diff --git a/sys/netinet/tcp_input.c b/sys/netinet/tcp_input.c
--- a/sys/netinet/tcp_input.c
+++ b/sys/netinet/tcp_input.c
@@ -3022,6 +3022,7 @@
 				 * we'll hang forever.
 				 */
 				if (so->so_rcv.sb_state & SBS_CANTRCVMORE) {
+					tcp_free_sackholes(tp);
 					soisdisconnected(so);
 					tcp_timer_activate(tp, TT_2MSL,
 					    (tcp_fast_finwait2_recycle ?
diff --git a/sys/netinet/tcp_subr.c b/sys/netinet/tcp_subr.c
--- a/sys/netinet/tcp_subr.c
+++ b/sys/netinet/tcp_subr.c
@@ -2383,6 +2383,7 @@
 #endif
 
 	INP_WLOCK_ASSERT(inp);
+	MPASS(TAILQ_EMPTY(&tp->snd_holes));
 
 	tcp_timer_stop(tp);
 
@@ -2394,9 +2395,6 @@
 	if (tp->t_flags & TF_TOE)
 		tcp_offload_detach(tp);
 #endif
-
-	tcp_free_sackholes(tp);
-
 #ifdef TCPPCAP
 	/* Free the TCP PCAP queues. */
 	tcp_pcap_drain(&(tp->t_inpkts));
@@ -2531,6 +2529,7 @@
 	if (tp->t_state != TCPS_CLOSED)
 		tcp_state_change(tp, TCPS_CLOSED);
 	KASSERT(inp->inp_socket != NULL, ("tcp_close: inp_socket NULL"));
+	tcp_free_sackholes(tp);
 	soisdisconnected(so);
 	if (inp->inp_flags & INP_SOCKREF) {
 		inp->inp_flags &= ~INP_SOCKREF;
diff --git a/sys/netinet/tcp_timewait.c b/sys/netinet/tcp_timewait.c
--- a/sys/netinet/tcp_timewait.c
+++ b/sys/netinet/tcp_timewait.c
@@ -119,6 +119,7 @@
 	    "(inp->inp_flags & INP_DROPPED) != 0"));
 
 	tcp_state_change(tp, TCPS_TIME_WAIT);
+	tcp_free_sackholes(tp);
 	soisdisconnected(inp->inp_socket);
 
 	if (tp->t_flags & TF_ACKNOW)
diff --git a/sys/netinet/tcp_usrreq.c b/sys/netinet/tcp_usrreq.c
--- a/sys/netinet/tcp_usrreq.c
+++ b/sys/netinet/tcp_usrreq.c
@@ -2777,6 +2777,7 @@
 	if (tp->t_acktime == 0)
 		tp->t_acktime = ticks;
 	if (tp->t_state >= TCPS_FIN_WAIT_2) {
+		tcp_free_sackholes(tp);
 		soisdisconnected(tptosocket(tp));
 		/* Prevent the connection hanging in FIN_WAIT_2 forever. */
 		if (tp->t_state == TCPS_FIN_WAIT_2) {