diff --git a/upstream.go b/upstream.go
index 8dc71d5..dd3afce 100644
--- a/upstream.go
+++ b/upstream.go
@@ -153,6 +153,10 @@ type upstreamConn struct {
 	// been sent yet.
 	pendingCmds map[string][]pendingUpstreamCommand
 
+	pendingRegainNick string
+	regainNickTimer   *time.Timer
+	regainNickBackoff *backoffer
+
 	gotMotd bool
 }
 
@@ -869,6 +873,13 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			// Ignore the initial MOTD upon connection, but forward
 			// subsequent MOTD messages downstream
 			uc.gotMotd = true
+
+			// If the server doesn't support MONITOR, periodically try to
+			// regain our desired nick
+			if _, ok := uc.isupport["MONITOR"]; !ok {
+				uc.startRegainNickTimer()
+			}
+
 			return nil
 		}
 
@@ -924,6 +935,11 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			uc.logger.Printf("changed nick from %q to %q", uc.nick, newNick)
 			me = true
 			uc.nick = newNick
+
+			if uc.network.equalCasemap(uc.pendingRegainNick, newNick) {
+				uc.pendingRegainNick = ""
+				uc.stopRegainNickTimer()
+			}
 		}
 
 		uc.channels.ForEach(func(ch *upstreamChannel) {
@@ -1773,6 +1789,18 @@ func (uc *upstreamConn) handleMessage(ctx context.Context, msg *irc.Message) err
 			})
 			return nil
 		}
+
+		var failedNick string
+		if err := parseMessageParams(msg, nil, &failedNick); err != nil {
+			return err
+		}
+		if uc.network.equalCasemap(uc.pendingRegainNick, failedNick) {
+			// This message comes from our own logic to try to regain our
+			// desired nick, don't relay to downstream connections
+			uc.pendingRegainNick = ""
+			return nil
+		}
+
 		fallthrough
 	case irc.ERR_PASSWDMISMATCH, irc.ERR_ERRONEUSNICKNAME, irc.ERR_NICKCOLLISION, irc.ERR_UNAVAILRESOURCE, irc.ERR_NOPERMFORHOST, irc.ERR_YOUREBANNEDCREEP:
 		if !uc.registered {
@@ -2238,3 +2266,67 @@ func (uc *upstreamConn) updateMonitor() {
 		uc.monitored.Del(target)
 	}
 }
+
+func (uc *upstreamConn) stopRegainNickTimer() {
+	if uc.regainNickTimer != nil {
+		uc.regainNickTimer.Stop()
+		// Maybe we're racing with the timer goroutine, so maybe we'll receive
+		// an eventTryRegainNick later on, but tryRegainNick handles that case
+	}
+	uc.regainNickTimer = nil
+	uc.regainNickBackoff = nil
+}
+
+func (uc *upstreamConn) startRegainNickTimer() {
+	if uc.regainNickBackoff != nil || uc.regainNickTimer != nil {
+		panic("startRegainNickTimer called twice")
+	}
+
+	wantNick := database.GetNick(&uc.user.User, &uc.network.Network)
+	if uc.isOurNick(wantNick) {
+		return
+	}
+
+	const (
+		min    = 15 * time.Second
+		max    = 10 * time.Minute
+		jitter = 10 * time.Second
+	)
+	uc.regainNickBackoff = newBackoffer(min, max, jitter)
+	uc.regainNickTimer = time.AfterFunc(uc.regainNickBackoff.Next(), func() {
+		e := eventTryRegainNick{uc: uc, nick: wantNick}
+		select {
+		case uc.network.user.events <- e:
+			// ok
+		default:
+			uc.logger.Printf("skipping nick regain attempt: event queue is full")
+		}
+	})
+}
+
+func (uc *upstreamConn) tryRegainNick(nick string) {
+	ctx := context.TODO()
+
+	if uc.regainNickTimer == nil {
+		return
+	}
+
+	// Maybe the user has updated their desired nick
+	wantNick := database.GetNick(&uc.user.User, &uc.network.Network)
+	if wantNick != nick || uc.isOurNick(wantNick) {
+		uc.stopRegainNickTimer()
+		return
+	}
+
+	uc.regainNickTimer.Reset(uc.regainNickBackoff.Next())
+
+	if uc.pendingRegainNick != "" {
+		return
+	}
+
+	uc.SendMessage(ctx, &irc.Message{
+		Command: "NICK",
+		Params:  []string{wantNick},
+	})
+	uc.pendingRegainNick = wantNick
+}
diff --git a/user.go b/user.go
index 7e22c45..8c072f5 100644
--- a/user.go
+++ b/user.go
@@ -75,6 +75,11 @@ type eventUserUpdate struct {
 	done     chan error
 }
 
+type eventTryRegainNick struct {
+	uc   *upstreamConn
+	nick string
+}
+
 type deliveredClientMap map[string]string // client name -> msg ID
 
 type deliveredStore struct {
@@ -755,6 +760,8 @@ func (u *user) run() {
 					dc.Close()
 				}
 			}
+		case eventTryRegainNick:
+			e.uc.tryRegainNick(e.nick)
 		case eventStop:
 			for _, dc := range u.downstreamConns {
 				dc.Close()
@@ -776,6 +783,7 @@ func (u *user) run() {
 func (u *user) handleUpstreamDisconnected(uc *upstreamConn) {
 	uc.network.conn = nil
 
+	uc.stopRegainNickTimer()
 	uc.abortPendingCommands()
 
 	uc.channels.ForEach(func(uch *upstreamChannel) {