diff --git a/handshake_manager.go b/handshake_manager.go
index b246aa48..b4bebdc7 100644
--- a/handshake_manager.go
+++ b/handshake_manager.go
@@ -295,7 +295,13 @@ func (hm *HandshakeManager) handleOutbound(vpnIp netip.Addr, lighthouseTriggered
 		hm.messageMetrics.Tx(header.Handshake, hh.machine.Subtype(), 1)
 		err := hm.outside.WriteTo(stage0, addr)
 		if err != nil {
-			hostinfo.logger(hm.l).Error("Failed to send handshake message",
+			// These repeat every attempt, so match the success log below and only shout when the remotes changed
+			level := slog.LevelDebug
+			if remotesHaveChanged {
+				level = slog.LevelError
+			}
+
+			hostinfo.logger(hm.l).Log(context.Background(), level, "Failed to send handshake message",
 				"udpAddr", addr,
 				"initiatorIndex", hostinfo.localIndexId,
 				"handshake", hsFields,
diff --git a/inside.go b/inside.go
index 163a6034..a80b2e96 100644
--- a/inside.go
+++ b/inside.go
@@ -408,7 +408,7 @@ func (f *Interface) sendNoMetrics(t header.MessageType, st header.MessageSubType
 		if err != nil {
 			hostinfo.logger(f.l).Error("Failed to write outgoing packet",
 				"error", err,
-				"udpAddr", remote,
+				"udpAddr", hr,
 			)
 		}
 	} else {