diff --git a/irc/client.go b/irc/client.go
index 5ce22b44..aa0a6e52 100644
--- a/irc/client.go
+++ b/irc/client.go
@@ -1398,7 +1398,7 @@ func (client *Client) destroy(session *Session) {
 
 	// alert monitors
 	if registered {
-		client.server.monitorManager.AlertAbout(details.nick, details.nickCasefolded, false)
+		client.server.monitorManager.AlertAbout(details.nick, details.nickCasefolded, false, nil)
 	}
 
 	// clean up channels
diff --git a/irc/monitor.go b/irc/monitor.go
index 9131e81b..46ab46e6 100644
--- a/irc/monitor.go
+++ b/irc/monitor.go
@@ -38,7 +38,7 @@ func (manager *MonitorManager) AddMonitors(users utils.HashSet[*Session], cfnick
 }
 
 // AlertAbout alerts everyone monitoring `client`'s nick that `client` is now {on,off}line.
-func (manager *MonitorManager) AlertAbout(nick, cfnick string, online bool) {
+func (manager *MonitorManager) AlertAbout(nick, cfnick string, online bool, client *Client) {
 	var watchers []*Session
 	// safely copy the list of clients watching our nick
 	manager.RLock()
@@ -52,8 +52,21 @@ func (manager *MonitorManager) AlertAbout(nick, cfnick string, online bool) {
 		command = RPL_MONONLINE
 	}
 
+	var metadata map[string]string
+	if online && client != nil {
+		metadata = client.ListMetadata()
+	}
+
 	for _, session := range watchers {
 		session.Send(nil, session.client.server.name, command, session.client.Nick(), nick)
+
+		if metadata != nil && session.capabilities.Has(caps.Metadata) {
+			for key := range session.MetadataSubscriptions() {
+				if val, ok := metadata[key]; ok {
+					session.Send(nil, client.server.name, "METADATA", nick, key, "*", val)
+				}
+			}
+		}
 	}
 }
 
diff --git a/irc/nickname.go b/irc/nickname.go
index 0f2f8232..28781fff 100644
--- a/irc/nickname.go
+++ b/irc/nickname.go
@@ -128,9 +128,11 @@ func performNickChange(server *Server, client *Client, target *Client, session *
 	}
 
 	newCfnick := target.NickCasefolded()
-	if newCfnick != details.nickCasefolded {
-		client.server.monitorManager.AlertAbout(details.nick, details.nickCasefolded, false)
-		client.server.monitorManager.AlertAbout(assignedNickname, newCfnick, true)
+	// send MONITOR updates only for nick changes, not for new connection registration;
+	// defer MONITOR for new connection registration until pre-registration metadata is applied
+	if hadNick && newCfnick != details.nickCasefolded {
+		client.server.monitorManager.AlertAbout(details.nick, details.nickCasefolded, false, nil)
+		client.server.monitorManager.AlertAbout(assignedNickname, newCfnick, true, target)
 	}
 	return nil
 }
diff --git a/irc/server.go b/irc/server.go
index c59ac571..d1cf736e 100644
--- a/irc/server.go
+++ b/irc/server.go
@@ -430,6 +430,8 @@ func (server *Server) tryRegister(c *Client, session *Session) (exiting bool) {
 
 	c.applyPreregMetadata(session)
 
+	c.server.monitorManager.AlertAbout(c.Nick(), c.NickCasefolded(), true, c)
+
 	// this is not a reattach, so if the client is always-on, this is the first time
 	// the Client object was created during the current server uptime. mark dirty in
 	// order to persist the realname and the user modes: