I did watch my maillog, and I see a single esmtp connect with nothing after 
ward but a flood of successful imap traffic from the same IP.  So I downloaded 
FlexMail4 for the WM6 platform, it had no issues (in fact this mail is from my 
mobile).

The cert is what it was, a self created one using the fields ~ gave it in the 
config.  Pocket Outlook has done this to me a few times before... Silently quit 
doing whatever it used to do... I suspect that if i looked at turning logging 
on auth and esmtp
I could see a bit more.. But FlexMail4 has shown me a much nicer client... I 
can even use an IMAP folder for my sent mail so it's all kept in one central 
place...

Nick

-- sent from blackjack 2 --
Nick Ellson
CCIE# 20018
"Educating Layer 8, one user at a time."

------- Original Message -------
From: Gordon Messmer <[email protected]>
To: [email protected]
Sent: 2/1/2009, 12:26:35 AM
Subject: Re: [courier-users] Pocket IE stopped sending through ESMTP?

Nick Ellson wrote:
> I have what appears to be a working Courier smtp/imap pair that I use with 
> my Windows Mobile Phone to send and recieve mail. I use the built in 
> Pocket Outlook and just two days ago my system stopped sending any mail 
> (from the handheld to Courier) but seems to be doing fine with IMAP 
> recieving mail. I know my Courier setup is unchanged, and seems to work 
> with my local PINE and Evolution clients.

Use "tail -f /var/log/maillog" to see if you get a new connection to the 
SMTP server when the client tries to send an email.  If you see a 
connection, watch for errors.

> So I am just hoping someone might have seen this before or can help me up 
> the logging to try and determine why? (I am wondering about the self 
> signed certs, and if WM6.1 just decided that they are now untrusted for 
> sending mail? ;)

Use openssl to check the certificate:

openssl s_client -connect smtp.example.com:465 -crlf

or for STARTTLS:

openssl s_client -connect smtp.example.com:25 -starttls smtp -crlf


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