I had this same issue when I upgraded to the most recent version. I went into 
the outgoing server section, left everything the way it was, but simply clicked 
on "next" so that it would check the outgoing server and once I did that, 
everything worked fine.


> -----Original Message-----
> From: [email protected] [mailto:[email protected]] On Behalf
> Of Richard
> Sent: Monday, September 29, 2014 12:02 PM
> To: [email protected]
> Subject: Re: [k-9-mail] Latest update has broken outbound SMTP SSL/TLS
> connections - completely
> 
> 
> 
> ------------ Original Message ------------
> > Date: Monday, September 29, 2014 08:29:14 -0700
> > From: Lori Cecil <[email protected]>
> > To: [email protected]
> > Subject: Re: [k-9-mail] Latest update has broken outbound SMTP
> SSL/TLS connections - completely
> >
> > Like so many others here today, I cannot send emails.  Sent you a
> > support  request and got automated response to come here.
> > Reluctantly I did and now  I am glad that I am not the only one!
> > In reply to your reply below "And  you tried re-entering the
> > password?" YES!!!!  Still no success.
> >
> > My email was as follows:
> >
> > I loved this app when I first installed it, but after today’s update I
> > am  ready to uninstall it!  I cannot send any emails (not a Gmail
> > account,  another business account).  NONE of my folders have messages
> > except the  inbox.  After “updating” my settings as the app requested,
> > I had two  accounts for the same email address, neither of which work
> > properly.  Also,  my backed up settings weren’t good enough…Just too
> > many issues!  Ready to give a bad review, but waiting until I hear
> > back.
> >
> > Please hurry!!!!!  and Thanks.
> >
> 
> 
> When making reports about sending/receiving problems (especially following an
> upgrade) I think it would be helpful if people would provide as much detail as
> possible. E.g.,
> 
> for receiving:
> 
>        protocol: imap/pop/exchange
>        security: ssl/tls / starttls / none
>            port:
>  authentication: normal password/encrypted/client certificate
> 
> 
> for sending (outgoing):
> 
>       the same as above, except that "protocol" isn't relevant
>       but add "require sign-in".
> 
> 
> I believe that with the upgrade the starttls options were tightened, which 
> may be
> causing some problems.
> 
> Previously there were two "starttls" options -- "always" and "if available". 
> If you used
> the latter there was no requirement that the server actually supported 
> starttls and as
> such your session was (or
> wasn't) encrypted based on the server-side configuration (which most people 
> don't
> know the details of or have control over).
> 
> Now where is only one "starttls" option. I haven't tested this (and I can't 
> tell explicitly
> from the release notes), but suspect that it is the previous "always" option. 
> So, if you
> use the "starttls"
> option and your server doesn't really support it, I suspect that things will 
> fail. If that's
> the case, try "none", because that's what your server has been doing all along
> anyway.
> 
> Whether you would want to continue using a service that doesn't encrypt is up 
> to you.
> 
>    - Richard
> 
> 
> 
> 
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