Hi Brendan,

thanks very much for these suggestions.

On 19 Sep 2010, at 22:43, Brendan Cully wrote:
>> If your mutt was built with --enable-debug (mutt -v will include the
>> line +DEBUG if so), you can run mutt -d2 to get a trace of mutt's
>> conversation with the SMTP server in ~/.muttdebug0. There should be
>> more clues in there.

I've rebuilt (and upgraded from 1.5.20 to 1.5.21). Here's the log. I don't see 
anything unusual.

2010-09-19 23:14:38] Sending message...
[2010-09-19 23:14:38] Looking up mail.physics.ox.ac.uk...
[2010-09-19 23:14:38] Connecting to mail.physics.ox.ac.uk...
[2010-09-19 23:14:38] Connected to mail.physics.ox.ac.uk:587 on fd=6
[2010-09-19 23:14:39] 6< 220 mail.physics.ox.ac.uk Microsoft ESMTP MAIL Service 
ready at Sun, 19 Sep 2010 22:15:25 +0100
[2010-09-19 23:14:39] 6> EHLO astro.ox.ac.uk^M
[2010-09-19 23:14:39] 6< 250-mail.physics.ox.ac.uk Hello [77.4.235.134]
[2010-09-19 23:14:39] 6< 250-SIZE 20971520
[2010-09-19 23:14:39] 6< 250-PIPELINING
[2010-09-19 23:14:39] 6< 250-DSN
[2010-09-19 23:14:39] 6< 250-ENHANCEDSTATUSCODES
[2010-09-19 23:14:39] 6< 250-STARTTLS
[2010-09-19 23:14:39] 6< 250-AUTH NTLM
[2010-09-19 23:14:39] 6< 250-8BITMIME
[2010-09-19 23:14:39] 6< 250-BINARYMIME
[2010-09-19 23:14:39] 6< 250 CHUNKING
[2010-09-19 23:14:39] 6> STARTTLS^M
[2010-09-19 23:14:39] 6< 220 2.0.0 SMTP server ready
[2010-09-19 23:14:39] ssl_check_preauth: hostname check passed
[2010-09-19 23:14:39] X509_verify_cert: unable to get local issuer certificate 
(20)
[2010-09-19 23:14:39]  
[/CN=winfe.physics.ox.ac.uk/CN=thphys.ox.ac.uk/CN=teaching.physics.ox.ac.uk/CN=smtps.physics.ox.ac.uk/CN=physics.ox.ac.uk/CN=imaps.physics.ox.ac.uk/CN=exchange.physics.ox.ac.uk/CN=exchange-cas3.physics.ox.ac.uk/CN=exchange-cas2.physics.ox.ac.uk/CN=exchange-cas1.physics.ox.ac.uk/CN=autodiscover.thphys.ox.ac.uk/CN=autodiscover.physics.ox.ac.uk/CN=autodiscover.atm.ox.ac.uk/CN=autodiscover.astro.ox.ac.uk/CN=atm.ox.ac.uk/CN=astro.ox.ac.uk/C=GB/ST=Oxfordshire/L=Oxford/O=University
 of Oxford/OU=Physics/CN=mail.physics.ox.ac.uk]
[2010-09-19 23:14:39] X509_verify_cert: unable to get local issuer certificate 
(20)
[2010-09-19 23:14:39]  [/C=US/ST=UT/L=Salt Lake City/O=The USERTRUST 
Network/OU=http://www.usertrust.com/CN=UTN-USERFirst-Hardware]
[2010-09-19 23:14:39] ssl_check_preauth: digest check passed
[2010-09-19 23:14:39] trusted: /C=US/ST=UT/L=Salt Lake City/O=The USERTRUST 
Network/OU=http://www.usertrust.com/CN=UTN-USERFirst-Hardware
[2010-09-19 23:14:39] ssl_check_preauth: hostname check passed
[2010-09-19 23:14:39] ssl_check_preauth: signer check passed
[2010-09-19 23:14:39] SSL connection using TLSv1/SSLv3 (AES128-SHA)
[2010-09-19 23:14:40] 6> EHLO astro.ox.ac.uk^M
[2010-09-19 23:14:40] 6< 250-mail.physics.ox.ac.uk Hello [77.4.235.134]
[2010-09-19 23:14:40] 6< 250-SIZE 20971520
[2010-09-19 23:14:40] 6< 250-PIPELINING
[2010-09-19 23:14:40] 6< 250-DSN
[2010-09-19 23:14:40] 6< 250-ENHANCEDSTATUSCODES
[2010-09-19 23:14:40] 6< 250-AUTH NTLM LOGIN
[2010-09-19 23:14:40] 6< 250-8BITMIME
[2010-09-19 23:14:40] 6< 250-BINARYMIME
[2010-09-19 23:14:40] 6< 250 CHUNKING
[2010-09-19 23:14:40] SASL local ip: 192.168.1.36;64383, remote 
ip:163.1.74.81;587
[2010-09-19 23:14:40] External SSF: 128
[2010-09-19 23:14:40] External authentication name: [email protected]
[2010-09-19 23:14:40] Authenticating (NTLM)...
[2010-09-19 23:14:40] 6> AUTH NTLM [snip hash]
[2010-09-19 23:14:40] 6< 334 [snip long hash]
[2010-09-19 23:14:40] mutt_sasl_cb_authname: getting authname for 
mail.physics.ox.ac.uk:587
[2010-09-19 23:14:40] mutt_sasl_cb_pass: getting password for 
[email protected]@mail.physics.ox.ac.uk:587
[2010-09-19 23:14:43] 6> [snip long hash]
[2010-09-19 23:14:48] 6< 535 5.7.3 Authentication unsuccessful
[2010-09-19 23:14:48] SASL authentication failed

> By the way, if I had to guess I'd say that the problem is that the
> server is advertising NTLM authentication but really only wants a
> plain password. You can fix this by setting
> smtp_authenticators="plain" in your muttrc, instead of letting SASL
> pick the strongest it can find.

With smtp_authenticators="plain", authorization fails and .muttdebug0 ends with:

2010-09-19 23:10:21] smtp_authenticate: Trying method plain
[...]
[2010-09-19 23:10:25] Authenticating (PLAIN)...
[2010-09-19 23:10:25] 6> AUTH PLAIN  [snip hash]
[2010-09-19 23:10:30] 6< 504 5.7.4 Unrecognized authentication type
[2010-09-19 23:10:30] SASL authentication failed

so I assume that plain is not right. (This ties in with the NLTM method Apple 
Mail autoselects and successfully uses for this server following a test 
connection.)

Any ideas?

-- Mike

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