Google Apps and on premise email

Here is the scenario:
Client has a hosted Lotus Domino (makes no difference what email system it is at the back end) system that uses Google Apps as its email gateway (both ways)
Client has a number of 'team' groups setup with SMTP Addresses in Domino
When an external email account (say a customer) sends an email to one of these team groups, the members of the group receive the email.

Except, only the internal members are getting these emails. If, contained in one of these groups, is an external email address - say a consultant etc. the customer receives an NDR that states:
Delivery has failed to these recipients or groups:
user@recipient.com
A problem occurred while delivering this message to this email address. Try sending this message again. If the problem continues, please contact your helpdesk.
The following organization rejected your message: gmail-smtp-relay.l.google.COM.
Diagnostic information for administrators:
Generating server: webmail.clientdomain.com
user@recipient.com
gmail-smtp-relay.l.google.COM
Remote Server returned '<gmail-smtp-relay.l.google.COM #5.0.0 X-Notes; Error transferring to gmail-smtp-relay.l.goo gle.COM; SMTP Protocol Returned a Permanent Error 550 5.7.1 Invalid cr edentials for relay [client.server.ip.addr]. md8sm67683wjb.3 - gsmtp>'

Any one seen this before?

Thanks
Mark/
LVL 13
Mark GalvinManaging Director / Principal ConsultantAsked:
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Sjef BosmanGroupware ConsultantCommented:
Are  you sure that Domino isn't involved? Just to make that 100% sure, can you verify that the server's log database does not contain references to mails received and rejected around thetimes that they were sent?
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Mark GalvinManaging Director / Principal ConsultantAuthor Commented:
Our Domino consultant has checked. The Domino server is passing the email over the to the Google stack for processing.

What we  believing is taking place here is that the Google Stack believes that it is being used by the external sender as some kind of relay and thus blocking the email.

If an internal user then forwards the email that was received from user@recipient.com to the external consultant it is processed and received without issue.
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Sjef BosmanGroupware ConsultantCommented:
As suggested on this page: https://productforums.google.com/forum/#!msg/apps/U1ibc6cJQZI/ul3MRx1bLcwJ : contact Google's Support Department and let them fix the issue.

Does the Domino server do a login into Gmail? That setting can be found in Domino's Configuration Settings document for the server, under Router/SMTP, Basic, Use authentication when sending messages to the relay host.
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Mark GalvinManaging Director / Principal ConsultantAuthor Commented:
Hi Sjef

Thats a good suggestion and we will try it. The Domino server currently doesnt log onto the Google App when relaying email and the NDR does state 'Invalid cr edentials for relay'.

If we turn this on, can we use any Google App account that is an admin?
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Sjef BosmanGroupware ConsultantCommented:
Probably, not sure... But try, by all means. :-)
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Mark GalvinManaging Director / Principal ConsultantAuthor Commented:
trying today.
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Mark GalvinManaging Director / Principal ConsultantAuthor Commented:
Tried to use my Google Apps account (which is full admin) and then tested:
Delivery has failed to these recipients or groups:
user@recipient.com
A problem occurred while delivering this message to this email address. Try sending this message again. If the problem continues, please contact your helpdesk.
The following organization rejected your message: gmail-smtp-relay.l.google.COM.
Diagnostic information for administrators:
Generating server: webmail.clientdomain.com
user@recipient.com
gmail-smtp-relay.l.google.COM
Remote Server returned '<gmail-smtp-relay.l.google.COM #5.0.0 X-Notes; Error transferring to gmail-smtp-relay.l.goo gle.COM; SMTP Protocol Returned a Permanent Error>'

Just to recap here:
webmail.clientdomain.com = my clients mail server
user@recipient.com = the external consultants email address that is a member of an distribution group on the clients internal mail system

The error here is not as specific as the original error, where it stated the credentials were wrong. Now it doesn’t really give a 'real' error.
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Sjef BosmanGroupware ConsultantCommented:
Where are the groups defined, in Google or in Domino?
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Mark GalvinManaging Director / Principal ConsultantAuthor Commented:
The groups and their members are configured on the Domino server. All the distribution occurs there.

The SMTP address of the group is configured on the Google App side as all that occurs there is the mail filtering and then routing through to Domini.

Thanks
Mark
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Sjef BosmanGroupware ConsultantCommented:
I hope you use the correct port to send mails to Google, see http://email.about.com/od/accessinggmail/f/Gmail_SMTP_Settings.htm

For outbound SMTP to a different provider, we use port 587 with Negotiated SSL, where the credentials are in the Configuration document.
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