I've been working on implementing SSL bumping with Squid on Cygwin. I want to inform the community that you don't need to run ./configure or recompile Squid to enable SSL bumping with Cygwin on Windows Server 2008 R2 Standard. When you install Cygwin, make sure you install the following packages: Admin Devel Net Archive Interpreters Perl Base Libs Python Database Mail Ruby Debug Math Security Shells System Tcl Utils Web You can then edit your squid.conf file to configure ssl-bumping as needed. I hope this helps some people! Derek