Ignoring the irony, you could signup with Microsoft's spam filtering service (formerly frontbridge) or postini (now google) and use them as outbound relays. They will do outbound relay, with attendant spam filtering and increases in deliverability. That means a lot more people will accept your mail when it is being relayed by postini/front bridge. I believe postini will do this for any account, even one that has only, say, one e-mail address being filtered by them and the rest silently passed. Heck, you may not even need to point your mx records to their servers- they just need a reinjection method for outbound filtering if I recall correctly. Again, I acknowledge the irony involved in such a solution. --D On Tue, Sep 28, 2010 at 9:05 PM, Erik L <erik_list@caneris.com> wrote:

Google appears to have blacklisted our domain. From the edge MTA, I sent three messages, differing only in the From header: 1. valid email @klssys.com 2. valid email @caneris.com 3. abc123@caneris.com

1 not spam; 2 & 3 spam

Return-Path of all three was still another address @caneris.com and the two SPF passed headers were still there. The body & subject of all messages was simply "testing5". The recipient even clicked on "not spam" on #2 prior to #3 being sent.

At least it explains why all the other standard stuff we all looked at didn't explain the issue.

The next (and last) question is: does anyone have a clueful Google mail ops contact?

Thanks again for all the help and sorry for the OT noise.

Erik

----- Original Message ----- From: "Erik L" <erik_list@caneris.com> To: "William Pitcock" <nenolod@systeminplace.net> Cc: nanog@nanog.org Sent: Tuesday, September 28, 2010 7:17:45 PM Subject: Re: What must one do to avoid Gmail's retarded non-spam filtering?

Hi William,

I do so for our entire IP space on a regular basis. The edge MTA I mentioned in the reply to Bill shows up as "Neutral" there.

Thanks

Erik

----- Original Message ----- From: "William Pitcock" <nenolod@systeminplace.net> To: "Erik L" <erik_list@caneris.com> Cc: nanog@nanog.org Sent: Tuesday, September 28, 2010 6:06:49 PM Subject: Re: What must one do to avoid Gmail's retarded non-spam filtering?

Hi,

Have you checked the IronPort reputation scores for your mailserver IPs? Google uses this data as part of it's spam detection method.

William

On Tue, 2010-09-28 at 16:15 -0400, Erik L wrote:

...

I realize that this is somewhat OT, but I'm sure that others on the list encounter the same issues and that at least some folks might have useful comments.

An increasingly large number of our customers are using Gmail or Google Apps and almost all of our OSS/BSS mail is getting spam filtered by Google. Among others, these e-mails include invoices, order confirmations, payment notifications, customer portal logins, and tickets. Almost anything we send to customers on Google ends up in their spam folder. This results in a lot of calls and makes much of our automation pointless, never mind all the lost sales.

The problem is compounded by those who use mail clients and do not log in to the webmail at all, since they would never see the contents of the Google spam folder.

We have proper A+PTR records on the edge MTAs, proper SPF records for the originating domain, proper Return-Path and other headers, and so on. There isn't anything that I can think of other than the content itself which would be abnormal, and obviously the content is repetitive and can't be changed much. Is there something obvious which we've missed?

Aside from the following clearly impractical solutions, what can we do? 1. Asking everyone (including those we don't even know yet) to whitelist all of our addresses, to check their spam folders, and to click on "this is not spam" 2. Providing our own free e-mail service to everyone (including those we don't even know yet) and putting up "don't use Google" ads on all of our customer-facing systems

At least this isn't Hotmail where mail is just silently deleted with no NDR after it's accepted by their MTAs.

The call volume has been going up instead of down lately and it's gotten to the point where we're sending MTA log extracts to people to prove to them that we really did e-mail them.

Would greatly appreciate any advice.

Erik

-- -- Darren Bolding -- -- darren@bolding.org --