diff --git a/sys/net/route.c b/sys/net/route.c
--- a/sys/net/route.c
+++ b/sys/net/route.c
@@ -534,6 +534,41 @@
 	return (NULL);
 }
 
+/*
+ * Calculates proper ifa/ifp for the cases when gateway AF is different
+ * from dst AF.
+ *
+ * Returns 0 on success.
+ */
+__noinline static int
+rt_getifa_family(struct rt_addrinfo *info, uint32_t fibnum)
+{
+	if (info->rti_ifp == NULL) {
+		struct ifaddr *ifa = NULL;
+		/*
+		 * No transmit interface specified. Guess it by checking gw sa.
+		 */
+		const struct sockaddr *gw = info->rti_info[RTAX_GATEWAY];
+		ifa = ifa_ifwithroute(RTF_GATEWAY, gw, gw, fibnum);
+		if (ifa == NULL)
+			return (ENETUNREACH);
+		info->rti_ifp = ifa->ifa_ifp;
+	}
+
+	/* Prefer address from outgoing interface */
+	info->rti_ifa = ifaof_ifpforaddr(info->rti_info[RTAX_DST], info->rti_ifp);
+#ifdef INET
+	if (info->rti_ifa == NULL) {
+		/* Use first found IPv4 address */
+		bool loopback_ok = info->rti_ifp->if_flags & IFF_LOOPBACK;
+		info->rti_ifa = (struct ifaddr *)in_findlocal(fibnum, loopback_ok);
+	}
+#endif
+	if (info->rti_ifa == NULL)
+		return (ENETUNREACH);
+	return (0);
+}
+
 /*
  * Look up rt_addrinfo for a specific fib.
  *
@@ -566,6 +601,9 @@
 	 */
 	if (info->rti_ifa == NULL && ifaaddr != NULL)
 		info->rti_ifa = ifa_ifwithaddr(ifaaddr);
+	if ((info->rti_ifa == NULL) && ((info->rti_flags & RTF_GATEWAY) != 0) &&
+	    (gateway->sa_family != dst->sa_family))
+		return (rt_getifa_family(info, fibnum));
 	if (info->rti_ifa == NULL) {
 		const struct sockaddr *sa;
 
diff --git a/sys/netinet/in.h b/sys/netinet/in.h
--- a/sys/netinet/in.h
+++ b/sys/netinet/in.h
@@ -651,6 +651,7 @@
 int	 in_localaddr(struct in_addr);
 int	 in_localip(struct in_addr);
 int	 in_ifhasaddr(struct ifnet *, struct in_addr);
+struct in_ifaddr *in_findlocal(uint32_t, bool);
 int	 inet_aton(const char *, struct in_addr *); /* in libkern */
 char	*inet_ntoa_r(struct in_addr ina, char *buf); /* in libkern */
 char	*inet_ntop(int, const void *, char *, socklen_t); /* in libkern */
diff --git a/sys/netinet/in.c b/sys/netinet/in.c
--- a/sys/netinet/in.c
+++ b/sys/netinet/in.c
@@ -188,6 +188,40 @@
 	return (NULL);
 }
 
+/*
+ * Tries to find first IPv4 address in the provided fib.
+ * Prefers non-loopback addresses and return loopback IFF
+ * @loopback_ok is set.
+ *
+ * Returns ifa or NULL.
+ */
+struct in_ifaddr *
+in_findlocal(uint32_t fibnum, bool loopback_ok)
+{
+	struct rm_priotracker in_ifa_tracker;
+	struct in_ifaddr *ia = NULL, *ia_lo = NULL;
+
+	NET_EPOCH_ASSERT();
+
+	IN_IFADDR_RLOCK(&in_ifa_tracker);
+	CK_STAILQ_FOREACH(ia, &V_in_ifaddrhead, ia_link) {
+		uint32_t ia_fib = ia->ia_ifa.ifa_ifp->if_fib;
+		if (!V_rt_add_addr_allfibs && (fibnum != ia_fib))
+			continue;
+
+		if (!IN_LOOPBACK(ntohl(IA_SIN(ia)->sin_addr.s_addr)))
+			break;
+		if (loopback_ok)
+			ia_lo = ia;
+	}
+	IN_IFADDR_RUNLOCK(&in_ifa_tracker);
+
+	if (ia == NULL)
+		ia = ia_lo;
+
+	return (ia);
+}
+
 /*
  * Determine whether an IP address is in a reserved set of addresses
  * that may not be forwarded, or whether datagrams to that destination