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Can't send mail using Mail.app, but can with Thunderbird

Hello,

I am having one heck of a time, and it's killing me. I am new to the
world of OS X but am adapting well, with one exception - Mail. Here's
the deal.

Using Thunderbird, I can send mail out with password authentication.
I can send it via port 25 normally or via port 465 via SSL.

I can also telnet to port 25 and see the standard email connection, and
I can even fake it out using the proper sequence of commands.
I can telnet to port 465, although since that's SSL I can't easily fake
key negotiation or anything like that - but, it does establish a
connection.

However, Mail just can't do it, using password authentication.
I've set mail to use port 25 without SSL.
I've set it to use port 465 with SSL.
Neither option works.

I am fortunate in that if I've recently checked my mail via IMAP, it
authenticates me for sending out for a few minutes, so if I set Mail to
just not use any password authentication, it works with or without SSL.
Even with this auto-auth though, if I have password authentication on,
it simply won't let me send mail.

I know that the SMTP server works - and I can send mail, although I
have to have my timing set really low on checking mail in order to
ensure that any send works right off the bat. I have my workaround, but
it's rather annoying. Any reason why it wouldn't authenticate with a
standard password?

System information:
iBook G4 1.33GHz w/ 512MB RAM
Mac OS X 10.4.2
Mail 2.0.3
SMTP Server: mail.pixelreflections.com - standard port 25, SSL port 465

Thanks in advance for any advice/thoughts that you all can offer. I
hope I'm posting in the right newsgroup for this sort of issue. If I'm
not, I apologize in advance, and would greatly appreciate a redirect.

0
brianarn (3)
10/24/2005 4:42:39 AM
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<brianarn@gmail.com> wrote:

[Snipped Text]

> System information:
> iBook G4 1.33GHz w/ 512MB RAM
> Mac OS X 10.4.2
> Mail 2.0.3
> SMTP Server: mail.pixelreflections.com - standard port 25, SSL port 465
> 
> Thanks in advance for any advice/thoughts that you all can offer. I
> hope I'm posting in the right newsgroup for this sort of issue. If I'm
> not, I apologize in advance, and would greatly appreciate a redirect.

Is this for the Gmail account I note you have (in the header)?

If so, you need SSL for outgoing on port 587, and SSL for incoming on
port 995. Set Authentication to 'Password'. In Thunderbird this should
be TLS.

It is unusual to have SSL set for mail through your own ISP's system,
have you tried leaving it to default settings?

-- 
Andy Hewitt **  FAF#1, (Ex-OSOS#5) - FJ1200 ABS
Honda Civic: Windows free zone (Mac G5 Dual Processor)
http://mysite.wanadoo-members.co.uk/thehewitts2/index.htm
(updated Aug 28 2005)
0
hairy.biker2 (116)
10/24/2005 8:48:25 AM
I managed to miss this reply. Whoops.

It's not for the gmail account I have, no. It's for a server that I
personally administer.

As mentioned in the snipped text, I've tried it in multiple
configurations.

* I've used the default settings, pointing at port 25 of this server,
using both server name and IP address.
* I've turned on SSL, switched the port over to 465, using both server
name and IP address.

I even tried again today, after updating to 10.4.3.

No matter how I've got Mail configured (SSL or no), if I'm trying to
use password-based authentication for my SMTP server, it doesn't work,
and keeps re-prompting me for a password.

It's not been a big deal really, because if I set auth to 'None' and
just check my mail before sending, I have no problems (yay for
auto-authentication on checking). It's just a really weird annoyance to
be unable to authenticate to my server.

Just for kicks, I decided to set up SMTP auth using the gmail
information you provided, and I was able to send out mail just fine.
This is very weird. I'm going to go do some digging and see what I can
pinpoint. It's very weird that it'll work in other programs, just not
in Mail.

0
brianarn (3)
11/3/2005 5:33:22 PM
I wanted to reply and say that I found what the problem is, although it
made little sense.

Based on information found here:
http://www.directadmin.com/forum/showthread.php?s=c5051ff69e8c2be3f2c941f0271352fd&threadid=2037&highlight=mac+Mail+smtp

It seems that my SMTP server (exim) was set up to use either PLAIN or
LOGIN authentication. This caused Mail.app to be unable to
authenticate. I'm not sure why. However, being that I can administer
the box, I was able to easily turn off the PLAIN portion, and so now
LOGIN is the only means of authentication, and Mail.app works like a
charm, no more problems.

Overall, a weird weird problem that I'm glad I found a fix of sorts
for, but really wish that I understood better. I can't even really tell
what value there is to AUTH PLAIN over AUTH LOGIN, but whatever - it
works now, and didn't break any other mail clients (as I can still send
with Tbird and webmail, and others report to me that Outlook still
works just fine).

0
brianarn (3)
11/3/2005 5:56:45 PM
Brian,

I believe that AUTH LOGIN sends the login and password base64 encoded 
and AUTH PLAIN sends the login and password in clear text.  The Apple
mail app supports the following authentication mechanisms, you can see 
this in the advanced tab of the mail.app account settings:

	Password, MD5-Challenge-Response, Kerberos Version 4, NTLM,
	and Kerberos version 5 GSSAPI.

Password must be the base64 encoded authentication if it is now working 
on your machine.

Many older email clients only support PLAIN such as older copies of 
outlook and I believe many browser email programs such as netscape only 
support PLAIN.  So, by eliminating PLAIN, you may be excluding cutomers 
with older clients or clients that support nothing but PLAIN.  PLAIN is 
safe as long as it is over SSL.

I see from your post to the link below that your mail server is a 
FreeBSD 4.8 machine?  I have a mail server running FreeBSD 5.4 with smtp 
auth and I have it configured to support the following mechanisms:
	
	AUTH LOGIN PLAIN GSSAPI DIGEST-MD5 CRAM-MD5

This allows a wide variety of email clients to use smtp auth on this 
machine.  On this machine smtp auth is also required, they may not send 
email through it unless they can authenticate using one of the above 
mechanisms.  I also encourage through arm twisting the use of SSL no 
matter what when PLAIN or LONG is used.  To see what mechanisms an smtp 
server supports, you can use the "ehlo auth" command after telnetting to 
port 25 on your mail server, just type:  'ehlo auth' and hit return.  I 
see that your server only issues:

250-AUTH LOGIN

My mail server shows the following when I issue the "ehlo auth" command:

250-AUTH LOGIN PLAIN GSSAPI DIGEST-MD5 CRAM-MD5

best regards
John

brianarn@gmail.com wrote:
> I wanted to reply and say that I found what the problem is, although it
> made little sense.
> 
> Based on information found here:
> http://www.directadmin.com/forum/showthread.php?s=c5051ff69e8c2be3f2c941f0271352fd&threadid=2037&highlight=mac+Mail+smtp
> 
> It seems that my SMTP server (exim) was set up to use either PLAIN or
> LOGIN authentication. This caused Mail.app to be unable to
> authenticate. I'm not sure why. However, being that I can administer
> the box, I was able to easily turn off the PLAIN portion, and so now
> LOGIN is the only means of authentication, and Mail.app works like a
> charm, no more problems.
> 
> Overall, a weird weird problem that I'm glad I found a fix of sorts
> for, but really wish that I understood better. I can't even really tell
> what value there is to AUTH PLAIN over AUTH LOGIN, but whatever - it
> works now, and didn't break any other mail clients (as I can still send
> with Tbird and webmail, and others report to me that Outlook still
> works just fine).
0
11/8/2005 2:22:03 AM
Brian,

Forgot to mention it but on a FreeBSD machine with smtp auth, only PLAIN 
works with the password database, the other mechansisms require an entry 
in the SASL password database see, /usr/local/sbin/saslpasswd2, for 
setting the users password in the SASL database.  So perhaps your 
problem with PLAIN and LOGIN had more to do with the password stored in 
your database(s), ie wrong password when using PLAIN (/etc/passwd) and 
correct password with using LOGIN with the SASL database.

John Rushford wrote:

> Brian,
> 
> I believe that AUTH LOGIN sends the login and password base64 encoded 
> and AUTH PLAIN sends the login and password in clear text.  The Apple
> mail app supports the following authentication mechanisms, you can see 
> this in the advanced tab of the mail.app account settings:
> 
>     Password, MD5-Challenge-Response, Kerberos Version 4, NTLM,
>     and Kerberos version 5 GSSAPI.
> 
> Password must be the base64 encoded authentication if it is now working 
> on your machine.
> 
> Many older email clients only support PLAIN such as older copies of 
> outlook and I believe many browser email programs such as netscape only 
> support PLAIN.  So, by eliminating PLAIN, you may be excluding cutomers 
> with older clients or clients that support nothing but PLAIN.  PLAIN is 
> safe as long as it is over SSL.
> 
> I see from your post to the link below that your mail server is a 
> FreeBSD 4.8 machine?  I have a mail server running FreeBSD 5.4 with smtp 
> auth and I have it configured to support the following mechanisms:
>     
>     AUTH LOGIN PLAIN GSSAPI DIGEST-MD5 CRAM-MD5
> 
> This allows a wide variety of email clients to use smtp auth on this 
> machine.  On this machine smtp auth is also required, they may not send 
> email through it unless they can authenticate using one of the above 
> mechanisms.  I also encourage through arm twisting the use of SSL no 
> matter what when PLAIN or LONG is used.  To see what mechanisms an smtp 
> server supports, you can use the "ehlo auth" command after telnetting to 
> port 25 on your mail server, just type:  'ehlo auth' and hit return.  I 
> see that your server only issues:
> 
> 250-AUTH LOGIN
> 
> My mail server shows the following when I issue the "ehlo auth" command:
> 
> 250-AUTH LOGIN PLAIN GSSAPI DIGEST-MD5 CRAM-MD5
> 
> best regards
> John
> 
> brianarn@gmail.com wrote:
> 
>> I wanted to reply and say that I found what the problem is, although it
>> made little sense.
>>
>> Based on information found here:
>> http://www.directadmin.com/forum/showthread.php?s=c5051ff69e8c2be3f2c941f0271352fd&threadid=2037&highlight=mac+Mail+smtp 
>>
>>
>> It seems that my SMTP server (exim) was set up to use either PLAIN or
>> LOGIN authentication. This caused Mail.app to be unable to
>> authenticate. I'm not sure why. However, being that I can administer
>> the box, I was able to easily turn off the PLAIN portion, and so now
>> LOGIN is the only means of authentication, and Mail.app works like a
>> charm, no more problems.
>>
>> Overall, a weird weird problem that I'm glad I found a fix of sorts
>> for, but really wish that I understood better. I can't even really tell
>> what value there is to AUTH PLAIN over AUTH LOGIN, but whatever - it
>> works now, and didn't break any other mail clients (as I can still send
>> with Tbird and webmail, and others report to me that Outlook still
>> works just fine).
0
11/8/2005 2:34:45 AM
Reply: