Setting my fears finally aside, I embarked three days ago on switching my mail over to Gmail, accessed over IMAP. A couple of polemical points:

• If you think “webmail” is a real mail interface, please stop reading right now.
• If you use POP, for whatever reason, then consider this: you have no technical reason to do so and every technical reason not to do so and use IMAP instead. And if Yahoo does not support IMAP that just gave you one more reason to abandon Yahoo and go to a real service. Heck, even AOL has been supporting IMAP access for a while now. Anyway, it costs you a few bucks a year to setup your own IMAP server on some host, so unless you are my granpda I don’t want to hear your excuses. ;-)

With that out of the way… I confess that Google’s IMAP support got me excited — here is a company that I generally respect and whose developers I trust (especially since some of them are good friends of mine)! And Google Apps for Domains is a neat service. It was, therefore, a not too troublesome decision to point one of my domains to Google Apps and funnel all my email to an account on that domain.

Next, I setup Apple’s Mail (often called Mail.app on the Interwebs, in order to give it a somewhat distinguishable name) with a new IMAP account pointed at my Gmail domain account. Right off the bat, problems ensued. The IMAP connection succeeded (and continues to succeed) only intermittently. It does not connect at all from my work where I tunnel out through an SSH SOCKS proxy. And Google’s recommendation that I not store my “Sent” messages on the server is a bit disconcerting. And did I mention its slow?

The problem with the connection over SOCKS pretty much ends the trial for me, but I admit that is a bit of an esoteric need, and further it is entirely valid to suspect that the problem with the SOCKS proxied access lies elsewhere (not at Google). YMMV, and all that. But you should also consider this from Wired:

IMAP, YouMAP, WeMAP: Mail Protocol’s Proponents Argue for Better Support

With Gmail’s adoption of IMAP, one of electronic messaging’s best-kept secrets has been thrust suddenly into the spotlight. But IMAP’s inventor says the move, while overdue, doesn’t deserve the fanfare it received.

Mark Crispin, an often outspoken purist when it comes to e-mail implementations, had a typically-for-him dubious reaction to the announcement of Gmail’s added support for his protocol.

“I am very pleased that Gmail intends to adopt IMAP,” he says. (Note his word choice: “intends.”) “I feel that their current server should be considered to be a ‘work in progress’ and not as a viable ‘ready for prime time’ IMAP server.”

Crispin says if he were to rate Google’s current implementation of IMAP, it would be “quite damning.”

I haven’t quite given up on Google yet… tomorrow I shall continue my investigation of the SOCKS strangeness. If I get to the bottom of it, I will post an update.