/go-whatsapp v0.5.2/go.mod h1:7J3IIL3bEQiBJGtiZst1N4PgXHlWIartdVQLe6lcx9A=
+github.com/tulir/go-whatsapp v0.5.3 h1:e3bPLCmbBF146l8tnswqxnVLtGCWOEruJSR4luySh6I=
+github.com/tulir/go-whatsapp v0.5.3/go.mod h1:7J3IIL3bEQiBJGtiZst1N4PgXHlWIartdVQLe6lcx9A=
 github.com/urfave/cli v1.20.0/go.mod h1:70zkFmudgCuE/ngEzBv17Jvp/497gISqfk5gWijbERA=
 github.com/urfave/cli v1.22.1 h1:+mkCCcOFKPnCmVYVcURKps1Xe+3zP90gSYGNfRkjoIY=
 github.com/urfave/cli v1.22.1/go.mod h1:Gos4lmkARVdJ6EkW0WaNv/tZAAMe9V7XWyB60NtXRu0=
diff --git a/user.go b/user.go
index 453c81d..6188d02 100644
--- a/user.go
+++ b/user.go
@@ -756,7 +756,7 @@ func (user *User) syncChatDoublePuppetDetails(doublePuppet *Puppet, chat Chat, j
 	}
 	intent := doublePuppet.CustomIntent()
 	if chat.UnreadCount == 0 && (justCreated || !user.bridge.Config.Bridge.MarkReadOnlyOnCreate) {
-		lastMessage := user.bridge.DB.Message.GetLastInChat(chat.Portal.Key)
+		lastMessage := user.bridge.DB.Message.GetLastInChatBefore(chat.Portal.Key, chat.ReceivedAt.Unix())
 		if lastMessage != nil {
 			err := intent.MarkReadWithContent(chat.Portal.MXID, lastMessage.MXID, &CustomReadReceipt{DoublePuppet: true})
 			if err != nil {