Well I could not myself (from my notes) last time I tried. cpan deps tells us a 25% chance and possibly close to 0 on cygwin. One of my pet projects is making a strawberry-like dist. for cygwin and I keep notes on possible inclusions and problems. Anyway the last time I tried libssh2 was not a cygwin package, so it could be the situation has got better. I use cygwin and cygperl daily but my environment is frozen. I will give it a try at home later in the latest cygwin environment.

First you need yo make sure your cygwin environment has enough packages to be actually able to compile C. For this make sure that the output of the command ' cygcheck -c' does have gcc and gcc-core, (g)make, and does NOT have any incomplete. If something is missing use the standard cygwin setup to install the missing parts.

You also need the external C library libssh2 which was recently packaged in cygwin. So add it to your setup list.

The 'as' error above seems to imply you are using cygwin perl. Which version are you using 5.8.8 or 5.10.0.