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From: Simon Josefsson <jas@extundo.com>
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Subject: Re: Mac OS X smtpmail "encryption too weak"
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Gilbert Harman <harman@Princeton.EDU> writes:

> On 10/26/02 6:49 AM, "Simon Josefsson" <jas@extundo.com> wrote:
>
>> If you frob `smtpmail-debug-info', how do the trace buffer look?  Is
>> STARTTLS activated? Are authentication used?  Do you know exactly what
>> the server requires, in terms of security level?
>
> I don't know how to answer your last question.  This is what the trace
> buffer looks like, after "pleased to meet you":
>
> 250-ENHANCEDSTATUSCODES
> 250-PIPELINING
> 250-EXPN
> 250-VERB
> 250-8BITMIME
> 250-SIZE 12288000
> 250-DSN
> 250-ETRN
> 250-AUTH LOGIN PLAIN
> 250-STARTTLS
> 250-DELIVERBY
> 250 HELP
> MAIL FROM: <harman@princeton.edu> SIZE=318
> 503 5.7.0 encryption too weak 0 less than 39
> QUIT

It seems no STARTTLS nor authentication took place (and this is
probably why the server complains).  Are you sure the configuration is
correct?  Have you installed the external STARTTLS binary?  It is
required for STARTTLS.