diff --git a/database/upgrades/2018-09-01-initial-schema.go b/database/upgrades/2018-09-01-initial-schema.go
index 189d3d0..3e0c7c6 100644
--- a/database/upgrades/2018-09-01-initial-schema.go
+++ b/database/upgrades/2018-09-01-initial-schema.go
@@ -6,7 +6,7 @@ import (
 )
 
 func init() {
-	upgrades[0] = upgrade{"Initial schema", func(dialect Dialect, tx *sql.Tx) error {
+	upgrades[0] = upgrade{"Initial schema", func(dialect Dialect, tx *sql.Tx, db *sql.DB) error {
 		var byteType string
 		if dialect == SQLite {
 			byteType = "BLOB"
diff --git a/database/upgrades/2019-05-16-message-delete-cascade.go b/database/upgrades/2019-05-16-message-delete-cascade.go
index cb31cd4..131e086 100644
--- a/database/upgrades/2019-05-16-message-delete-cascade.go
+++ b/database/upgrades/2019-05-16-message-delete-cascade.go
@@ -5,7 +5,7 @@ import (
 )
 
 func init() {
-	upgrades[1] = upgrade{"Add ON DELETE CASCADE to message table", func(dialect Dialect, tx *sql.Tx) error {
+	upgrades[1] = upgrade{"Add ON DELETE CASCADE to message table", func(dialect Dialect, tx *sql.Tx, db *sql.DB) error {
 		if dialect == SQLite {
 			// SQLite doesn't support constraint updates, but it isn't that careful with constraints anyway.
 			return nil
diff --git a/database/upgrades/2019-05-21-message-timestamp-column.go b/database/upgrades/2019-05-21-message-timestamp-column.go
index b53a340..ebd7e38 100644
--- a/database/upgrades/2019-05-21-message-timestamp-column.go
+++ b/database/upgrades/2019-05-21-message-timestamp-column.go
@@ -5,7 +5,7 @@ import (
 )
 
 func init() {
-	upgrades[2] = upgrade{"Add timestamp column to messages", func(dialect Dialect, tx *sql.Tx) error {
+	upgrades[2] = upgrade{"Add timestamp column to messages", func(dialect Dialect, tx *sql.Tx, db *sql.DB) error {
 		_, err := tx.Exec("ALTER TABLE message ADD COLUMN timestamp BIGINT NOT NULL DEFAULT 0")
 		if err != nil {
 			return err
diff --git a/database/upgrades/2019-05-22-user-last-connection-column.go b/database/upgrades/2019-05-22-user-last-connection-column.go
index e53a3b8..db1a214 100644
--- a/database/upgrades/2019-05-22-user-last-connection-column.go
+++ b/database/upgrades/2019-05-22-user-last-connection-column.go
@@ -5,7 +5,7 @@ import (
 )
 
 func init() {
-	upgrades[3] = upgrade{"Add last_connection column to users", func(dialect Dialect, tx *sql.Tx) error {
+	upgrades[3] = upgrade{"Add last_connection column to users", func(dialect Dialect, tx *sql.Tx, db *sql.DB) error {
 		_, err := tx.Exec(`ALTER TABLE "user" ADD COLUMN last_connection BIGINT NOT NULL DEFAULT 0`)
 		if err != nil {
 			return err
diff --git a/database/upgrades/2019-05-23-protoupgrade.go b/database/upgrades/2019-05-23-protoupgrade.go
new file mode 100644
index 0000000..1e2d72e
--- /dev/null
+++ b/database/upgrades/2019-05-23-protoupgrade.go
@@ -0,0 +1,61 @@
+package upgrades
+
+import (
+	"database/sql"
+	"encoding/json"
+	"fmt"
+)
+
+func init() {
+	var keys = []string{"imageMessage", "contactMessage", "locationMessage", "extendedTextMessage", "documentMessage", "audioMessage", "videoMessage"}
+	upgrades[4] = upgrade{"Update message content to new protocol version", func(dialect Dialect, tx *sql.Tx, db *sql.DB) error {
+		rows, err := db.Query("SELECT mxid, content FROM message")
+		if err != nil {
+			return err
+		}
+		for rows.Next() {
+			var mxid string
+			var rawContent []byte
+			err = rows.Scan(&mxid, &rawContent)
+			if err != nil {
+				fmt.Println("Error scanning:", err)
+				continue
+			}
+			var content map[string]interface{}
+			err = json.Unmarshal(rawContent, &content)
+			if err != nil {
+				fmt.Printf("Error unmarshaling content of %s: %v\n", mxid, err)
+				continue
+			}
+
+			for _, key := range keys {
+				val, ok := content[key].(map[string]interface{})
+				if !ok {
+					continue
+				}
+				ci, ok := val["contextInfo"].(map[string]interface{})
+				if !ok {
+					continue
+				}
+				qm, ok := ci["quotedMessage"].([]interface{})
+				if !ok {
+					continue
+				}
+				ci["quotedMessage"] = qm[0]
+				goto save
+			}
+			continue
+
+		save:
+			rawContent, err = json.Marshal(&content)
+			if err != nil {
+				fmt.Printf("Error marshaling updated content of %s: %v\n", mxid, err)
+			}
+			_, err = tx.Exec("UPDATE message SET content=$1 WHERE mxid=$2", rawContent, mxid)
+			if err != nil {
+				fmt.Printf("Error updating row of %s: %v\n", mxid, err)
+			}
+		}
+		return nil
+	}}
+}
diff --git a/database/upgrades/upgrades.go b/database/upgrades/upgrades.go
index cbe3d76..5e98872 100644
--- a/database/upgrades/upgrades.go
+++ b/database/upgrades/upgrades.go
@@ -15,14 +15,14 @@ const (
 	SQLite
 )
 
-type upgradeFunc func(Dialect, *sql.Tx) error
+type upgradeFunc func(Dialect, *sql.Tx, *sql.DB) error
 
 type upgrade struct {
 	message string
 	fn upgradeFunc
 }
 
-var upgrades [4]upgrade
+var upgrades [5]upgrade
 
 func getVersion(dialect Dialect, db *sql.DB) (int, error) {
 	_, err := db.Exec("CREATE TABLE IF NOT EXISTS version (version INTEGER)")
@@ -70,7 +70,7 @@ func Run(log log.Logger, dialectName string, db *sql.DB) error {
 		if err != nil {
 			return err
 		}
-		err = upgrade.fn(dialect, tx)
+		err = upgrade.fn(dialect, tx, db)
 		if err != nil {
 			return err
 		}