It appears that whenever you set up a new mail account on Mac Mail (or on iPhone etc), that as soon as you enter the server and the mail account password, Mac Mail tries to connect to the mail server. However this connection occurs before you can set the SSL option. So it looks like the initial connection transmits the mail account password as plain text.
It looks to me like all Apple devices (i.e. iPhones, iPads, Mac Computers) use basically the same process, and appear to make an initial connection to the mail server without using SSL.
This seems like a very insecure configuration. If this is happening then this is a pretty major security flaw. It would mean that users of Mac Mail applications could easily have their mail passwords read by their ISPs or anyone else (???) who had access to the line during that set up phase.
Apart from not using Apple products there is a way around it, but I think 99.9% of people are not going to realize this is happening. On OS X you can choose a different Mail App, but I don't think that is an option on iPhones, iPads etc. So potentially this might mean 100s of millions of people using mail on an Apple products have transmitted their mail passwords in plain text at some point.
Anyone running Wire Shark or something similar able verify this is happening?