diff --git a/database/attachment.go b/database/attachment.go
deleted file mode 100644
index 2a2d1e2..0000000
--- a/database/attachment.go
+++ /dev/null
@@ -1,126 +0,0 @@
-package database
-
-import (
-	"database/sql"
-	"errors"
-
-	log "maunium.net/go/maulogger/v2"
-
-	"maunium.net/go/mautrix/id"
-	"maunium.net/go/mautrix/util/dbutil"
-)
-
-type AttachmentQuery struct {
-	db  *Database
-	log log.Logger
-}
-
-const (
-	attachmentSelect = "SELECT dcid, dc_msg_id, dc_chan_id, dc_chan_receiver, dc_thread_id, mxid FROM attachment"
-)
-
-func (aq *AttachmentQuery) New() *Attachment {
-	return &Attachment{
-		db:  aq.db,
-		log: aq.log,
-	}
-}
-
-func (aq *AttachmentQuery) GetAllByDiscordMessageID(key PortalKey, discordMessageID string) []*Attachment {
-	query := attachmentSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dc_msg_id=$3"
-
-	return aq.getAll(query, key.ChannelID, key.Receiver, discordMessageID)
-}
-
-func (aq *AttachmentQuery) getAll(query string, args ...interface{}) []*Attachment {
-	rows, err := aq.db.Query(query, args...)
-	if err != nil {
-		aq.log.Debugfln("getAll failed: %v", err)
-
-		return nil
-	}
-
-	if rows == nil {
-		return nil
-	}
-
-	var attachments []*Attachment
-	for rows.Next() {
-		attachments = append(attachments, aq.New().Scan(rows))
-	}
-
-	return attachments
-}
-
-func (aq *AttachmentQuery) GetByDiscordID(key PortalKey, discordMessageID, discordID string) *Attachment {
-	query := attachmentSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dc_msg_id=$3 AND dcid=$4"
-
-	return aq.get(query, key.ChannelID, key.Receiver, discordMessageID, discordID)
-}
-
-func (aq *AttachmentQuery) GetByMatrixID(key PortalKey, matrixEventID id.EventID) *Attachment {
-	query := attachmentSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND mxid=$3"
-
-	return aq.get(query, key.ChannelID, key.Receiver, matrixEventID)
-}
-
-func (aq *AttachmentQuery) get(query string, args ...interface{}) *Attachment {
-	row := aq.db.QueryRow(query, args...)
-	if row == nil {
-		return nil
-	}
-
-	return aq.New().Scan(row)
-}
-
-type Attachment struct {
-	db  *Database
-	log log.Logger
-
-	Channel   PortalKey
-	ThreadID  string
-	MessageID string
-	ID        string
-	MXID      id.EventID
-}
-
-func (a *Attachment) DiscordProtoChannelID() string {
-	if a.ThreadID != "" {
-		return a.ThreadID
-	} else {
-		return a.Channel.ChannelID
-	}
-}
-
-func (a *Attachment) Scan(row dbutil.Scannable) *Attachment {
-	err := row.Scan(&a.ID, &a.MessageID, &a.Channel.ChannelID, &a.Channel.Receiver, &a.ThreadID, &a.MXID)
-	if err != nil {
-		if !errors.Is(err, sql.ErrNoRows) {
-			a.log.Errorln("Database scan failed:", err)
-			panic(err)
-		}
-		return nil
-	}
-	return a
-}
-
-func (a *Attachment) Insert() {
-	query := `
-		INSERT INTO attachment (dcid, dc_msg_id, dc_chan_id, dc_chan_receiver, dc_thread_id, mxid)
-		VALUES ($1, $2, $3, $4, $5, $6)
-	`
-	_, err := a.db.Exec(query, a.ID, a.MessageID, a.Channel.ChannelID, a.Channel.Receiver, strPtr(a.ThreadID), a.MXID)
-	if err != nil {
-		a.log.Warnfln("Failed to insert attachment for %s@%s: %v", a.ID, a.Channel, err)
-		panic(err)
-	}
-}
-
-func (a *Attachment) Delete() {
-	query := `DELETE FROM attachment WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dcid=$3`
-	_, err := a.db.Exec(query, a.Channel.ChannelID, a.Channel.Receiver, a.ID)
-	if err != nil {
-		a.log.Warnfln("Failed to delete attachment for %s@%s: %v", a.ID, a.Channel, err)
-		panic(err)
-	}
-}
diff --git a/database/database.go b/database/database.go
index 5a74633..cfd874d 100644
--- a/database/database.go
+++ b/database/database.go
@@ -14,15 +14,14 @@ import (
 type Database struct {
 	*dbutil.Database
 
-	User       *UserQuery
-	Portal     *PortalQuery
-	Puppet     *PuppetQuery
-	Message    *MessageQuery
-	Thread     *ThreadQuery
-	Reaction   *ReactionQuery
-	Attachment *AttachmentQuery
-	Emoji      *EmojiQuery
-	Guild      *GuildQuery
+	User     *UserQuery
+	Portal   *PortalQuery
+	Puppet   *PuppetQuery
+	Message  *MessageQuery
+	Thread   *ThreadQuery
+	Reaction *ReactionQuery
+	Emoji    *EmojiQuery
+	Guild    *GuildQuery
 }
 
 func New(baseDB *dbutil.Database) *Database {
@@ -52,10 +51,6 @@ func New(baseDB *dbutil.Database) *Database {
 		db:  db,
 		log: db.Log.Sub("Reaction"),
 	}
-	db.Attachment = &AttachmentQuery{
-		db:  db,
-		log: db.Log.Sub("Attachment"),
-	}
 	db.Emoji = &EmojiQuery{
 		db:  db,
 		log: db.Log.Sub("Emoji"),
diff --git a/database/message.go b/database/message.go
index 04fe525..1dd692e 100644
--- a/database/message.go
+++ b/database/message.go
@@ -3,6 +3,8 @@ package database
 import (
 	"database/sql"
 	"errors"
+	"fmt"
+	"strings"
 	"time"
 
 	log "maunium.net/go/maulogger/v2"
@@ -17,7 +19,7 @@ type MessageQuery struct {
 }
 
 const (
-	messageSelect = "SELECT dcid, dc_chan_id, dc_chan_receiver, dc_sender, timestamp, dc_thread_id, mxid FROM message"
+	messageSelect = "SELECT dcid, dc_attachment_id, dc_edit_index, dc_chan_id, dc_chan_receiver, dc_sender, timestamp, dc_thread_id, mxid FROM message"
 )
 
 func (mq *MessageQuery) New() *Message {
@@ -27,11 +29,12 @@ func (mq *MessageQuery) New() *Message {
 	}
 }
 
-func (mq *MessageQuery) GetAll(key PortalKey) []*Message {
-	query := messageSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2"
-
-	rows, err := mq.db.Query(query, key.ChannelID, key.Receiver)
-	if err != nil || rows == nil {
+func (mq *MessageQuery) scanAll(rows *sql.Rows, err error) []*Message {
+	if err != nil {
+		mq.log.Warnfln("Failed to query many messages: %v", err)
+		panic(err)
+		return nil
+	} else if rows == nil {
 		return nil
 	}
 
@@ -43,13 +46,18 @@ func (mq *MessageQuery) GetAll(key PortalKey) []*Message {
 	return messages
 }
 
-func (mq *MessageQuery) GetByDiscordID(key PortalKey, discordID string) *Message {
-	query := messageSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dcid=$3"
+func (mq *MessageQuery) GetByDiscordID(key PortalKey, discordID string) []*Message {
+	query := messageSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dcid=$3 AND dc_edit_index=0 ORDER BY dc_attachment_id ASC"
+	return mq.scanAll(mq.db.Query(query, key.ChannelID, key.Receiver, discordID))
+}
+
+func (mq *MessageQuery) GetFirstByDiscordID(key PortalKey, discordID string) *Message {
+	query := messageSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dcid=$3 AND dc_edit_index=0 ORDER BY dc_attachment_id ASC LIMIT 1"
 	return mq.New().Scan(mq.db.QueryRow(query, key.ChannelID, key.Receiver, discordID))
 }
 
 func (mq *MessageQuery) GetLastInThread(key PortalKey, threadID string) *Message {
-	query := messageSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dc_thread_id=$3 ORDER BY timestamp DESC LIMIT 1"
+	query := messageSelect + " WHERE dc_chan_id=$1 AND dc_chan_receiver=$2 AND dc_thread_id=$3 AND dc_edit_index=0 ORDER BY timestamp DESC, dc_attachment_id DESC LIMIT 1"
 	return mq.New().Scan(mq.db.QueryRow(query, key.ChannelID, key.Receiver, threadID))
 }
 
@@ -68,11 +76,13 @@ type Message struct {
 	db  *Database
 	log log.Logger
 
-	DiscordID string
-	Channel   PortalKey
-	SenderID  string
-	Timestamp time.Time
-	ThreadID  string
+	DiscordID    string
+	AttachmentID string
+	EditIndex    int
+	Channel      PortalKey
+	SenderID     string
+	Timestamp    time.Time
+	ThreadID     string
 
 	MXID id.EventID
 }
@@ -89,7 +99,7 @@ func (m *Message) Scan(row dbutil.Scannable) *Message {
 	var ts int64
 	var threadID sql.NullString
 
-	err := row.Scan(&m.DiscordID, &m.Channel.ChannelID, &m.Channel.Receiver, &m.SenderID, &ts, &threadID, &m.MXID)
+	err := row.Scan(&m.DiscordID, &m.AttachmentID, &m.EditIndex, &m.Channel.ChannelID, &m.Channel.Receiver, &m.SenderID, &ts, &threadID, &m.MXID)
 	if err != nil {
 		if !errors.Is(err, sql.ErrNoRows) {
 			m.log.Errorln("Database scan failed:", err)
@@ -107,14 +117,49 @@ func (m *Message) Scan(row dbutil.Scannable) *Message {
 	return m
 }
 
-func (m *Message) Insert() {
-	query := `
-		INSERT INTO message (dcid, dc_chan_id, dc_chan_receiver, dc_sender, timestamp, dc_thread_id, mxid)
-		VALUES ($1, $2, $3, $4, $5, $6, $7)
-	`
+const messageInsertQuery = `
+	INSERT INTO message (
+		dcid, dc_attachment_id, dc_edit_index, dc_chan_id, dc_chan_receiver, dc_sender, timestamp, dc_thread_id, mxid
+	)
+	VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9)
+`
 
-	_, err := m.db.Exec(query,
-		m.DiscordID, m.Channel.ChannelID, m.Channel.Receiver, m.SenderID,
+var messageMassInsertTemplate = strings.Replace(messageInsertQuery, "($1, $2, $3, $4, $5, $6, $7, $8, $9)", "%s", 1)
+
+type MessagePart struct {
+	AttachmentID string
+	MXID         id.EventID
+}
+
+func (m *Message) MassInsert(msgs []MessagePart) {
+	valueStringFormat := "($1, $%d, $2, $3, $4, $5, $6, $7, $%d)"
+	if m.db.Dialect == dbutil.SQLite {
+		valueStringFormat = strings.ReplaceAll(valueStringFormat, "$", "?")
+	}
+	params := make([]interface{}, 7+len(msgs)*2)
+	placeholders := make([]string, len(msgs))
+	params[0] = m.DiscordID
+	params[1] = m.EditIndex
+	params[2] = m.Channel.ChannelID
+	params[3] = m.Channel.Receiver
+	params[4] = m.SenderID
+	params[5] = m.Timestamp.UnixMilli()
+	params[6] = m.ThreadID
+	for i, msg := range msgs {
+		params[7+i*2] = msg.AttachmentID
+		params[7+i*2+1] = msg.MXID
+		placeholders[i] = fmt.Sprintf(valueStringFormat, 7+i*2+1, 7+i*2+2)
+	}
+	_, err := m.db.Exec(fmt.Sprintf(messageMassInsertTemplate, strings.Join(placeholders, ", ")), params...)
+	if err != nil {
+		m.log.Warnfln("Failed to insert %d parts of %s@%s: %v", len(msgs), m.DiscordID, m.Channel, err)
+		panic(err)
+	}
+}
+
+func (m *Message) Insert() {
+	_, err := m.db.Exec(messageInsertQuery,
+		m.DiscordID, m.AttachmentID, m.EditIndex, m.Channel.ChannelID, m.Channel.Receiver, m.SenderID,
 		m.Timestamp.UnixMilli(), strPtr(m.ThreadID), m.MXID)
 
 	if err != nil {
diff --git a/database/reaction.go b/database/reaction.go
index 71584db..99dbca9 100644
--- a/database/reaction.go
+++ b/database/reaction.go
@@ -78,6 +78,8 @@ type Reaction struct {
 	ThreadID  string
 
 	MXID id.EventID
+
+	FirstAttachmentID string
 }
 
 func (r *Reaction) Scan(row dbutil.Scannable) *Reaction {
@@ -105,10 +107,10 @@ func (r *Reaction) DiscordProtoChannelID() string {
 
 func (r *Reaction) Insert() {
 	query := `
-		INSERT INTO reaction (dc_msg_id, dc_sender, dc_emoji_name, dc_chan_id, dc_chan_receiver, dc_thread_id, mxid)
-		VALUES($1, $2, $3, $4, $5, $6, $7)
+		INSERT INTO reaction (dc_msg_id, dc_first_attachment_id, dc_sender, dc_emoji_name, dc_chan_id, dc_chan_receiver, dc_thread_id, mxid)
+		VALUES($1, $2, $3, $4, $5, $6, $7, $8)
 	`
-	_, err := r.db.Exec(query, r.MessageID, r.Sender, r.EmojiName, r.Channel.ChannelID, r.Channel.Receiver, strPtr(r.ThreadID), r.MXID)
+	_, err := r.db.Exec(query, r.MessageID, r.FirstAttachmentID, r.Sender, r.EmojiName, r.Channel.ChannelID, r.Channel.Receiver, strPtr(r.ThreadID), r.MXID)
 	if err != nil {
 		r.log.Warnfln("Failed to insert reaction for %s@%s: %v", r.MessageID, r.Channel, err)
 		panic(err)
diff --git a/database/upgrades/00-latest-revision.sql b/database/upgrades/00-latest-revision.sql
index f272adc..3dc764a 100644
--- a/database/upgrades/00-latest-revision.sql
+++ b/database/upgrades/00-latest-revision.sql
@@ -1,4 +1,4 @@
--- v0 -> v3: Latest revision
+-- v0 -> v4: Latest revision
 
 CREATE TABLE guild (
     dcid       TEXT PRIMARY KEY,
@@ -90,6 +90,8 @@ CREATE TABLE user_portal (
 
 CREATE TABLE message (
     dcid             TEXT,
+    dc_attachment_id TEXT,
+    dc_edit_index    INTEGER,
     dc_chan_id       TEXT,
     dc_chan_receiver TEXT,
     dc_sender        TEXT NOT NULL,
@@ -98,7 +100,7 @@ CREATE TABLE message (
 
     mxid TEXT NOT NULL UNIQUE,
 
-    PRIMARY KEY (dcid, dc_chan_id, dc_chan_receiver),
+    PRIMARY KEY (dcid, dc_attachment_id, dc_edit_index, dc_chan_id, dc_chan_receiver),
     CONSTRAINT message_portal_fkey FOREIGN KEY (dc_chan_id, dc_chan_receiver) REFERENCES portal (dcid, receiver) ON DELETE CASCADE
 );
 
@@ -110,10 +112,13 @@ CREATE TABLE reaction (
     dc_emoji_name    TEXT,
     dc_thread_id     TEXT,
 
+    dc_first_attachment_id TEXT NOT NULL,
+    _dc_first_edit_index   INTEGER NOT NULL DEFAULT 0,
+
     mxid TEXT NOT NULL UNIQUE,
 
     PRIMARY KEY (dc_chan_id, dc_chan_receiver, dc_msg_id, dc_sender, dc_emoji_name),
-    CONSTRAINT reaction_message_fkey FOREIGN KEY (dc_msg_id, dc_chan_id, dc_chan_receiver) REFERENCES message (dcid, dc_chan_id, dc_chan_receiver) ON DELETE CASCADE
+    CONSTRAINT reaction_message_fkey FOREIGN KEY (dc_msg_id, dc_first_attachment_id, _dc_first_edit_index, dc_chan_id, dc_chan_receiver) REFERENCES message (dcid, dc_attachment_id, dc_edit_index, dc_chan_id, dc_chan_receiver) ON DELETE CASCADE
 );
 
 CREATE TABLE attachment (
diff --git a/database/upgrades/04-attachment-fix.sql b/database/upgrades/04-attachment-fix.sql
new file mode 100644
index 0000000..c476afd
--- /dev/null
+++ b/database/upgrades/04-attachment-fix.sql
@@ -0,0 +1,20 @@
+-- v4: Fix storing attachments
+ALTER TABLE reaction DROP CONSTRAINT reaction_message_fkey;
+ALTER TABLE attachment DROP CONSTRAINT attachment_message_fkey;
+ALTER TABLE message DROP CONSTRAINT message_pkey;
+ALTER TABLE message ADD COLUMN dc_attachment_id TEXT NOT NULL DEFAULT '';
+ALTER TABLE message ADD COLUMN dc_edit_index INTEGER NOT NULL DEFAULT 0;
+ALTER TABLE message ALTER COLUMN dc_attachment_id DROP DEFAULT;
+ALTER TABLE message ALTER COLUMN dc_edit_index DROP DEFAULT;
+ALTER TABLE message ADD PRIMARY KEY (dcid, dc_attachment_id, dc_edit_index, dc_chan_id, dc_chan_receiver);
+INSERT INTO message (dcid, dc_attachment_id, dc_edit_index, dc_chan_id, dc_chan_receiver, dc_sender, timestamp, dc_thread_id, mxid)
+    SELECT message.dcid, attachment.dcid, 0, attachment.dc_chan_id, attachment.dc_chan_receiver, message.dc_sender, message.timestamp, attachment.dc_thread_id, attachment.mxid
+    FROM attachment LEFT JOIN message ON attachment.dc_msg_id = message.dcid;
+DROP TABLE attachment;
+
+ALTER TABLE reaction ADD COLUMN dc_first_attachment_id TEXT NOT NULL DEFAULT '';
+ALTER TABLE reaction ALTER COLUMN dc_first_attachment_id DROP DEFAULT;
+ALTER TABLE reaction ADD COLUMN _dc_first_edit_index INTEGER DEFAULT 0;
+ALTER TABLE reaction ADD CONSTRAINT reaction_message_fkey
+    FOREIGN KEY (dc_msg_id, dc_first_attachment_id, _dc_first_edit_index, dc_chan_id, dc_chan_receiver)
+        REFERENCES message(dcid, dc_attachment_id, dc_edit_index, dc_chan_id, dc_chan_receiver);
diff --git a/portal.go b/portal.go
index 2b0706c..c970039 100644
--- a/portal.go
+++ b/portal.go
@@ -459,16 +459,15 @@ func (portal *Portal) ensureUserInvited(user *User) bool {
 	return user.ensureInvited(portal.MainIntent(), portal.MXID, portal.IsPrivateChat())
 }
 
-func (portal *Portal) markMessageHandled(discordID string, mxid id.EventID, authorID string, timestamp time.Time, threadID string) *database.Message {
+func (portal *Portal) markMessageHandled(discordID string, editIndex int, authorID string, timestamp time.Time, threadID string, parts []database.MessagePart) {
 	msg := portal.bridge.DB.Message.New()
 	msg.Channel = portal.Key
 	msg.DiscordID = discordID
-	msg.MXID = mxid
+	msg.EditIndex = editIndex
 	msg.SenderID = authorID
 	msg.Timestamp = timestamp
 	msg.ThreadID = threadID
-	msg.Insert()
-	return msg
+	msg.MassInsert(parts)
 }
 
 func (portal *Portal) sendMediaFailedMessage(intent *appservice.IntentAPI, bridgeErr error) {
@@ -483,7 +482,7 @@ func (portal *Portal) sendMediaFailedMessage(intent *appservice.IntentAPI, bridg
 	}
 }
 
-func (portal *Portal) handleDiscordAttachment(intent *appservice.IntentAPI, msgID string, attachment *discordgo.MessageAttachment, ts time.Time, threadRelation *event.RelatesTo, threadID string) {
+func (portal *Portal) handleDiscordAttachment(intent *appservice.IntentAPI, msgID string, attachment *discordgo.MessageAttachment, ts time.Time, threadRelation *event.RelatesTo, threadID string) *database.MessagePart {
 	// var captionContent *event.MessageEventContent
 
 	// if attachment.Description != "" {
@@ -521,34 +520,27 @@ func (portal *Portal) handleDiscordAttachment(intent *appservice.IntentAPI, msgI
 	data, err := portal.downloadDiscordAttachment(attachment.URL)
 	if err != nil {
 		portal.sendMediaFailedMessage(intent, err)
-
-		return
+		return nil
 	}
 
 	err = portal.uploadMatrixAttachment(intent, data, content)
 	if err != nil {
 		portal.sendMediaFailedMessage(intent, err)
-
-		return
+		return nil
 	}
 
 	resp, err := portal.sendMatrixMessage(intent, event.EventMessage, content, nil, ts.UnixMilli())
 	if err != nil {
 		portal.log.Warnfln("failed to send media message to matrix: %v", err)
 	}
-
-	dbAttachment := portal.bridge.DB.Attachment.New()
-	dbAttachment.Channel = portal.Key
-	dbAttachment.MessageID = msgID
-	dbAttachment.ID = attachment.ID
-	dbAttachment.MXID = resp.EventID
-	dbAttachment.ThreadID = threadID
-	dbAttachment.Insert()
 	// Update the fallback reply event for the next attachment
 	if threadRelation != nil {
 		threadRelation.InReplyTo.EventID = resp.EventID
 	}
-	go portal.sendDeliveryReceipt(resp.EventID)
+	return &database.MessagePart{
+		AttachmentID: attachment.ID,
+		MXID:         resp.EventID,
+	}
 }
 
 func (portal *Portal) handleDiscordMessageCreate(user *User, msg *discordgo.Message, thread *Thread) {
@@ -604,6 +596,7 @@ func (portal *Portal) handleDiscordMessageCreate(user *User, msg *discordgo.Mess
 		threadRelation = (&event.RelatesTo{}).SetThread(thread.RootMXID, lastEventID)
 	}
 
+	var parts []database.MessagePart
 	ts, _ := discordgo.SnowflakeTimestamp(msg.ID)
 	if msg.Content != "" {
 		content := renderDiscordMarkdown(msg.Content)
@@ -612,11 +605,11 @@ func (portal *Portal) handleDiscordMessageCreate(user *User, msg *discordgo.Mess
 		if msg.MessageReference != nil {
 			//key := database.PortalKey{msg.MessageReference.ChannelID, user.ID}
 			replyTo := portal.bridge.DB.Message.GetByDiscordID(portal.Key, msg.MessageReference.MessageID)
-			if replyTo != nil {
+			if len(replyTo) > 0 {
 				if content.RelatesTo == nil {
 					content.RelatesTo = &event.RelatesTo{}
 				}
-				content.RelatesTo.SetReplyTo(replyTo.MXID)
+				content.RelatesTo.SetReplyTo(replyTo[0].MXID)
 			}
 		}
 
@@ -626,7 +619,7 @@ func (portal *Portal) handleDiscordMessageCreate(user *User, msg *discordgo.Mess
 			return
 		}
 
-		portal.markMessageHandled(msg.ID, resp.EventID, msg.Author.ID, ts, threadID)
+		parts = append(parts, database.MessagePart{MXID: resp.EventID})
 		// Update the fallback reply event for attachments
 		if threadRelation != nil {
 			threadRelation.InReplyTo.EventID = resp.EventID
@@ -635,8 +628,12 @@ func (portal *Portal) handleDiscordMessageCreate(user *User, msg *discordgo.Mess
 	}
 
 	for _, attachment := range msg.Attachments {
-		portal.handleDiscordAttachment(intent, msg.ID, attachment, ts, threadRelation, threadID)
+		part := portal.handleDiscordAttachment(intent, msg.ID, attachment, ts, threadRelation, threadID)
+		if part != nil {
+			parts = append(parts, *part)
+		}
 	}
+	portal.markMessageHandled(msg.ID, 0, msg.Author.ID, ts, threadID, parts)
 }
 
 func (portal *Portal) handleDiscordMessageUpdate(user *User, msg *discordgo.Message) {
@@ -653,7 +650,7 @@ func (portal *Portal) handleDiscordMessageUpdate(user *User, msg *discordgo.Mess
 	}
 
 	if msg.Flags == discordgo.MessageFlagsHasThread {
-		portal.bridge.GetThreadByID(msg.ID, existing)
+		portal.bridge.GetThreadByID(msg.ID, existing[0])
 		portal.log.Debugfln("Marked %s as a thread root", msg.ID)
 		// TODO make autojoining configurable
 		//err := user.Session.ThreadJoinWithLocation(msg.ID, discordgo.ThreadJoinLocationContextMenu)
@@ -682,46 +679,12 @@ func (portal *Portal) handleDiscordMessageUpdate(user *User, msg *discordgo.Mess
 
 	intent := portal.bridge.GetPuppetByID(msg.Author.ID).IntentFor(portal)
 
-	if existing == nil {
-		// Due to the differences in Discord and Matrix attachment handling,
-		// existing will return nil if the original message was empty as we
-		// don't store/save those messages so we can determine when we're
-		// working against an attachment and do the attachment lookup instead.
-
-		// Find all the existing attachments and drop them in a map so we can
-		// figure out which, if any have been deleted and clean them up on the
-		// matrix side.
-		attachmentMap := map[string]*database.Attachment{}
-		attachments := portal.bridge.DB.Attachment.GetAllByDiscordMessageID(portal.Key, msg.ID)
-
-		for _, attachment := range attachments {
-			attachmentMap[attachment.ID] = attachment
-		}
-
-		// Now run through the list of attachments on this message and remove
-		// them from the map.
-		for _, attachment := range msg.Attachments {
-			if _, found := attachmentMap[attachment.ID]; found {
-				delete(attachmentMap, attachment.ID)
-			}
-		}
-
-		// Finally run through any attachments still in the map and delete them
-		// on the matrix side and our database.
-		for _, attachment := range attachmentMap {
-			_, err := intent.RedactEvent(portal.MXID, attachment.MXID)
-			if err != nil {
-				portal.log.Warnfln("Failed to remove attachment %s: %v", attachment.MXID, err)
-			}
-
-			attachment.Delete()
-		}
-
+	if msg.Content == "" || existing[0].AttachmentID != "" {
+		portal.log.Debugfln("Dropping non-text edit to %s", msg.ID)
 		return
 	}
-
 	content := renderDiscordMarkdown(msg.Content)
-	content.SetEdit(existing.MXID)
+	content.SetEdit(existing[0].MXID)
 
 	var editTS int64
 	if msg.EditedTimestamp != nil {
@@ -742,33 +705,20 @@ func (portal *Portal) handleDiscordMessageUpdate(user *User, msg *discordgo.Mess
 }
 
 func (portal *Portal) handleDiscordMessageDelete(user *User, msg *discordgo.Message) {
-	// The discord delete message object is pretty empty and doesn't include
-	// the author so we have to use the DMUser from the portal that was added
-	// at creation time if we're a DM. We'll might have similar issues when we
-	// add guild message support, but we'll cross that bridge when we get
-	// there.
-
-	// Find the message that we're working with. This could correctly return
-	// nil if the message was just one or more attachments.
 	existing := portal.bridge.DB.Message.GetByDiscordID(portal.Key, msg.ID)
 	intent := portal.MainIntent()
-
-	if existing != nil {
-		attachments := portal.bridge.DB.Attachment.GetAllByDiscordMessageID(portal.Key, msg.ID)
-		for _, attachment := range attachments {
-			_, err := intent.RedactEvent(portal.MXID, attachment.MXID)
-			if err != nil {
-				portal.log.Warnfln("Failed to redact attachment %s: %v", attachment.MXID, err)
-			}
-			attachment.Delete()
-		}
-
-		resp, err := intent.RedactEvent(portal.MXID, existing.MXID)
+	var lastResp id.EventID
+	for _, dbMsg := range existing {
+		resp, err := intent.RedactEvent(portal.MXID, dbMsg.MXID)
 		if err != nil {
-			portal.log.Warnfln("Failed to redact message %s: %v", existing.MXID, err)
+			portal.log.Warnfln("Failed to redact message %s: %v", dbMsg.MXID, err)
+		} else if resp != nil && resp.EventID != "" {
+			lastResp = resp.EventID
 		}
-		existing.Delete()
-		portal.sendDeliveryReceipt(resp.EventID)
+		dbMsg.Delete()
+	}
+	if lastResp != "" {
+		portal.sendDeliveryReceipt(lastResp)
 	}
 }
 
@@ -1017,6 +967,9 @@ func (portal *Portal) handleMatrixMessage(sender *User, evt *event.Event) {
 		dbMsg := portal.bridge.DB.Message.New()
 		dbMsg.Channel = portal.Key
 		dbMsg.DiscordID = msg.ID
+		if len(msg.Attachments) > 0 {
+			dbMsg.AttachmentID = msg.Attachments[0].ID
+		}
 		dbMsg.MXID = evt.ID
 		dbMsg.SenderID = sender.DiscordID
 		dbMsg.Timestamp, _ = discordgo.SnowflakeTimestamp(msg.ID)
@@ -1161,34 +1114,15 @@ func (portal *Portal) handleMatrixReaction(sender *User, evt *event.Event) {
 		return
 	}
 
-	var discordID, threadID string
-	channelID := portal.Key.ChannelID
-
 	msg := portal.bridge.DB.Message.GetByMXID(portal.Key, reaction.RelatesTo.EventID)
-
-	// Due to the differences in attachments between Discord and Matrix, if a
-	// user reacts to a media message on discord our lookup above will fail
-	// because the relation of matrix media messages to attachments in handled
-	// in the attachments table instead of messages so we need to check that
-	// before continuing.
-	//
-	// This also leads to interesting problems when a Discord message comes in
-	// with multiple attachments. A user can react to each one individually on
-	// Matrix, which will cause us to send it twice. Discord tends to ignore
-	// this, but if the user removes one of them, discord removes it and now
-	// they're out of sync. Perhaps we should add a counter to the reactions
-	// table to keep them in sync and to avoid sending duplicates to Discord.
 	if msg == nil {
-		attachment := portal.bridge.DB.Attachment.GetByMatrixID(portal.Key, reaction.RelatesTo.EventID)
-		if attachment == nil {
-			portal.bridge.SendMessageErrorCheckpoint(evt, bridge.MsgStepRemote, errors.New("unknown reaction target"), true, 0)
-			return
-		}
-		discordID = attachment.MessageID
-		threadID = attachment.ThreadID
-	} else {
-		discordID = msg.DiscordID
-		threadID = msg.ThreadID
+		portal.bridge.SendMessageErrorCheckpoint(evt, bridge.MsgStepRemote, errors.New("unknown reaction target"), true, 0)
+	}
+
+	firstMsg := msg
+	if msg.AttachmentID != "" {
+		firstMsg = portal.bridge.DB.Message.GetFirstByDiscordID(portal.Key, msg.DiscordID)
+		// TODO should the emoji be rerouted to the first message if it's different?
 	}
 
 	// Figure out if this is a custom emoji or not.
@@ -1207,22 +1141,28 @@ func (portal *Portal) handleMatrixReaction(sender *User, evt *event.Event) {
 		emojiID = variationselector.Remove(emojiID)
 	}
 
-	if threadID != "" {
-		channelID = threadID
+	existing := portal.bridge.DB.Reaction.GetByDiscordID(portal.Key, msg.DiscordID, sender.DiscordID, emojiID)
+	if existing != nil {
+		portal.log.Debugfln("Dropping duplicate Matrix reaction %s (already sent as %s)", evt.ID, existing.MXID)
+		portal.bridge.SendMessageSuccessCheckpoint(evt, bridge.MsgStepRemote, 0)
+		portal.sendDeliveryReceipt(evt.ID)
+		return
 	}
-	err := sender.Session.MessageReactionAdd(channelID, discordID, emojiID)
+
+	err := sender.Session.MessageReactionAdd(msg.DiscordProtoChannelID(), msg.DiscordID, emojiID)
 	if err != nil {
-		portal.log.Debugf("Failed to send reaction to %s: %v", discordID, err)
+		portal.log.Debugf("Failed to send reaction to %s: %v", msg.DiscordID, err)
 		portal.bridge.SendMessageErrorCheckpoint(evt, bridge.MsgStepRemote, err, true, 0)
 		return
 	}
 
 	dbReaction := portal.bridge.DB.Reaction.New()
 	dbReaction.Channel = portal.Key
-	dbReaction.MessageID = discordID
+	dbReaction.MessageID = msg.DiscordID
+	dbReaction.FirstAttachmentID = firstMsg.AttachmentID
 	dbReaction.Sender = sender.DiscordID
 	dbReaction.EmojiName = emojiID
-	dbReaction.ThreadID = threadID
+	dbReaction.ThreadID = msg.ThreadID
 	dbReaction.MXID = evt.ID
 	dbReaction.Insert()
 	portal.log.Debugfln("Handled Matrix reaction %s", evt.ID)
@@ -1272,12 +1212,11 @@ func (portal *Portal) handleDiscordReaction(user *User, reaction *discordgo.Mess
 	message := portal.bridge.DB.Message.GetByDiscordID(portal.Key, reaction.MessageID)
 	if message == nil {
 		portal.log.Debugfln("failed to add reaction to message %s: message not found", reaction.MessageID)
-
 		return
 	}
 
 	// Lookup an existing reaction
-	existing := portal.bridge.DB.Reaction.GetByDiscordID(portal.Key, message.DiscordID, reaction.UserID, discordID)
+	existing := portal.bridge.DB.Reaction.GetByDiscordID(portal.Key, message[0].DiscordID, reaction.UserID, discordID)
 	if !add {
 		if existing == nil {
 			portal.log.Debugln("Failed to remove reaction for unknown message", reaction.MessageID)
@@ -1293,13 +1232,13 @@ func (portal *Portal) handleDiscordReaction(user *User, reaction *discordgo.Mess
 		go portal.sendDeliveryReceipt(resp.EventID)
 		return
 	} else if existing != nil {
-		portal.log.Debugfln("Ignoring duplicate reaction %s from %s to %s", discordID, reaction.UserID, message.DiscordID)
+		portal.log.Debugfln("Ignoring duplicate reaction %s from %s to %s", discordID, reaction.UserID, message[0].DiscordID)
 		return
 	}
 
 	content := event.Content{Parsed: &event.ReactionEventContent{
 		RelatesTo: event.RelatesTo{
-			EventID: message.MXID,
+			EventID: message[0].MXID,
 			Type:    event.RelAnnotation,
 			Key:     matrixReaction,
 		},
@@ -1320,7 +1259,8 @@ func (portal *Portal) handleDiscordReaction(user *User, reaction *discordgo.Mess
 	if existing == nil {
 		dbReaction := portal.bridge.DB.Reaction.New()
 		dbReaction.Channel = portal.Key
-		dbReaction.MessageID = message.DiscordID
+		dbReaction.MessageID = message[0].DiscordID
+		dbReaction.FirstAttachmentID = message[0].AttachmentID
 		dbReaction.Sender = reaction.UserID
 		dbReaction.EmojiName = discordID
 		dbReaction.MXID = resp.EventID