On Thu, Mar 27, 2014 at 08:45:01AM +0100, martijn.list wrote: > Has anyone on this list has any experience in setting up an outbound > gateway for Google Apps and/or Exchange online?
I set up Google Apps some years back, but have switched jobs since and have forgotten some of the details. We definitely put in counter-measures that prevent other Google Apps customers from relaying via our outbound servers. Google should be able to tell you about available options for that. At the very least we had: * Google Apps outbound flow was to port 587 with STARTTLS via a dedicated set of Postfix machines. * The envelope sender domain was restricted to our Google Apps domain, and we used reject_unlisted_sender. * We were "big enough" to ask them to use client certificates to authenticate to the outbound server. We had a long-standing feature request to allow us to provision these by uploading a PKCS12 or similar key + cert bundle via the domain administrator interface, so that client certs would be per customer, not global for Google Apps. Without this feature they notified us before deploying new client certs (which was a nuisance for them and us). Don't know whether the requested client cert support got implemented. So $previous_employer may still be relying on Google's default client certs (which unlike the sender domain are not client specific). * We also asked Google to authenticate our server's TLS cert. * We also operated our own inbound MX hosts, and used Google Apps only as a mailstore, not an MX provider. Envelope rewriting rules kept the mail flows from looping (the internal mailbox address of a Google Apps user was a custom domain, which was rewritten back to the primary address in smtp_generic_maps during hand-off to Google's relay). That was all then, things may be different now, ideally better, with more options available, but things don't always improve. Sometimes the simplest options for the mass-market become the only options. -- Viktor.