If you need an SSL-proxy connection via squid on Debian/Linux you need to recompile the squid-2.7 package with --enable-ssl option.
Here a short step by step tutorial how to rebuild a squid .deb package with --enable-ssl option.
Enable source repository on your buildmachine. To describe it in words what we will do is downloading the source packages where the original package of squid in the Debian distribution is build from and rebuild this sources with the activated ssl option to get an self build .deb file which you can install on your Debian machine. This procedure works for the most Debian packages the same way not just for squid.
for example add:
deb-src http://ftp.de.debian.org/debian lenny main contrib non-free deb-src http://backports.debian.org/debian-backports lenny-backports main contrib non-free deb-src http://volatile.debian.org/debian-volatile/ lenny/volatile main contrib non-free
change directory to /usr/src:
download squid sources:
apt-get source squid
download squid build dependencies:
apt-get build-dep squid
download sources for openssh:
apt-get build-dep openssh
download sources for openssl:
apt-get build-dep openssl
download and install necessary stuff for build process:
apt-get install devscripts build-essential fakeroot
edit the build rules and add the --enable-ssl option to the configure section:
configure the new options (don't do a make or make install !!!) :
compile and build package:
debuild -us -uc -b