ICal server and external invitations via 3rd party mail server

Hi everyone,
OS 10.6.5 Server:
Services running
AFP
DNS
iCal
Open Directory
Push Notification
We are currently testing iCal server and have configured it to send out invites via our mail server (which is running on a different server) by creating the com.apple.calendarserver user on our mail server.
Email notifications are then configured under the Enable Email Invitations tab in the iCal service of Server Admin as follows:
IMAP
Email address: [email protected]
Incoming server: mail.mytest.com
Port: 143 (not using SSL)
Username: com.apple.calendarserver
Password: secret
SMTP: mail.mytest.com
Port: 25 (not using SSL)
Server requires authentication
Username: com.apple.calendarserver
Password: secret
My test OD users are able to send out invites both internally to other iCal users and externally via email.
So for example, I invite someone to a meeting and enter their gmail address ([email protected]), the invitation goes out correctly - when I log into gmail I see the invitation.
When responding to the invitation (clicking Yes), the mail server receives the response from gmail and the iCal server collects the message via IMAP.
However, the iCal server doesn't seem to parse the received email correctly as I get the following error in the iCal error logs:
[twistedcaldav.extensions#info] Cannot authenticate proxy user 'com.apple.calendarserver' without X-Authorize-As header
2011-03-03 17:44:03+1100 [-] [mailgateway] 2011-03-03 17:44:03+1100 [AuthorizedHTTPGetter,client] [twistedcaldav.mail#error] Mail gateway failed to inject message <[email protected]> (Reason: 400 Bad Request)
2011-03-03 17:44:03+1100 [-] [mailgateway] 2011-03-03 17:44:03+1100 [AuthorizedHTTPGetter,client] [twistedcaldav.mail#debug] Failed calendar body: BEGIN:VCALENDAR
2011-03-03 17:44:03+1100 [-] [mailgateway] VERSION:2.0
2011-03-03 17:44:03+1100 [-] [mailgateway] CALSCALE:GREGORIAN
2011-03-03 17:44:03+1100 [-] [mailgateway] METHOD:REPLY
2011-03-03 17:44:03+1100 [-] [mailgateway] PRODID:-//Google Inc//Google Calendar 70.9054//EN
2011-03-03 17:44:03+1100 [-] [mailgateway] BEGIN:VEVENT
2011-03-03 17:44:03+1100 [-] [mailgateway] UID:43121576-1183-40C8-82D8-A052754AD1CE
2011-03-03 17:44:03+1100 [-] [mailgateway] DTSTART:20110406T080000Z
2011-03-03 17:44:03+1100 [-] [mailgateway] DTEND:20110406T090000Z
2011-03-03 17:44:03+1100 [-] [mailgateway] ATTENDEE;[email protected];CUTYPE=INDIVIDUAL;PARTSTAT=DECLINED;RO
2011-03-03 17:44:03+1100 [-] [mailgateway] LE=REQ-PARTICIPANT;X-NUM-GUESTS=0:mailto:[email protected]
2011-03-03 17:44:03+1100 [-] [mailgateway] CREATED:20110303T062518Z
2011-03-03 17:44:03+1100 [-] [mailgateway] DESCRIPTION:
2011-03-03 17:44:03+1100 [-] [mailgateway] DTSTAMP:20110303T064335Z
2011-03-03 17:44:03+1100 [-] [mailgateway] LAST-MODIFIED:20110303T064335Z
2011-03-03 17:44:03+1100 [-] [mailgateway] LOCATION:
2011-03-03 17:44:03+1100 [-] [mailgateway] ORGANIZER;CN=com.apple.calendarserver+07b1c044-9d98-4cdc-afe3-48139218ee35
2011-03-03 17:44:03+1100 [-] [mailgateway] @mytest.com:urn:uuid:B72794FB-3242-48D7-AC22-A584D279B9F9
2011-03-03 17:44:03+1100 [-] [mailgateway] SEQUENCE:3
2011-03-03 17:44:03+1100 [-] [mailgateway] STATUS:CONFIRMED
2011-03-03 17:44:03+1100 [-] [mailgateway] SUMMARY:one more test
2011-03-03 17:44:03+1100 [-] [mailgateway] TRANSP:OPAQUE
2011-03-03 17:44:03+1100 [-] [mailgateway] END:VEVENT
2011-03-03 17:44:03+1100 [-] [mailgateway] END:VCALENDAR
2011-03-03 17:44:03+1100 [-] [mailgateway]
I have set a rule on our mail server to bypass any spam filtering for all messages sent to the [email protected] address, but this doesn't seem to make any difference.
Does anyone else have this working ? Any ideas ?
Many thanks
Message was edited by: gen_bunty
null

The issue is not "user authorization". The issue is that the 3rd-party service does not accept all incoming relay requests unless there is authentication with a registered account (which we have). This protects the 3rd-party service from becoming the relaying host for the universe's spoofed and anonymous spam. My deduction is that there is no mechanism in UTL_MAIL to designate not only the 3rd-party ip-address:port (by-passing the local sendmail server) but also providing the username:password for the account there for authentication.
Plan A: I have attempted to follow directions for client-side SMTP Authentication for Relaying on the sendmail.org site.
I have not been successful in completing a simple mailx interactive test, much less completing a UTL_MAIL configuration.
I am scouring the user universe for someone who has put all the pieces together successfully and can advise. . . .
Edited by: StevenInTallyFl on Mar 26, 2010 3:50 PM
to clarify that I cannot get from UTL_MAIL to 3rd-party IP directly

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ICal server and external invitations via 3rd party mail server

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