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TLS over various client connections

I am trying to determine capabilities of different clients my customers
may be using so that I can provide the necessary instructions.

For Ximian Evolution, I had to 'allow bind_v2' to get it to work at all,
but it still does not work using TLS. I have version 1.2.2 and all the
settings seem to suggest it should work using TLS since it is an option,
but I just get 'Can't connect...'.

For Outlook Express, I am not sure if I'll even need a secure connection
using this software because I don't see how anyone can do anything but
read, not write. Nevertheless, I cannot get TLS to work by selecting the
option in Version 6 to use a secure connection. When checking that box,
it sets the port to 636, I have tried it over both ports and nothing.

Just looking to the list here to see if anyone has dealt with either of
these programs and can provide insight on their capabilities or provide
a link to some info?