C
Confused Mail Admin
I've run into an odd problem. I have Outlook 2002 SP2
configured with an Exchange account and an IMAP/SMTP
account on two different machines, both with the same
account information and settings for SMTP. Both machines
are on the same network. While there is a firewall, both
machines are treated identially by it.
On the first machine, Outlook can send email via the
IMAP/SMTP account and authenticates via SMTP AUTH
properly with the SMTP server. On the second machine,
Outlook fails to authenticate to the SMTP server and
returns a message stating "Recipient address rejected:
Relay access denied".
Logs on the SMTP server indicate that it did, in fact
reject the message, and that the SMTP connection was
initiated by the IP address assigned to the client (so it
is not a case of the message being passed to Exchange for
SMTP delivery).
A netowork packet capture at the SMTP server of the
conversation with the failing client shows that, despite
the server identifying itself as ESMTP capable, the
client responds with a HELO rather than an EHLO. Thus
never sees the ESMTP capabilities of the server and never
attempts to respond to AUTH. Since the client does not
authenticate to the server, relay access is denied.
The wierd thing is that the other client appears to
authenticate properly. Both clients are configured in
exactly the same way (at least from a user configurable
options stand point. I did not verify a match on all
related registry settings).
I'm stumped as to what to look for as the cause of this
behavior. Clearly the failing client should be issuing
the EHLO and then attempt to authenticate. Has anyone
run into a similar problem, and (with luck) perhaps a
solution? Any suggestions about what to look at next?
I've checked the Knowledge Base and have not found
anything that has been of any help.
configured with an Exchange account and an IMAP/SMTP
account on two different machines, both with the same
account information and settings for SMTP. Both machines
are on the same network. While there is a firewall, both
machines are treated identially by it.
On the first machine, Outlook can send email via the
IMAP/SMTP account and authenticates via SMTP AUTH
properly with the SMTP server. On the second machine,
Outlook fails to authenticate to the SMTP server and
returns a message stating "Recipient address rejected:
Relay access denied".
Logs on the SMTP server indicate that it did, in fact
reject the message, and that the SMTP connection was
initiated by the IP address assigned to the client (so it
is not a case of the message being passed to Exchange for
SMTP delivery).
A netowork packet capture at the SMTP server of the
conversation with the failing client shows that, despite
the server identifying itself as ESMTP capable, the
client responds with a HELO rather than an EHLO. Thus
never sees the ESMTP capabilities of the server and never
attempts to respond to AUTH. Since the client does not
authenticate to the server, relay access is denied.
The wierd thing is that the other client appears to
authenticate properly. Both clients are configured in
exactly the same way (at least from a user configurable
options stand point. I did not verify a match on all
related registry settings).
I'm stumped as to what to look for as the cause of this
behavior. Clearly the failing client should be issuing
the EHLO and then attempt to authenticate. Has anyone
run into a similar problem, and (with luck) perhaps a
solution? Any suggestions about what to look at next?
I've checked the Knowledge Base and have not found
anything that has been of any help.