On 24 Jun 2012, at 21:20, Christian Rößner wrote:

>>> I have an interesting problem: I am building dovecot packages for Ubuntu 
>>> since 10.04. Never had bigger trouble with it. Now since 2.1.6 or 2.1.7 (I 
>>> can not say more precisely), Thunderbird 10ESR and Outlook 2010 can no 
>>> longer use 143/TLS correctly. Automx delvers 143/TLS and Outlook tells me 
>>> that it can not create a secure connection. I changed automx to use 993/SSL 
>>> and everything works. Under Thunderbird 10ESR, I get a box that tells me 
>>> that I need to change settings. When I sent mail, TB told me that it could 
>>> not copy the mail to the sent folder. I also changed to 993/SSL and 
>>> everything is perfect.
>>> 
>>> At the other and, Apples Mail.app and iOS devices work perfectly over 
>>> 143/TLS. So my guess is that it has to do with OpenSSL. Did something 
>>> change in dovecot concerning TLS? Can I change options in the built process?
>> 
>> What was the Dovecot version you were using previously which worked?
> 
> I am not sure which version worked. My best guess is 2.1.4 or 2.1.5, because 
> I skipped 2.1.6. But 2.1.6 has the same issues, as my friend Uwe did report 
> the same issues with that one.
> 
> @Robert: I am talking about Ubuntu 10.04, so this can not be a problem with 
> openssl itself, as that did not change

I've seen problems with all kinds of clients and servers, even with Dovecot 1.x 
where TLS/Auto settings fail and I simply always instruct end users to 
explicitly choose 993/SSL to get a good TLS connection reliably.

It seems like it might not be so version-specific or even anything wrong at the 
server end.

James.

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