[Pkg-exim4-users] How to get around "Must issue a STARTTLS command first"

[Marc Haber]

On Sat, Jul 31, 2010 at 10:12:28PM +0900, Norbert Preining wrote:
> On Fr, 30 Jul 2010, Marc Haber wrote:
> > On Fri, Jul 30, 2010 at 06:04:29PM +0900, Norbert Preining wrote:
> > > I am running Debian/sid with exim4 and when trying to deliver 
> > > emails to the local smtp server I get
> > > 	Must issue a STARTTLS command first
> > > Now on some Debian/Exim pages I found the cryptic comment
> > > (from http://pkg-exim4.alioth.debian.org/README/README.Debian.etch.html#TLS)
> > > 	TLS on connect is not natively supported.
> > > Are these two things related?
> > > Is there a way to fix that?
> > 
> > What exactly are you trying to do?
> 
> As I said, I am trying to deliver emails to the smtp server of my
> university as it is my ISP.
> 
> I have set in
> 	/etc/exim4/conf.d/main/000_localmacros
> 
> DCsmarthost=smtp.host.foo.bar::587
> 
> (actually I have a lookup into /etc/smarthost with
> ${lookup{*}lsearch{/etc/smarthost}{$value:}{}}
> plus a fall back)
> 
> but any time exim tries to send an email out via that smtp I get an 
> error message telling me
> 
> ...
>   590885 at bugs.debian.org
>     SMTP error from remote mail server after MAIL FROM:<preining at logic.at>
> SIZE=2963:
>     host XXXXXXXXXX [NN.NN.NN.NN]: 530 Must issue a STARTTLS command
> first

Please don't obfuscate. It is not security relevant which server
you're trying to authenticate to. Even worse, by obfuscating, you have
deprived me of the possibility of trying whether the server correctly
advertises its capabilities, making it harder for me to help you and
delaying your result.

> Is that clearer, or do you need more information? Other than that I 
> haven't changed anything (as far as I remmeber) from default exim4 
> split config setup (receiving email, sending out via smarthost).

Try 
echo foo | exim -d mh+pkg-exim4-users at zugschlus.de
and send the output to the list. Exim will asterisk out the password,
so there is no private data in the debug output.

Greetings
Marc

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