Have you ever face the problem of frequent disconnection in a huge LAN say 4,5 routers between you have the internal gateway?
I kindda faced this problem, Pidgin (specially XMPP based) was timing out every now and then, VoIP calls were being disconnected, SSH session terminal session used and hang and what not. I didn’t know where the exact problem was so i googled, asked on irc and came across mtr.
You can install it using
apt-get install install mtr
or with aptitude, or any GUI tool of your choice.
What i did was i started a terminator window, divided a tab into 4 workspaces e.g. 1 for my local WLAN router, one for internal gateway, one for gateway of ISP and one with a hostname say yahoo, then ranmtr in console mode by using -t switch and gave it respective hostnames. Now i have a single terminator tab showing packet loss against all four and i kept it running for like couple of hours and checked where exactly were packets being lost. In my case i had to implement QoS to give high priority to 22, 5060 and 5223 ports in routers.
mtr has a lot of useful switches, try man mtr for more.