Error "not permitted to 550-relay through this server" when sending email within our domain

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Glenn

unread,
Nov 6, 2007, 1:08:15 PM11/6/07
to Postini Support for Google Apps
We enabled Postini for our Google Apps email domain about a month
ago. Starting yesterday, our users are occasionally (but not always)
getting a bounceback email failure when sending emails to other users
within our domain, as follows:

---
Delivery to the following recipient failed permanently:

som...@ourcompany.com

Technical details of permanent failure:
PERM_FAILURE: SMTP Error (state 13): 550-exprod7og103.obsmtp.com
[64.18.2.159]:42828 is currently not permitted to 550-relay through
this server. Perhaps you have not logged into the pop/imap 550-server
in the last 30 minutes or do not have SMTP Authentication turned on
550 in your email client.
---

My guess is that this is related to the fact that we relay outbound
email via Postini - in our Google Apps email configuration, we have
set the "Email Gateway" to "outbounds7.ga.obsmtp.com", per the Postini
setup instructions.

This doesn't seem related to the actual email clients used by our
users (e.g. Outlook, Thunderbird, etc), although I'm not 100% sure.
It's possible the error has only occurred so far for POP3 users,
although it may have also occurred for people using the web Gmail
interface too. We're still trying to narrow this down (it's hard,
since the error only occurs occasionally).

Any advice? Any more info on what this error is all about? I
couldn't find much on it from a regular Google search, so I'm not even
sure I fully understand what the error is.

jasonhavens

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Nov 23, 2007, 12:07:38 PM11/23/07
to Postini Support for Google Apps
Glenn,

I'm certainly no expert, but I think that this issue is related to the
recipient's mail server settings. If those settings are relatively
high for security purposes, then your messages might be rejected
because that recipient's server can see that the IP address where your
message actually originated is different from Google's and/or
Postini's IP address through which you're routing your message.

The only solution that I can suggest is to log into the Google Apps
Internet-based interface and send the message from there. That way,
your message is technically "originating" from Google's IP address and
not being relayed from your actual IP address where your computer is
located. You might need to BCC yourself if you want to save a copy in
Outlook because domain-based Gmail will only save a copy online if
your settings dictate that.

It seems that other folks' servers would allow relaying through
Postini because so many organizations use Postini's servers in
conjunction with their own corporate/internal servers. I suspect that
most sophisticated IT departments allow a filter for messages routed
through Postini. Perhaps most other servers will eventually do so.

I hope that this helps. Hopefully others who are much more
technologically proficient will respond as well.

Kind regards,

Jason Havens

On Nov 6, 12:08 pm, Glenn <gl...@appirio.com> wrote:
> We enabled Postini for our Google Apps email domain about a month
> ago. Starting yesterday, our users are occasionally (but not always)
> getting a bounceback email failure when sending emails to other users
> within our domain, as follows:
>
> ---
> Delivery to the following recipient failed permanently:
>
> some...@ourcompany.com
>
> Technical details of permanent failure:
> PERM_FAILURE: SMTP Error (state 13): 550-exprod7og103.obsmtp.com
> [64.18.2.159]:42828 is currently not permitted to 550-relay through
> this server. Perhaps you have not logged into thepop/imap 550-server

Glenn

unread,
Nov 23, 2007, 4:53:23 PM11/23/07
to Postini Support for Google Apps
Jason,

Thanks for the ideas. Note that the error reported here happens when
people at our company send emails to their colleagues - we are all in
the same email domain. We didn't do anythign paritcularly special
with our domain security-wise, it is a typical Google Apps email
domain.

After working with Postini tech support on the above issue, they just
closed the case 2 days ago, with this comment: "This was an issue
with Google blocking sending IP's from Postini, Google has now
whiltelisted all our sending IP's and this no longer should be an
issue."

So this appears to be an issue between Google Apps and Postini - not
something directly under our control. I should say that, although the
errors seem to have gone away, we just had an occurrence of a new but
possibly related error when 1 user tried sending an email with
attachments to another user in our domain: "PERM_FAILURE: SMTP Error
(state 16): 552 5.7.0 Illegal Attachment 14si3241166wrl", and later in
the error message, "Received-SPF: softfail (google.com: domain of
transitioning X...@XXX.com does not designate X.X.X.X as permitted
sender) client-ip=X.X.X.X;" (where I've blanked out personal info with
X's).

I've opened a new Postini tech support case.

Glenn
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