Outlook ignores 5xx SMTP error codes - how to correct it?

[Tomasz Chmielewski]

I have this issue with Outlook 2003 from time to time - it seems to me
that Outlooks ignores the meaning of 5xx SMTP reply codes (permanent
failure), and tries to resend the message again. Although according to
RFCs, it shouldn't.


Here's what happens:

1. Clients attaches a 100 MB file and tries to send it in Outlook

2. SMTP server limit is 20 MB - so upon receiving, SMTP server replies
with a 552 error, and rejects the message.

3. Few minutes later, Outlook sends 100 MB again, it is rejected by the
SMTP server, Outlook sends it again, again, and so on.

What makes things worse, Outlook doesn't give any clear message that
sending the message has failed (at least, not clear to a non-technical
user).


Because of the above, bandwidth costs can go up in no time - just a few
users in a company which want to send a message bigger than allowed, and
Outlook will try to resend the message again and again, hour after hour,
day after day, until someone notices it.


Is there a fix for that in Outlook (or, perhaps - "enable
RFC-compliance" setting)?

 

[Roady [MVP]]

Is there anything between Outlook and the mail server? Virus scanners
integrating with Outlook are a known cause of resulting messages getting
stuck or downloaded over and over again because they do not correctly pass
through the server information received to Outlook which results in Outlook
trying to repeat the action.

 

[Tomasz Chmielewski]

Is there anything between Outlook and the mail server? Virus scanners
integrating with Outlook are a known cause of resulting messages getting
stuck or downloaded over and over again because they do not correctly
pass through the server information received to Outlook which results in
Outlook trying to repeat the action.

No, there is no virus scanner or anything like that integrated with Outlook.

 

[Tomasz Chmielewski]

No, there is no virus scanner or anything like that integrated with
Outlook.

And what's weird, if I try to send a message that is too large for a
mail server from another MUA (i.e., Thunderbird) it is rejected by the
SMTP server *immediately* - with a message that the server's maximum
allowed message size is XYZ.

Outlook has to send the whole message to reach the same conclusion.

What is missing in Outlook, then, that it can't detect server's
capability so early (or it doesn't report message's size to the server
as soon as it connects)?