Index: head/sys/netinet/tcp_input.c
===================================================================
--- head/sys/netinet/tcp_input.c
+++ head/sys/netinet/tcp_input.c
@@ -1682,6 +1682,9 @@
 		to.to_tsecr -= tp->ts_offset;
 		if (TSTMP_GT(to.to_tsecr, tcp_ts_getticks()))
 			to.to_tsecr = 0;
+		else if (tp->t_flags & TF_PREVVALID &&
+			 tp->t_badrxtwin != 0 && SEQ_LT(to.to_tsecr, tp->t_badrxtwin))
+			cc_cong_signal(tp, th, CC_RTO_ERR);
 	}
 	/*
 	 * Process options only when we get SYN/ACK back. The SYN case
@@ -1794,9 +1797,10 @@
 				TCPSTAT_INC(tcps_predack);
 
 				/*
-				 * "bad retransmit" recovery.
+				 * "bad retransmit" recovery without timestamps.
 				 */
-				if (tp->t_rxtshift == 1 &&
+				if ((to.to_flags & TOF_TS) == 0 &&
+				    tp->t_rxtshift == 1 &&
 				    tp->t_flags & TF_PREVVALID &&
 				    (int)(ticks - tp->t_badrxtwin) < 0) {
 					cc_cong_signal(tp, th, CC_RTO_ERR);
@@ -2787,8 +2791,10 @@
 		 * original cwnd and ssthresh, and proceed to transmit where
 		 * we left off.
 		 */
-		if (tp->t_rxtshift == 1 && tp->t_flags & TF_PREVVALID &&
-		    (int)(ticks - tp->t_badrxtwin) < 0)
+		if (tp->t_rxtshift == 1 &&
+		    tp->t_flags & TF_PREVVALID &&
+		    tp->t_badrxtwin &&
+		    SEQ_LT(to.to_tsecr, tp->t_badrxtwin))
 			cc_cong_signal(tp, th, CC_RTO_ERR);
 
 		/*
Index: head/sys/netinet/tcp_output.c
===================================================================
--- head/sys/netinet/tcp_output.c
+++ head/sys/netinet/tcp_output.c
@@ -206,7 +206,7 @@
 #if defined(IPSEC) || defined(IPSEC_SUPPORT)
 	unsigned ipsec_optlen = 0;
 #endif
-	int idle, sendalot;
+	int idle, sendalot, curticks;
 	int sack_rxmit, sack_bytes_rxmt;
 	struct sackhole *p;
 	int tso, mtu;
@@ -808,9 +808,12 @@
 		/* Timestamps. */
 		if ((tp->t_flags & TF_RCVD_TSTMP) ||
 		    ((flags & TH_SYN) && (tp->t_flags & TF_REQ_TSTMP))) {
-			to.to_tsval = tcp_ts_getticks() + tp->ts_offset;
+			curticks = tcp_ts_getticks();
+			to.to_tsval = curticks + tp->ts_offset;
 			to.to_tsecr = tp->ts_recent;
 			to.to_flags |= TOF_TS;
+			if (tp->t_rxtshift == 1)
+				tp->t_badrxtwin = curticks;
 		}
 
 		/* Set receive buffer autosizing timestamp. */
Index: head/sys/netinet/tcp_timer.c
===================================================================
--- head/sys/netinet/tcp_timer.c
+++ head/sys/netinet/tcp_timer.c
@@ -693,7 +693,12 @@
 			tp->t_flags |= TF_WASCRECOVERY;
 		else
 			tp->t_flags &= ~TF_WASCRECOVERY;
-		tp->t_badrxtwin = ticks + (tp->t_srtt >> (TCP_RTT_SHIFT + 1));
+		if ((tp->t_flags & TF_RCVD_TSTMP) == 0)
+			tp->t_badrxtwin = ticks + (tp->t_srtt >> (TCP_RTT_SHIFT + 1));
+		/* In the event that we've negotiated timestamps
+		 * badrxtwin will be set to the value that we set
+		 * the retransmitted packet's to_tsval to by tcp_output
+		 */
 		tp->t_flags |= TF_PREVVALID;
 	} else
 		tp->t_flags &= ~TF_PREVVALID;