Hello,

On Wed, Jun 20, 2012 at 06:24:37PM -0700, jeremy
bentham wrote:
> I found by experimenting that imap works as well
> as pop: if I start an imap session before I try
> to send an e-mail, I can send; otherwise I
> can't.

I think that POP-before-SMTP and IMAP-before-SMTP
should work just fine regardless of POP/IMAP
connection status (active/closed). So this stuff
is irrelevant.

> from my .pinerc
...
> incoming-folders=Mail/[]
> eski {mail.eskimo.com/ssl/novalidate-cert}mail/today

As I understand, mail.eskimo.com/ssl translates to
smtp_url="smtps://[email protected]:465", i.e.
it's SSL from the beginning, not STARTTLS, and
it's served on port 465, not 587 or 25.

Hope this helps,

-- 
With best regards,
xrgtn

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