diff --git a/packet.c b/packet.c
index 2df7a97b7..1c781763c 100644
--- a/packet.c
+++ b/packet.c
@@ -1,4 +1,4 @@
-/* $OpenBSD: packet.c,v 1.328 2025/12/30 00:22:58 djm Exp $ */
+/* $OpenBSD: packet.c,v 1.329 2025/12/30 00:35:37 djm Exp $ */
 /*
  * Author: Tatu Ylonen <ylo@cs.hut.fi>
  * Copyright (c) 1995 Tatu Ylonen <ylo@cs.hut.fi>, Espoo, Finland
@@ -1118,10 +1118,6 @@ ssh_packet_need_rekeying(struct ssh *ssh, u_int outbound_packet_len)
 	if (ssh_packet_is_rekeying(ssh))
 		return 0;
 
-	/* Peer can't rekey */
-	if (ssh->compat & SSH_BUG_NOREKEY)
-		return 0;
-
 	/*
 	 * Permit one packet in or out per rekey - this allows us to
 	 * make progress when rekey limits are very small.
@@ -1368,8 +1364,7 @@ ssh_packet_send2_wrapped(struct ssh *ssh)
 		logit("outgoing seqnr wraps around");
 	}
 	if (++state->p_send.packets == 0)
-		if (!(ssh->compat & SSH_BUG_NOREKEY))
-			return SSH_ERR_NEED_REKEY;
+		return SSH_ERR_NEED_REKEY;
 	state->p_send.blocks += len / block_size;
 	state->p_send.bytes += len;
 	sshbuf_reset(state->outgoing_packet);
@@ -1784,8 +1779,7 @@ ssh_packet_read_poll2(struct ssh *ssh, u_char *typep, u_int32_t *seqnr_p)
 		logit("incoming seqnr wraps around");
 	}
 	if (++state->p_read.packets == 0)
-		if (!(ssh->compat & SSH_BUG_NOREKEY))
-			return SSH_ERR_NEED_REKEY;
+		return SSH_ERR_NEED_REKEY;
 	state->p_read.blocks += (state->packlen + 4) / block_size;
 	state->p_read.bytes += state->packlen + 4;
 
diff --git a/sshconnect.c b/sshconnect.c
index 4b4a90189..9dd1d02ea 100644
--- a/sshconnect.c
+++ b/sshconnect.c
@@ -1,4 +1,4 @@
-/* $OpenBSD: sshconnect.c,v 1.377 2025/12/22 01:49:03 djm Exp $ */
+/* $OpenBSD: sshconnect.c,v 1.378 2025/12/30 00:35:37 djm Exp $ */
 /*
  * Author: Tatu Ylonen <ylo@cs.hut.fi>
  * Copyright (c) 1995 Tatu Ylonen <ylo@cs.hut.fi>, Espoo, Finland
@@ -44,6 +44,7 @@
 #include "xmalloc.h"
 #include "hostfile.h"
 #include "ssh.h"
+#include "compat.h"
 #include "sshbuf.h"
 #include "packet.h"
 #include "sshkey.h"
@@ -1609,6 +1610,11 @@ ssh_login(struct ssh *ssh, Sensitive *sensitive, const char *orighost,
 	    options.version_addendum)) != 0)
 		sshpkt_fatal(ssh, r, "banner exchange");
 
+	if ((ssh->compat & SSH_BUG_NOREKEY)) {
+		logit("Warning: this server does not support rekeying.");
+		logit("This session will eventually fail");
+	}
+
 	/* Put the connection into non-blocking mode. */
 	ssh_packet_set_nonblocking(ssh);
 
diff --git a/sshd-session.c b/sshd-session.c
index 5d384fa2f..5f34f6444 100644
--- a/sshd-session.c
+++ b/sshd-session.c
@@ -1,4 +1,4 @@
-/* $OpenBSD: sshd-session.c,v 1.18 2025/12/16 08:32:50 dtucker Exp $ */
+/* $OpenBSD: sshd-session.c,v 1.19 2025/12/30 00:35:37 djm Exp $ */
 /*
  * SSH2 implementation:
  * Privilege Separation:
@@ -1252,6 +1252,9 @@ main(int ac, char **av)
 	    options.version_addendum)) != 0)
 		sshpkt_fatal(ssh, r, "banner exchange");
 
+	if ((ssh->compat & SSH_BUG_NOREKEY))
+		debug("client does not support rekeying");
+
 	ssh_packet_set_nonblocking(ssh);
 
 	/* allocate authentication context */