diff --git a/drivers/net/ovpn/peer.h b/drivers/net/ovpn/peer.h
index c0994c606554..17d57b12fa5e 100644
--- a/drivers/net/ovpn/peer.h
+++ b/drivers/net/ovpn/peer.h
@@ -46,6 +46,12 @@
  * @tcp.sk_cb.ops: pointer to the original prot_ops object (TCP only)
  * @crypto: the crypto configuration (ciphers, keys, etc..)
  * @dst_cache: cache for dst_entry used to send to peer
+ * @dst_cache_sport: inet_sport observed when the dst_cache was last
+ *		     (re-)populated; compared on every TX to detect changes
+ *		     (e.g. connect(AF_UNSPEC)) and invalidate the cache
+ * @dst_cache_mark: sk_mark observed when the dst_cache was last
+ *		    (re-)populated; compared on every TX to detect changes
+ *		    via setsockopt(SO_MARK) and invalidate the cache
  * @bind: remote peer binding
  * @keepalive_interval: seconds after which a new keepalive should be sent
  * @keepalive_xmit_exp: future timestamp when next keepalive should be sent
@@ -102,6 +108,8 @@ struct ovpn_peer {
 	} tcp;
 	struct ovpn_crypto_state crypto;
 	struct dst_cache dst_cache;
+	__be16 dst_cache_sport;
+	u32 dst_cache_mark;
 	struct ovpn_bind __rcu *bind;
 	unsigned long keepalive_interval;
 	unsigned long keepalive_xmit_exp;
diff --git a/drivers/net/ovpn/udp.c b/drivers/net/ovpn/udp.c
index 17d65d1595ed..ca502c920f54 100644
--- a/drivers/net/ovpn/udp.c
+++ b/drivers/net/ovpn/udp.c
@@ -143,7 +143,7 @@ static int ovpn_udp_encap_recv(struct sock *sk, struct sk_buff *skb)
  */
 static int ovpn_udp4_output(struct ovpn_peer *peer, struct ovpn_bind *bind,
 			    struct dst_cache *cache, struct sock *sk,
-			    struct sk_buff *skb)
+			    struct sk_buff *skb, __be16 sport, u32 mark)
 {
 	struct rtable *rt;
 	struct flowi4 fl = {
@@ -152,10 +152,10 @@ static int ovpn_udp4_output(struct ovpn_peer *peer, struct ovpn_bind *bind,
 		 */
 		.saddr = READ_ONCE(bind->local.ipv4.s_addr),
 		.daddr = bind->remote.in4.sin_addr.s_addr,
-		.fl4_sport = inet_sk(sk)->inet_sport,
+		.fl4_sport = sport,
 		.fl4_dport = bind->remote.in4.sin_port,
 		.flowi4_proto = sk->sk_protocol,
-		.flowi4_mark = sk->sk_mark,
+		.flowi4_mark = mark,
 	};
 	int ret;
 
@@ -196,7 +196,17 @@ static int ovpn_udp4_output(struct ovpn_peer *peer, struct ovpn_bind *bind,
 				    ret);
 		goto err;
 	}
-	dst_cache_set_ip4(cache, &rt->dst, fl.saddr);
+	/* only cache the result if the bind is still current: a concurrent
+	 * ovpn_peer_endpoints_update() may have replaced the bind (float) or
+	 * updated bind->local in place, in which case ovpn already reset the
+	 * cache and re-caching here would reinstate a stale route. sport/mark
+	 * are validated at TX entry by ovpn_udp_output().
+	 */
+	if (rcu_access_pointer(peer->bind) == bind &&
+	    READ_ONCE(bind->local.ipv4.s_addr) == fl.saddr)
+		dst_cache_set_ip4(cache, &rt->dst, fl.saddr);
+	else
+		dst_cache_reset(cache);
 
 transmit:
 	udp_tunnel_xmit_skb(rt, sk, skb, fl.saddr, fl.daddr, 0,
@@ -221,17 +231,18 @@ static int ovpn_udp4_output(struct ovpn_peer *peer, struct ovpn_bind *bind,
  */
 static int ovpn_udp6_output(struct ovpn_peer *peer, struct ovpn_bind *bind,
 			    struct dst_cache *cache, struct sock *sk,
-			    struct sk_buff *skb)
+			    struct sk_buff *skb, __be16 sport, u32 mark)
 {
 	struct dst_entry *dst;
+	struct in6_addr local;
 	int ret;
 
 	struct flowi6 fl = {
 		.daddr = bind->remote.in6.sin6_addr,
-		.fl6_sport = inet_sk(sk)->inet_sport,
+		.fl6_sport = sport,
 		.fl6_dport = bind->remote.in6.sin6_port,
 		.flowi6_proto = sk->sk_protocol,
-		.flowi6_mark = sk->sk_mark,
+		.flowi6_mark = mark,
 		.flowi6_oif = bind->remote.in6.sin6_scope_id,
 	};
 
@@ -267,7 +278,18 @@ static int ovpn_udp6_output(struct ovpn_peer *peer, struct ovpn_bind *bind,
 				    &bind->remote.in6, ret);
 		goto err;
 	}
-	dst_cache_set_ip6(cache, dst, &fl.saddr);
+	/* only cache the result if the bind is still current: a concurrent
+	 * ovpn_peer_endpoints_update() may have replaced the bind (float) or
+	 * updated bind->local in place, in which case ovpn already reset the
+	 * cache and re-caching here would reinstate a stale route. sport/mark
+	 * are validated at TX entry by ovpn_udp_output().
+	 */
+	ovpn_peer_local_ipv6(peer, bind, &local);
+	if (rcu_access_pointer(peer->bind) == bind &&
+	    ipv6_addr_equal(&local, &fl.saddr))
+		dst_cache_set_ip6(cache, dst, &fl.saddr);
+	else
+		dst_cache_reset(cache);
 
 transmit:
 	/* user IPv6 packets may be larger than the transport interface
@@ -306,12 +328,40 @@ static int ovpn_udp_output(struct ovpn_peer *peer, struct dst_cache *cache,
 			   struct sock *sk, struct sk_buff *skb)
 {
 	struct ovpn_bind *bind;
+	__be16 sport;
+	u32 mark;
 	int ret;
 
 	/* set sk to null if skb is already orphaned */
 	if (!skb->destructor)
 		skb->sk = NULL;
 
+	sport = READ_ONCE(inet_sk(sk)->inet_sport);
+	if (unlikely(!sport)) {
+		/* the transport UDP socket has been disconnected (e.g. via
+		 * connect(AF_UNSPEC)): inet_sport == 0 means the socket has
+		 * been unhashed and sending from source port 0 is nonsense;
+		 * refuse and tell the operator
+		 */
+		netdev_warn_once(peer->ovpn->dev,
+				 "UDP transport socket has no source port; was it disconnected?\n");
+		return -EIO;
+	}
+	mark = READ_ONCE(sk->sk_mark);
+
+	/* userspace can change sk_mark (via setsockopt(SO_MARK)) and
+	 * inet_sport (via connect(AF_UNSPEC)) at any time without notifying
+	 * ovpn; if either differs from what the dst_cache was last populated
+	 * with, invalidate the cache now so a hit doesn't return a dst
+	 * resolved with the old value
+	 */
+	if (READ_ONCE(peer->dst_cache_sport) != sport ||
+	    READ_ONCE(peer->dst_cache_mark) != mark) {
+		dst_cache_reset(cache);
+		WRITE_ONCE(peer->dst_cache_sport, sport);
+		WRITE_ONCE(peer->dst_cache_mark, mark);
+	}
+
 	rcu_read_lock();
 	bind = rcu_dereference(peer->bind);
 	if (unlikely(!bind)) {
@@ -323,11 +373,11 @@ static int ovpn_udp_output(struct ovpn_peer *peer, struct dst_cache *cache,
 
 	switch (bind->remote.in4.sin_family) {
 	case AF_INET:
-		ret = ovpn_udp4_output(peer, bind, cache, sk, skb);
+		ret = ovpn_udp4_output(peer, bind, cache, sk, skb, sport, mark);
 		break;
 #if IS_ENABLED(CONFIG_IPV6)
 	case AF_INET6:
-		ret = ovpn_udp6_output(peer, bind, cache, sk, skb);
+		ret = ovpn_udp6_output(peer, bind, cache, sk, skb, sport, mark);
 		break;
 #endif
 	default:
