SSH if command output is more than about 5 lines

Solution 1:

sounds like a wired MTU issue. slightly...

is it possible that you have jumboframes enabled? probably not. anyway - try setting lower mtu on the debian and see if it helps.

Solution 2:

There's probably a problem with the MTU of your network connection - when the Linux server attempts to send too many bytes of data in a single network packet, probably the router is refusing to forward it to the windows box, because it thinks the packet size is too large to send over the wireless network. You should be able to reduce the MTU for the Ethernet interface on the linux box, and this would probably solve your problem.

To diagnose, try ping -s <packetsize> <windows-ip> from the linux box to the IP of your windows machine, and ping <linux-ip> <packetsize> from the windows box to linux, with different values for the packetsize parameter, and see if the maximum size is different in either direction.

Also: man ping on linux will be helpful for understanding what's going on.