Hi, I have a workaround for this, but someone on stack overflow [1] suggested reporting it upstream, so here you go: I have a fancy shell prompt that executes "git rev-parse --is-inside-work-tree" to determine whether we're currently inside a working directory. This causes git to walk up the directory hierarchy looking for a containing git repo. For example, when invoked from my home directory, it stats the following paths, in order: /home/me/.git /home/me/.git/HEAD /home/me/HEAD /home /home/.git /home/.git/HEAD /home/HEAD / /.git /.git/HEAD //HEAD The last name (//HEAD) interacts badly with Cygwin, which interprets it as a UNC file share, and so demand-loads a bunch of extra DLLs and attempts to resolve/contact the server named HEAD. This obviously doesn't work too well, especially over a slow network link. I've tested with the latest Cygwin git (2.15.0); this was also present in a prior version. Cheers, Andrew [1] https://stackoverflow.com/questions/47084672