I did have OCSP and CRL (in the certificates pane of the Keychain Access preferences) both set to “Best Attempt”. Turning these both off made the delays stop.

It seems the OCSP server (revealed in the cert details) for my email cert is unreachable at the moment.

I turned this back on, opened the Mail Activity Viewer window, and hit the new message button. It hangs of course, but there’s no clue in the activity viewer what it’s doing. It would be nice to have a hint there like “Checking user@host cert: waiting for ocsp.ca.org”.

But the post seems to assume that my concern is of a tin-foil hat conspiracy nature. I hope it make it plain in my post that this is not the case.

I am more concerned about Mail not obeying my proxy settings and thus rendering itself unusable for over a minute everytime I tried to reply to a message. And about the difficulty of finding a fix for the problem.

Mac Geekery responds to this or clarifies this misunderstanding. Worth a look if you haven’t seen it.

http://www.macgeekery.com/tips/mail_app_doesnt_phone_home_either

@Adrian - That would make sense to me if the email I was replying to had come from a .Mac account or if I was using a .Mac account to reply to it. But I was using my work account to reply to any email sent from another user at work.

@Dave - I don’t know enough to have an opinion :) But unchecking the option in Keychain’s preferences seems preferable. I can’t test until I am in at work tomorrow, but checking it is what creates the com.apple.security.plist file in the first place. So it looks promising.

I wonder, are there any repercussions to deleting the com.apple.security.plist file besides getting rid of that cert lookup issue? I’m hesitant to delete an Apple plist that has the word ’security’ in it.

Here that philosophy gets undermined. I am not as smart about these things as Scott, Rui, JC, Adrian and (obviously) Alan are, but I am not clueless either.

There is no way that I could have debugged this problen without Tim’s help and the help of a handful of others who are “in the know”. I would have faced this 30 second to one minute delay in using Mail in perpetuity.

That simply seems like bad usability design to me, something for which Apple is otherwise justly famous.

Nor do I really understand why Mail ignored my proxy settings and didn’t route the request through the proxied port, which would have prevented the problem arising in the first place.