What precise device is the telnet coming from?
WindowsPC
What does fw ctl zdebug drop say?
@;1317998394;[cpu_2];[fw4_1];fw_log_drop_ex: Packet proto=6 DST_IP:23 -> SRC_IP:50684 dropped by fw_first_packet_state_checks Reason: First packet isn't SYN;
fw ctl zdebug+ drop
@;1317506904;[cpu_0];[SIM-209695455];do_inbound: Possible TCP state violation for <DST_IP,23,SRC_IP,50665,6> -> dropping packet ;
@;1317506904;[cpu_0];[SIM-209695455];sim_pkt_send_drop_notification: (0,0) received drop, reason: Invalid TCP option, conn: <DST_IP,23,SRC_IP,50665,6>;
@;1317506904;[cpu_0];[SIM-209695455];sim_pkt_send_drop_notification: no track is needed for this drop - not sending a notificaion, conn: <DST_IP,23,SRC_IP,50665,6>;
@;1317506904;[cpu_0];[SIM-209695455];do_packet_finish: SIMPKT_IN_DROP vsid=0, conn:<DST_IP,23,SRC_IP,50665,6>;
@;1317509016;[cpu_0];[SIM-209695455];update_tcp_state: invalid state detected (current state: 0x10000, th_flags=0x12, cdir=1) -> dropping packet, conn: [<SRC_IP,50665,DST_IP,23,6>][PPK0];
Where src_ip - windows PC and dst_ip - cisco2950.
What is noteworthy is that if the WinPC is connected through the router, without going through the Checkpoint, then the connection goes first time.
And if our WinPC connects to a cisco2960, which is located in the same network segment as the 2950, it also connects from the first time.