diff --git a/config/upgrade.go b/config/upgrade.go
index 8338105..ff3d22c 100644
--- a/config/upgrade.go
+++ b/config/upgrade.go
@@ -17,8 +17,8 @@
 package config
 
 import (
-	"maunium.net/go/mautrix/appservice"
 	"maunium.net/go/mautrix/bridge/bridgeconfig"
+	"maunium.net/go/mautrix/util"
 	up "maunium.net/go/mautrix/util/configupgrade"
 )
 
@@ -61,7 +61,7 @@ func DoUpgrade(helper *up.Helper) {
 
 	helper.Copy(up.Str, "bridge", "provisioning", "prefix")
 	if secret, ok := helper.Get(up.Str, "bridge", "provisioning", "shared_secret"); !ok || secret == "generate" {
-		sharedSecret := appservice.RandomString(64)
+		sharedSecret := util.RandomString(64)
 		helper.Set(up.Str, sharedSecret, "bridge", "provisioning", "shared_secret")
 	} else {
 		helper.Copy(up.Str, "bridge", "provisioning", "shared_secret")
diff --git a/database/database.go b/database/database.go
index 34aca2d..1b69d7e 100644
--- a/database/database.go
+++ b/database/database.go
@@ -5,6 +5,7 @@ import (
 
 	_ "github.com/lib/pq"
 	_ "github.com/mattn/go-sqlite3"
+	"maunium.net/go/maulogger/v2"
 
 	"maunium.net/go/mautrix/util/dbutil"
 
@@ -25,44 +26,44 @@ type Database struct {
 	Role     *RoleQuery
 }
 
-func New(baseDB *dbutil.Database) *Database {
+func New(baseDB *dbutil.Database, log maulogger.Logger) *Database {
 	db := &Database{Database: baseDB}
 	db.UpgradeTable = upgrades.Table
 	db.User = &UserQuery{
 		db:  db,
-		log: db.Log.Sub("User"),
+		log: log.Sub("User"),
 	}
 	db.Portal = &PortalQuery{
 		db:  db,
-		log: db.Log.Sub("Portal"),
+		log: log.Sub("Portal"),
 	}
 	db.Puppet = &PuppetQuery{
 		db:  db,
-		log: db.Log.Sub("Puppet"),
+		log: log.Sub("Puppet"),
 	}
 	db.Message = &MessageQuery{
 		db:  db,
-		log: db.Log.Sub("Message"),
+		log: log.Sub("Message"),
 	}
 	db.Thread = &ThreadQuery{
 		db:  db,
-		log: db.Log.Sub("Thread"),
+		log: log.Sub("Thread"),
 	}
 	db.Reaction = &ReactionQuery{
 		db:  db,
-		log: db.Log.Sub("Reaction"),
+		log: log.Sub("Reaction"),
 	}
 	db.Emoji = &EmojiQuery{
 		db:  db,
-		log: db.Log.Sub("Emoji"),
+		log: log.Sub("Emoji"),
 	}
 	db.Guild = &GuildQuery{
 		db:  db,
-		log: db.Log.Sub("Guild"),
+		log: log.Sub("Guild"),
 	}
 	db.Role = &RoleQuery{
 		db:  db,
-		log: db.Log.Sub("Role"),
+		log: log.Sub("Role"),
 	}
 	return db
 }
diff --git a/go.mod b/go.mod
index cf44d26..72731f5 100644
--- a/go.mod
+++ b/go.mod
@@ -11,10 +11,13 @@ require (
 	github.com/skip2/go-qrcode v0.0.0-20200617195104-da1b6568686e
 	github.com/yuin/goldmark v1.4.12
 	maunium.net/go/maulogger/v2 v2.3.2
-	maunium.net/go/mautrix v0.11.1-0.20220708142125-1f795238d635
+	maunium.net/go/mautrix v0.11.1-0.20220815133425-ba1fce8fce24
 )
 
 require (
+	github.com/mattn/go-colorable v0.1.12 // indirect
+	github.com/mattn/go-isatty v0.0.14 // indirect
+	github.com/rs/zerolog v1.27.0 // indirect
 	github.com/tidwall/gjson v1.14.1 // indirect
 	github.com/tidwall/match v1.1.1 // indirect
 	github.com/tidwall/pretty v1.2.0 // indirect
diff --git a/go.sum b/go.sum
index ed68b1a..b61b07e 100644
--- a/go.sum
+++ b/go.sum
@@ -1,6 +1,10 @@
+github.com/DATA-DOG/go-sqlmock v1.5.0 h1:Shsta01QNfFxHCfpW6YH2STWB0MudeXXEWMr20OEh60=
+github.com/DATA-DOG/go-sqlmock v1.5.0/go.mod h1:f/Ixk793poVmq4qj/V1dPUg2JEAKC73Q5eFN3EC/SaM=
+github.com/coreos/go-systemd/v22 v22.3.3-0.20220203105225-a9a7ef127534/go.mod h1:Y58oyj3AT4RCenI/lSvhwexgC+NSVTIJ3seZv2GcEnc=
 github.com/davecgh/go-spew v1.1.0/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
 github.com/davecgh/go-spew v1.1.1 h1:vj9j/u1bqnvCEfJOwUhtlOARqs3+rkHYY13jYWTU97c=
 github.com/davecgh/go-spew v1.1.1/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
+github.com/godbus/dbus/v5 v5.0.4/go.mod h1:xhWf0FNVPg57R7Z0UbKHbJfkEywrmjJnf7w5xrFpKfA=
 github.com/gorilla/mux v1.8.0 h1:i40aqfkR1h2SlN9hojwV5ZA91wcXFOvkdNIeFDP5koI=
 github.com/gorilla/mux v1.8.0/go.mod h1:DVbg23sWSpFRCP0SfiEN6jmj59UnW/n46BH5rLB71So=
 github.com/gorilla/websocket v1.4.2/go.mod h1:YR8l580nyteQvAITg2hZ9XVh4b55+EU/adAjf1fMHhE=
@@ -8,10 +12,18 @@ github.com/gorilla/websocket v1.5.0 h1:PPwGk2jz7EePpoHN/+ClbZu8SPxiqlu12wZP/3sWm
 github.com/gorilla/websocket v1.5.0/go.mod h1:YR8l580nyteQvAITg2hZ9XVh4b55+EU/adAjf1fMHhE=
 github.com/lib/pq v1.10.6 h1:jbk+ZieJ0D7EVGJYpL9QTz7/YW6UHbmdnZWYyK5cdBs=
 github.com/lib/pq v1.10.6/go.mod h1:AlVN5x4E4T544tWzH6hKfbfQvm3HdbOxrmggDNAPY9o=
+github.com/mattn/go-colorable v0.1.12 h1:jF+Du6AlPIjs2BiUiQlKOX0rt3SujHxPnksPKZbaA40=
+github.com/mattn/go-colorable v0.1.12/go.mod h1:u5H1YNBxpqRaxsYJYSkiCWKzEfiAb1Gb520KVy5xxl4=
+github.com/mattn/go-isatty v0.0.14 h1:yVuAays6BHfxijgZPzw+3Zlu5yQgKGP2/hcQbHb7S9Y=
+github.com/mattn/go-isatty v0.0.14/go.mod h1:7GGIvUiUoEMVVmxf/4nioHXj79iQHKdU27kJ6hsGG94=
 github.com/mattn/go-sqlite3 v1.14.14 h1:qZgc/Rwetq+MtyE18WhzjokPD93dNqLGNT3QJuLvBGw=
 github.com/mattn/go-sqlite3 v1.14.14/go.mod h1:NyWgC/yNuGj7Q9rpYnZvas74GogHl5/Z4A/KQRfk6bU=
+github.com/pkg/errors v0.9.1/go.mod h1:bwawxfHBFNV+L2hUp1rHADufV3IMtnDRdf1r5NINEl0=
 github.com/pmezard/go-difflib v1.0.0 h1:4DBwDE0NGyQoBHbLQYPwSUPoCMWR5BEzIk/f1lZbAQM=
 github.com/pmezard/go-difflib v1.0.0/go.mod h1:iKH77koFhYxTK1pcRnkKkqfTogsbg7gZNVY4sRDYZ/4=
+github.com/rs/xid v1.3.0/go.mod h1:trrq9SKmegXys3aeAKXMUTdJsYXVwGY3RLcfgqegfbg=
+github.com/rs/zerolog v1.27.0 h1:1T7qCieN22GVc8S4Q2yuexzBb1EqjbgjSH9RohbMjKs=
+github.com/rs/zerolog v1.27.0/go.mod h1:7frBqO0oezxmnO7GF86FY++uy8I0Tk/If5ni1G9Qc0U=
 github.com/skip2/go-qrcode v0.0.0-20200617195104-da1b6568686e h1:MRM5ITcdelLK2j1vwZ3Je0FKVCfqOLp5zO6trqMLYs0=
 github.com/skip2/go-qrcode v0.0.0-20200617195104-da1b6568686e/go.mod h1:XV66xRDqSt+GTGFMVlhk3ULuV0y9ZmzeVGR4mloJI3M=
 github.com/stretchr/objx v0.1.0/go.mod h1:HFkY916IF+rwdDfMAkV7OtwuqBVzrE8GR6GFx+wExME=
@@ -42,6 +54,8 @@ golang.org/x/net v0.0.0-20220624214902-1bab6f366d9e/go.mod h1:XRhObCWvk6IyKnWLug
 golang.org/x/sys v0.0.0-20201119102817-f84b799fce68/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20210423082822-04245dca01da/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20210615035016-665e8c7367d1/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
+golang.org/x/sys v0.0.0-20210630005230-0f9fa26af87c/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
+golang.org/x/sys v0.0.0-20210927094055-39ccf1dd6fa6/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.0.0-20220520151302-bc2c85ada10a h1:dGzPydgVsqGcTRVwiLJ1jVbufYwmzD3LfVPLKsKg+0k=
 golang.org/x/sys v0.0.0-20220520151302-bc2c85ada10a/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
@@ -59,5 +73,5 @@ 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 v0.11.1-0.20220708142125-1f795238d635 h1:/kbw/ZW+MzViciUoTmhJoasmZcqHhcKSPws+FfKwb0s=
-maunium.net/go/mautrix v0.11.1-0.20220708142125-1f795238d635/go.mod h1:85mjebfgKX7jjca7XNKTt7lHueX3YQsFUU+5o/FxpTw=
+maunium.net/go/mautrix v0.11.1-0.20220815133425-ba1fce8fce24 h1:40cxOxHwTw+UYdDTV//tHw9bjNMmJ9uH6ye+C1SbOGA=
+maunium.net/go/mautrix v0.11.1-0.20220815133425-ba1fce8fce24/go.mod h1:hHvNi5iKVAiI2MAdAeXHtP4g9BvNEX2rsQpSF/x6Kx4=
diff --git a/main.go b/main.go
index 2d2dccd..c707e3d 100644
--- a/main.go
+++ b/main.go
@@ -88,7 +88,7 @@ func (br *DiscordBridge) Init() {
 	br.CommandProcessor = commands.NewProcessor(&br.Bridge)
 	br.RegisterCommands()
 
-	br.DB = database.New(br.Bridge.DB)
+	br.DB = database.New(br.Bridge.DB, br.Log.Sub("Database"))
 	discordLog = br.Log.Sub("Discord")
 }
 
diff --git a/portal.go b/portal.go
index f162046..ee61331 100644
--- a/portal.go
+++ b/portal.go
@@ -9,6 +9,7 @@ import (
 	"sync"
 	"time"
 
+	"maunium.net/go/mautrix/bridge/status"
 	"maunium.net/go/mautrix/crypto/attachment"
 	"maunium.net/go/mautrix/util/variationselector"
 
@@ -984,7 +985,7 @@ var (
 	errUnknownEmoji                = errors.New("unknown emoji")
 )
 
-func errorToStatusReason(err error) (reason event.MessageStatusReason, isCertain, canRetry, sendNotice bool) {
+func errorToStatusReason(err error) (reason event.MessageStatusReason, status event.MessageStatus, isCertain, sendNotice bool, humanMessage string) {
 	switch {
 	case errors.Is(err, errUnknownMsgType),
 		errors.Is(err, errUnknownRelationType),
@@ -993,19 +994,19 @@ func errorToStatusReason(err error) (reason event.MessageStatusReason, isCertain
 		errors.Is(err, id.InvalidContentURI),
 		errors.Is(err, attachment.UnsupportedVersion),
 		errors.Is(err, attachment.UnsupportedAlgorithm):
-		return event.MessageStatusUnsupported, true, false, true
+		return event.MessageStatusUnsupported, event.MessageStatusFail, true, true, ""
 	case errors.Is(err, attachment.HashMismatch),
 		errors.Is(err, attachment.InvalidKey),
 		errors.Is(err, attachment.InvalidInitVector):
-		return event.MessageStatusUndecryptable, true, false, true
+		return event.MessageStatusUndecryptable, event.MessageStatusFail, true, true, ""
 	case errors.Is(err, errUserNotReceiver):
-		return event.MessageStatusNoPermission, true, false, false
+		return event.MessageStatusNoPermission, event.MessageStatusFail, true, false, ""
 	case errors.Is(err, errUnknownEditTarget):
-		return event.MessageStatusGenericError, true, false, false
+		return event.MessageStatusGenericError, event.MessageStatusFail, true, false, ""
 	case errors.Is(err, errTargetNotFound):
-		return event.MessageStatusGenericError, true, false, true
+		return event.MessageStatusGenericError, event.MessageStatusFail, true, true, ""
 	default:
-		return event.MessageStatusGenericError, false, true, true
+		return event.MessageStatusGenericError, event.MessageStatusRetriable, false, true, ""
 	}
 }
 
@@ -1025,13 +1026,12 @@ func (portal *Portal) sendStatusEvent(evtID id.EventID, err error) {
 			Type:    event.RelReference,
 			EventID: evtID,
 		},
-		Success: err == nil,
+		Status: event.MessageStatusSuccess,
 	}
-	if !content.Success {
-		reason, isCertain, canRetry, _ := errorToStatusReason(err)
-		content.Reason = reason
-		content.IsCertain = &isCertain
-		content.CanRetry = &canRetry
+	if err == nil {
+		content.Status = event.MessageStatusSuccess
+	} else {
+		content.Reason, content.Status, _, _, content.Message = errorToStatusReason(err)
 		content.Error = err.Error()
 	}
 	_, err = intent.SendMessageEvent(portal.MXID, event.BeeperMessageStatus, &content)
@@ -1062,9 +1062,9 @@ func (portal *Portal) sendMessageMetrics(evt *event.Event, err error, part strin
 			level = log.LevelDebug
 		}
 		portal.log.Logfln(level, "%s %s %s from %s: %v", part, msgType, evtDescription, evt.Sender, err)
-		reason, isCertain, _, sendNotice := errorToStatusReason(err)
-		status := bridge.ReasonToCheckpointStatus(reason)
-		portal.bridge.SendMessageCheckpoint(evt, bridge.MsgStepRemote, err, status, 0)
+		reason, statusCode, isCertain, sendNotice, _ := errorToStatusReason(err)
+		checkpointStatus := status.ReasonToCheckpointStatus(reason, statusCode)
+		portal.bridge.SendMessageCheckpoint(evt, status.MsgStepRemote, err, checkpointStatus, 0)
 		if sendNotice {
 			portal.sendErrorMessage(msgType, err.Error(), isCertain)
 		}
@@ -1072,7 +1072,7 @@ func (portal *Portal) sendMessageMetrics(evt *event.Event, err error, part strin
 	} else {
 		portal.log.Debugfln("Handled Matrix %s %s", msgType, evtDescription)
 		portal.sendDeliveryReceipt(evt.ID)
-		portal.bridge.SendMessageSuccessCheckpoint(evt, bridge.MsgStepRemote, 0)
+		portal.bridge.SendMessageSuccessCheckpoint(evt, status.MsgStepRemote, 0)
 		portal.sendStatusEvent(evt.ID, nil)
 	}
 }
diff --git a/user.go b/user.go
index 2c36db4..09490cb 100644
--- a/user.go
+++ b/user.go
@@ -19,6 +19,7 @@ import (
 	"maunium.net/go/mautrix/appservice"
 	"maunium.net/go/mautrix/bridge"
 	"maunium.net/go/mautrix/bridge/bridgeconfig"
+	"maunium.net/go/mautrix/bridge/status"
 	"maunium.net/go/mautrix/event"
 	"maunium.net/go/mautrix/id"
 
@@ -215,22 +216,22 @@ func (br *DiscordBridge) startUsers() {
 	usersWithToken := br.getAllUsersWithToken()
 	for _, u := range usersWithToken {
 		go func(user *User) {
-			user.BridgeState.Send(bridge.State{StateEvent: bridge.StateConnecting})
+			user.BridgeState.Send(status.BridgeState{StateEvent: status.StateConnecting})
 			err := user.Connect()
 			if err != nil {
 				user.log.Errorfln("Error connecting: %v", err)
 				if closeErr := (&websocket.CloseError{}); errors.As(err, &closeErr) && closeErr.Code == 4004 {
-					user.BridgeState.Send(bridge.State{StateEvent: bridge.StateBadCredentials, Message: err.Error()})
+					user.BridgeState.Send(status.BridgeState{StateEvent: status.StateBadCredentials, Message: err.Error()})
 					user.DiscordToken = ""
 					user.Update()
 				} else {
-					user.BridgeState.Send(bridge.State{StateEvent: bridge.StateUnknownError, Message: err.Error()})
+					user.BridgeState.Send(status.BridgeState{StateEvent: status.StateUnknownError, Message: err.Error()})
 				}
 			}
 		}(u)
 	}
 	if len(usersWithToken) == 0 {
-		br.SendGlobalBridgeState(bridge.State{StateEvent: bridge.StateUnconfigured}.Fill(nil))
+		br.SendGlobalBridgeState(status.BridgeState{StateEvent: status.StateUnconfigured}.Fill(nil))
 	}
 
 	br.Log.Debugln("Starting custom puppets")
@@ -530,7 +531,7 @@ func (user *User) readyHandler(_ *discordgo.Session, r *discordgo.Ready) {
 		user.DiscordID = r.User.ID
 		user.Update()
 	}
-	user.BridgeState.Send(bridge.State{StateEvent: bridge.StateBackfilling})
+	user.BridgeState.Send(status.BridgeState{StateEvent: status.StateBackfilling})
 
 	updateTS := time.Now()
 	portalsInSpace := make(map[string]bool)
@@ -558,7 +559,7 @@ func (user *User) readyHandler(_ *discordgo.Session, r *discordgo.Ready) {
 		user.Update()
 	}
 
-	user.BridgeState.Send(bridge.State{StateEvent: bridge.StateConnected})
+	user.BridgeState.Send(status.BridgeState{StateEvent: status.StateConnected})
 }
 
 func (user *User) addPrivateChannelToSpace(portal *Portal) bool {
@@ -706,14 +707,14 @@ func (user *User) connectedHandler(_ *discordgo.Session, c *discordgo.Connect) {
 	user.log.Debugln("Connected to discord")
 
 	user.tryAutomaticDoublePuppeting()
-	if user.BridgeState.GetPrev().StateEvent == bridge.StateTransientDisconnect {
-		user.BridgeState.Send(bridge.State{StateEvent: bridge.StateConnected})
+	if user.BridgeState.GetPrev().StateEvent == status.StateTransientDisconnect {
+		user.BridgeState.Send(status.BridgeState{StateEvent: status.StateConnected})
 	}
 }
 
 func (user *User) disconnectedHandler(_ *discordgo.Session, d *discordgo.Disconnect) {
 	user.log.Debugln("Disconnected from discord")
-	user.BridgeState.Send(bridge.State{StateEvent: bridge.StateTransientDisconnect})
+	user.BridgeState.Send(status.BridgeState{StateEvent: status.StateTransientDisconnect})
 }
 
 func (user *User) guildCreateHandler(_ *discordgo.Session, g *discordgo.GuildCreate) {