Re: Having some problems with a FreeBSD mail server (SMTP)

2008-07-31 Thread Patrick Lamaizière
Le Wed, 30 Jul 2008 18:35:17 -0600,
Andrew Falanga [EMAIL PROTECTED] a écrit :

 Hi,
 
 I run a mail server for my church.  Today I was called that folks are
 able to receive, but not send their mail.  They are all currently
 configured for POP3 (I use dovecot).
 
 At home I tried to send mail to two different e-mail accounts of mine
 using the church e-mail server and was successful.  I used KMail for
 this.
 
 As I look through /var/log/maillog I do not even see
 authid=their_user_ids in the mail log (I'm using TLS with
 sendmail).  One of the pastor's told me the error he's seeing is
 timeout.  They are using Outlook, I'm not sure of the version.
 What problems do people here usually encounter with Outlook mail
 clients and their SMTP servers?
 
 At this point, I'd just like to have some leads.  Any ideas what
 might be keeping them from sending?  They can all log in and receive
 e-mail POP3.

May be their ISPs filter the port 25 now?
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Re: Having some problems with a FreeBSD mail server (SMTP)

2008-07-31 Thread Jonathan McKeown
On Thursday 31 July 2008 02:35, Andrew Falanga wrote:
 Hi,

 I run a mail server for my church.  Today I was called that folks are able
 to receive, but not send their mail.  They are all currently configured for
 POP3 (I use dovecot).

 At home I tried to send mail to two different e-mail accounts of mine using
 the church e-mail server and was successful.  I used KMail for this.

 As I look through /var/log/maillog I do not even see
 authid=their_user_ids in the mail log (I'm using TLS with sendmail).  One
 of the pastor's told me the error he's seeing is timeout.  They are using
 Outlook, I'm not sure of the version.  What problems do people here usually
 encounter with Outlook mail clients and their SMTP servers?

 At this point, I'd just like to have some leads.  Any ideas what might be
 keeping them from sending?  They can all log in and receive e-mail POP3.

I'm using TLS and SMTP AUTH with sendmail - all my users are on Microsoft 
Outlook 2003 (bar one on Thunderbird and me on KMail).

Outlook didn't do TLS properly until Outlook 2003 Service Pack 2 or 3 - the 
symptom was repeated timeouts on trying to send mail. Even after upgrading 
all the users to SP3, we still occasionally have a similar problem. A user 
will try to send mail, the TLS negotiation will time out, and from that point 
on mail will just accumulate in the outbox. Outlook has to be closed down and 
restarted before it will correctly try the TLS connection again.

We also encountered another issue, which may or may not be related to using a 
Windows AD domain, which was that Outlook will reuse message-IDs - generally 
by copying the message-ID of an original message and using it as the 
message-ID for the reply. This one bit me twice: once when a user (quite 
correctly) complained that she was losing email. On investigation, it turned 
out that her manager had sent three or four different messages in reply to 
messages of hers, and Cyrus imapd had binned them all as duplicates based on 
the copied message-ID. I had to switch off duplicate suppression in imapd.

The second time - which I haven't found a solution for - is in Mailman. The 
HTML pages for archives are built using the assumption that message-IDs are 
unique: the result is that when two messages have the same message-ID, only 
one of them will appear in the archive. (Which one is random, so I suspect 
Mailman is using the message ID as a hash key internally).

I get the feeling that Microsoft pay lip-service to the standards, but don't 
really carry out proper testing against anything other than Microsoft 
Exchange (after all, why would you use anything else?!). Outlook doesn't 
support IMAP well.

Worst, from my point of view, I have regular complaints that people using POP3 
are losing email. By using telemetry in Cyrus imapd, I've been able to 
establish that there's no problem server-side: Outlook is downloading the 
mail, and then throwing it away. Try telling a user that Microsoft stuffed 
up, though.

(Sorry - this turned into an Outlook rant. I hope you find some benefit in the 
early paragraphs, before I started frothing at the mouth and throwing my 
toys).

Jonathan
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Re: Having some problems with a FreeBSD mail server (SMTP)

2008-07-31 Thread Andrew D

Andrew Falanga wrote:

Hi,

I run a mail server for my church.  Today I was called that folks are able to 
receive, but not send their mail.  They are all currently configured for POP3 
(I use dovecot).


At home I tried to send mail to two different e-mail accounts of mine using 
the church e-mail server and was successful.  I used KMail for this.


As I look through /var/log/maillog I do not even see authid=their_user_ids 
in the mail log (I'm using TLS with sendmail).  One of the pastor's told me 
the error he's seeing is timeout.  They are using Outlook, I'm not sure of 
the version.  What problems do people here usually encounter with Outlook 
mail clients and their SMTP servers?




Have you even tried to get them to telnet to port 25, 465(for tls/ssl) 
to see what happens?


If their ISP is blocking port 25 then you can get them to send their 
mail using port 465 (with TLS/SSL) or using the SMTP submission port 
which is on port 587.


HTH
cya
Andrew

At this point, I'd just like to have some leads.  Any ideas what might be 
keeping them from sending?  They can all log in and receive e-mail POP3.


Thanks,
Andy
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RE: Having some problems with a FreeBSD mail server (SMTP)

2008-07-31 Thread Barry Byrne
 

 -Original Message-
 From: [EMAIL PROTECTED] 
 [mailto:[EMAIL PROTECTED] On Behalf Of 
 Andrew Falanga

 I run a mail server for my church.  Today I was called that 
 folks are able to 
 receive, but not send their mail.  They are all currently 
 configured for POP3 
 (I use dovecot).
 
 At home I tried to send mail to two different e-mail accounts 
 of mine using 
 the church e-mail server and was successful.  I used KMail for this.
 
 As I look through /var/log/maillog I do not even see 
 authid=their_user_ids 
 in the mail log (I'm using TLS with sendmail).  One of the 
 pastor's told me 
 the error he's seeing is timeout.  They are using Outlook, 
 I'm not sure of 
 the version.  What problems do people here usually encounter 
 with Outlook 
 mail clients and their SMTP servers?
[EMAIL PROTECTED]

Andrew:

I've seen a similar problem from time to time with Outlook 2003 clients. For
seemingly no reason whatsoever, they give a timeout sending mail. Googling
the error code throws up many with the same error and no solution that I've
found. Telneting to port 25 or even running the Outlook test mail account
feature still work, while Outlook comlains it can't send. 

The workaround is to quit Outlook and start again. By quitting Outlook, the
user must choose 'exit' from the 'file' menu. Simply closing the close box
still leaves Outlook in memory and the problem remains. The problem seems to
happen perhaps once or twice a month for some users. 

Regards,

Barry

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Re: Having some problems with a FreeBSD mail server (SMTP)

2008-07-31 Thread Andrew Falanga
On Thursday 31 July 2008 03:31:36 Barry Byrne wrote:


 Andrew:

 I've seen a similar problem from time to time with Outlook 2003 clients.
 For seemingly no reason whatsoever, they give a timeout sending mail.
 Googling the error code throws up many with the same error and no solution
 that I've found. Telneting to port 25 or even running the Outlook test mail
 account feature still work, while Outlook comlains it can't send.

 The workaround is to quit Outlook and start again. By quitting Outlook, the
 user must choose 'exit' from the 'file' menu. Simply closing the close box
 still leaves Outlook in memory and the problem remains. The problem seems
 to happen perhaps once or twice a month for some users.

 Regards,

 Barry


To everyone who responded,

Thanks for the great suggestions.  A couple of you replied that they've seen 
issues with this and resolved them by closing down Outlook, by the File -- 
Exit method rather than the X in the upper right.  I'm really beginning to 
suspect this because the pastor I was working with told me that our senior 
pastor explained to him that he could send from a particular coffee shop in 
town when he couldn't from church.

Though I can't personally see a down side to having an office in a Starbucks 
(I don't know the name of the actual shop they were in), I think that the 
Outlook client get's some bad stuff in the cache that is flushed out when 
they shutdown their computers to go make the journey.  The pastor I was 
dealing with said he went there and all of this mail sent without a hitch.

The other possibility is that the ISP is blocking some particular port.  We 
did just change ISP's within the last 2 weeks and according to this pastor, 
these sending problems originated at that time.  We'll see.

Andy
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Re: Having some problems with a FreeBSD mail server (SMTP)

2008-07-30 Thread Derek Ragona

At 07:35 PM 7/30/2008, Andrew Falanga wrote:

Hi,

I run a mail server for my church.  Today I was called that folks are able to
receive, but not send their mail.  They are all currently configured for POP3
(I use dovecot).

At home I tried to send mail to two different e-mail accounts of mine using
the church e-mail server and was successful.  I used KMail for this.

As I look through /var/log/maillog I do not even see authid=their_user_ids
in the mail log (I'm using TLS with sendmail).  One of the pastor's told me
the error he's seeing is timeout.  They are using Outlook, I'm not sure of
the version.  What problems do people here usually encounter with Outlook
mail clients and their SMTP servers?

At this point, I'd just like to have some leads.  Any ideas what might be
keeping them from sending?  They can all log in and receive e-mail POP3.

Thanks,
Andy


Andy,

These errors can be some of the hardest to track down.  I would go to one 
of the problem users and try sending email with their client as you watch 
the maillog from a ssh window.


Outlook and Outlook express send mail a bit differently so you will need to 
know which client they are using.  Also, if sending mail was working, and 
just stopped, I'd suspect some microsoft patch as the culprit.


-Derek

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