diff --git a/pkg/connector/backfill.go b/pkg/connector/backfill.go
index b23de03..b589098 100644
--- a/pkg/connector/backfill.go
+++ b/pkg/connector/backfill.go
@@ -61,6 +61,7 @@ func (dc *DiscordClient) FetchMessages(ctx context.Context, fetchParams bridgev2
 	log.Debug().Msg("Fetching channel history for backfill")
 	msgs, err := dc.Session.ChannelMessages(channelID, count, beforeID, afterID, "")
 	if err != nil {
+		dc.handlePossible40002(err)
 		return nil, err
 	}
 
diff --git a/pkg/connector/bridge_state.go b/pkg/connector/bridge_state.go
index d1ccad1..bd21f86 100644
--- a/pkg/connector/bridge_state.go
+++ b/pkg/connector/bridge_state.go
@@ -17,26 +17,30 @@
 package connector
 
 import (
+	"errors"
 	"time"
 
+	"github.com/bwmarrin/discordgo"
 	"maunium.net/go/mautrix/bridgev2/status"
 )
 
 const (
-	DiscordNotLoggedIn   status.BridgeStateErrorCode = "discord-not-logged-in"
-	DiscordInvalidAuth   status.BridgeStateErrorCode = "discord-invalid-auth"
-	DiscordDisconnected  status.BridgeStateErrorCode = "discord-disconnected"
-	DiscordConnectFailed status.BridgeStateErrorCode = "discord-connect-failed"
+	DiscordNotLoggedIn         status.BridgeStateErrorCode = "dc-not-logged-in"
+	DiscordTransientDisconnect status.BridgeStateErrorCode = "dc-transient-disconnect"
+	DiscordInvalidAuth         status.BridgeStateErrorCode = "dc-websocket-disconnect-4004"
+	DiscordHTTP40002           status.BridgeStateErrorCode = "dc-http-40002"
+	DiscordUnknownWebsocketErr status.BridgeStateErrorCode = "dc-unknown-websocket-error"
 )
 
 const discordDisconnectDebounce = 7 * time.Second
 
 func init() {
 	status.BridgeStateHumanErrors.Update(status.BridgeStateErrorMap{
-		DiscordNotLoggedIn:   "You're not logged into Discord. Relogin to continue using the bridge.",
-		DiscordInvalidAuth:   "You were logged out of Discord. Relogin to continue using the bridge.",
-		DiscordDisconnected:  "Disconnected from Discord. Trying to reconnect.",
-		DiscordConnectFailed: "Connecting to Discord failed.",
+		DiscordNotLoggedIn:         "You're not logged into Discord. Relogin to continue using the bridge.",
+		DiscordTransientDisconnect: "Temporarily disconnected from Discord, trying to reconnect.",
+		DiscordInvalidAuth:         "Discord access token is no longer valid, please log in again.",
+		DiscordHTTP40002:           "Discord requires a verified account, please verify and log in again.",
+		DiscordUnknownWebsocketErr: "Unknown Discord websocket error.",
 	})
 }
 
@@ -79,6 +83,7 @@ func (d *DiscordClient) markInvalidAuth(message string) {
 		StateEvent: status.StateBadCredentials,
 		Error:      DiscordInvalidAuth,
 		Message:    message,
+		UserAction: status.UserActionRelogin,
 	})
 }
 
@@ -105,23 +110,44 @@ func (d *DiscordClient) scheduleTransientDisconnect(message string) {
 		}
 		login.BridgeState.Send(status.BridgeState{
 			StateEvent: status.StateTransientDisconnect,
-			Error:      DiscordDisconnected,
+			Error:      DiscordTransientDisconnect,
 			Message:    message,
 		})
 	})
 	d.bridgeStateLock.Unlock()
 }
 
-func (d *DiscordClient) sendConnectFailure(err error) {
+func (d *DiscordClient) sendConnectFailure(err error, final bool) {
 	if d.UserLogin == nil || err == nil {
 		return
 	}
+	stateEvent := status.StateTransientDisconnect
+	if final {
+		stateEvent = status.StateUnknownError
+	}
 	d.UserLogin.BridgeState.Send(status.BridgeState{
-		StateEvent: status.StateUnknownError,
-		Error:      DiscordConnectFailed,
+		StateEvent: stateEvent,
+		Error:      DiscordUnknownWebsocketErr,
 		Message:    err.Error(),
 		Info: map[string]any{
 			"go_error": err.Error(),
 		},
 	})
 }
+
+func (d *DiscordClient) handlePossible40002(err error) bool {
+	var restErr *discordgo.RESTError
+	if !errors.As(err, &restErr) || restErr.Message == nil || restErr.Message.Code != discordgo.ErrCodeActionRequiredVerifiedAccount {
+		return false
+	}
+	if d.UserLogin == nil {
+		return true
+	}
+	d.UserLogin.BridgeState.Send(status.BridgeState{
+		StateEvent: status.StateBadCredentials,
+		Error:      DiscordHTTP40002,
+		Message:    restErr.Message.Message,
+		UserAction: status.UserActionRelogin,
+	})
+	return true
+}
diff --git a/pkg/connector/client.go b/pkg/connector/client.go
index 2dd4b8d..0c81dd4 100644
--- a/pkg/connector/client.go
+++ b/pkg/connector/client.go
@@ -110,6 +110,7 @@ func (d *DiscordClient) Connect(ctx context.Context) {
 		d.UserLogin.BridgeState.Send(status.BridgeState{
 			StateEvent: status.StateBadCredentials,
 			Error:      DiscordNotLoggedIn,
+			UserAction: status.UserActionRelogin,
 		})
 		return
 	}
@@ -117,9 +118,7 @@ func (d *DiscordClient) Connect(ctx context.Context) {
 	d.UserLogin.BridgeState.Send(status.BridgeState{
 		StateEvent: status.StateConnecting,
 	})
-	if err := d.connect(ctx); err != nil {
-		log.Err(err).Msg("Couldn't connect to Discord")
-	}
+	d.connectWithRetry(ctx, 0)
 }
 
 func (cl *DiscordClient) handleDiscordEventSync(event any) {
@@ -140,7 +139,6 @@ func (cl *DiscordClient) connect(ctx context.Context) error {
 	}
 	if err != nil {
 		log.Err(err).Msg("Failed to connect to Discord")
-		cl.sendConnectFailure(err)
 		return err
 	}
 
@@ -148,7 +146,6 @@ func (cl *DiscordClient) connect(ctx context.Context) error {
 	if !cl.IsLoggedIn() {
 		err := fmt.Errorf("unknown identity even after connecting to Discord")
 		log.Err(err).Msg("No Discord user available after connecting")
-		cl.sendConnectFailure(err)
 		return err
 	}
 	user := cl.Session.State.User
@@ -170,6 +167,27 @@ func (cl *DiscordClient) connect(ctx context.Context) error {
 	return nil
 }
 
+func (d *DiscordClient) connectWithRetry(ctx context.Context, retryCount int) {
+	err := d.connect(ctx)
+	if err == nil || ctx.Err() != nil {
+		return
+	}
+	if retryCount < 6 {
+		d.sendConnectFailure(err, false)
+		retryInSeconds := 2 << retryCount
+		zerolog.Ctx(ctx).Debug().Int("retry_in_seconds", retryInSeconds).Msg("Sleeping and retrying connection")
+		select {
+		case <-time.After(time.Duration(retryInSeconds) * time.Second):
+		case <-ctx.Done():
+			zerolog.Ctx(ctx).Info().Msg("Context canceled, exiting connect retry loop")
+			return
+		}
+		d.connectWithRetry(ctx, retryCount+1)
+	} else {
+		d.sendConnectFailure(err, true)
+	}
+}
+
 func (d *DiscordClient) Disconnect() {
 	d.UserLogin.Log.Info().Msg("Disconnecting session")
 	d.Session.Close()
@@ -398,6 +416,7 @@ func (d *DiscordClient) bridgeGuild(ctx context.Context, guildID string) error {
 		Threads:    true,
 	})
 	if err != nil {
+		d.handlePossible40002(err)
 		log.Warn().Err(err).Msg("Failed to subscribe to guild; proceeding")
 	}
 
diff --git a/pkg/connector/handlematrix.go b/pkg/connector/handlematrix.go
index bc2d50f..2449fa9 100644
--- a/pkg/connector/handlematrix.go
+++ b/pkg/connector/handlematrix.go
@@ -56,6 +56,7 @@ func (d *DiscordClient) HandleMatrixMessage(ctx context.Context, msg *bridgev2.M
 
 	sentMsg, err := d.Session.ChannelMessageSendComplex(discordid.ParsePortalID(msg.Portal.ID), sendReq, options...)
 	if err != nil {
+		d.handlePossible40002(err)
 		return nil, err
 	}
 	sentMsgTimestamp, _ := discordgo.SnowflakeTimestamp(sentMsg.ID)
@@ -90,6 +91,9 @@ func (d *DiscordClient) HandleMatrixReaction(ctx context.Context, reaction *brid
 	meta := portal.Metadata.(*discordid.PortalMetadata)
 
 	err := d.Session.MessageReactionAddUser(meta.GuildID, discordid.ParsePortalID(portal.ID), discordid.ParseMessageID(reaction.TargetMessage.ID), relatesToKey)
+	if err != nil {
+		d.handlePossible40002(err)
+	}
 	return nil, err
 }
 
@@ -100,13 +104,20 @@ func (d *DiscordClient) HandleMatrixReactionRemove(ctx context.Context, removal
 	guildID := removal.Portal.Metadata.(*discordid.PortalMetadata).GuildID
 
 	err := d.Session.MessageReactionRemoveUser(guildID, channelID, discordid.ParseMessageID(removing.MessageID), discordid.ParseEmojiID(emojiID), discordid.ParseUserLoginID(d.UserLogin.ID))
+	if err != nil {
+		d.handlePossible40002(err)
+	}
 	return err
 }
 
 func (d *DiscordClient) HandleMatrixMessageRemove(ctx context.Context, removal *bridgev2.MatrixMessageRemove) error {
 	channelID := discordid.ParsePortalID(removal.Portal.ID)
 	messageID := discordid.ParseMessageID(removal.TargetMessage.ID)
-	return d.Session.ChannelMessageDelete(channelID, messageID)
+	err := d.Session.ChannelMessageDelete(channelID, messageID)
+	if err != nil {
+		d.handlePossible40002(err)
+	}
+	return err
 }
 
 func (d *DiscordClient) HandleMatrixReadReceipt(ctx context.Context, msg *bridgev2.MatrixReadReceipt) error {
@@ -153,6 +164,7 @@ func (d *DiscordClient) HandleMatrixReadReceipt(ctx context.Context, msg *bridge
 	channelID := discordid.ParsePortalID(msg.Portal.ID)
 	resp, err := d.Session.ChannelMessageAckNoToken(channelID, targetMessageID, discordgo.WithChannelReferer(guildID, channelID))
 	if err != nil {
+		d.handlePossible40002(err)
 		log.Err(err).Msg("Failed to send read receipt to Discord")
 		return err
 	} else if resp.Token != nil {
@@ -186,6 +198,7 @@ func (d *DiscordClient) viewingChannel(ctx context.Context, portal *bridgev2.Por
 		err := d.Session.MarkViewing(channelID)
 
 		if err != nil {
+			d.handlePossible40002(err)
 			log.Error().Err(err).Msg("Failed to mark user as viewing channel")
 			return err
 		}
@@ -211,6 +224,7 @@ func (d *DiscordClient) HandleMatrixTyping(ctx context.Context, msg *bridgev2.Ma
 	err := d.Session.ChannelTyping(channelID, discordgo.WithChannelReferer(guildID, channelID))
 
 	if err != nil {
+		d.handlePossible40002(err)
 		log.Warn().Err(err).Msg("Failed to mark user as typing")
 		return err
 	}