Neither spam, nor snow...
October 28, 2008 6:53 AM   Subscribe

NotSpamFilter: Why are letters sent from my Gmail and Google Apps email addresses getting intermittently marked as spam in Outlook?

For six months or so, I've noticed at a great many of my letters have not reached their recipients. Personal correspondence. (No attachements, no forwards, no idiotic chain letters. I have NEVER sent a letter to more than two people at a time.) I chalked it up to problems with their ISPs, as letters sent from both Gmail AND my custom domain (hosted on Google Apps) were vanishing into the ether. (Once, a rejection letter -- reprinted below.)

I also considered that, perhaps, keywords in my messages were triggering problems. When writing about the novel "Oryx and Crake", for example, I can almost see how a filter might interpret that as gibberish and kill it.

In the past, Postini has blocked the occasional letter I've sent. (I tested by sending to my company address.)

Last night, I began an experiment. I sent a letter from my Google Apps account to my company email address,, and The letter made it to everyone EXCEPT my company.

Outlook's spam folder ate it. (I'm using the default settings.)

I resent the same letter through my standard @gmail address. Again, Outlook's spam folder nabbed it.

I resent the same letter through my address. It made it to my Outlook inbox.

I resent the same letter through my address. It made it to my Outlook inbox.

SO... my question! Why are my letters sent through Gmail and Google Apps being flagged as spam, but not the same letter through other providers?

I'm going to be querying literary agents this week, and as you can imagine, it's very important that my letters not be eaten by a zealous Microsoft product. Must I switch email accounts? (The, and addresses are not primary accounts for me, and I'd hate for my professional correspondence to have asinine "Check out for the best weather forecast!" footers.)

For what it's worth, I've checked the MX servers on my Google Apps (all good) and have run my domain through this blacklist check. Again, all good.

I can wrap my brain around a personal domain getting the evil eye from spam filters... but Gmail?

This is wearying and worrisome. Any insight will be appreciated.

(Upon reflection, if my writing style is reminiscent of junk email, it may not matter whether the agents get my queries or not.)

The only "email rejected" letter I've ever received, long ago, is below. I do not know if it is relevant.


This is an automatically generated Delivery Status Notification

Delivery to the following recipient failed permanently:

Technical details of permanent failure:
PERM_FAILURE: Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 571 571 Message Refused (state 18).
posted by rentalkarma to Computers & Internet (7 answers total)
I have experienced this as well with my gmail account and my hosted domain. Here is one explanation from the mothership itself.

As for what is going on here is that I think some organizations penalize incoming gmail sent messages in a way that makes it easier for their other analysis to ding a message as spam. Lots of anti-spam products work with a concept of a per-message "score" to determine what to do with a message. If you score drops below a threshold then the receiving organization marks the message as spam...if it is below a further threshold the message might bounce or it just might be deleted.
posted by mmascolino at 7:10 AM on October 28, 2008

Are you definitely sending the emails through Google, rather than via another SMTP server?
posted by malevolent at 7:24 AM on October 28, 2008

My MX records (domain hosted on Doteasy) are as follows:


After configuring that, I just log into Google Apps and send email through the normal Gmail web interface. No custom SMTPs, etc.

As for SMTP addresses for my standard Gmail account, I'm using whatever the default is.

In neither case am I using a desktop-based client to compose or send email. It is all done through the web.
posted by rentalkarma at 7:33 AM on October 28, 2008

UPDATE: The letter sent through MobileMe is also filtered by Outlook.

So far:
Google Apps - BAD
Gmail - BAD
MobileMe - BAD
Yahoo - GOOD - GOOD

Differential diagnoses for spam, people! (Pops Vicodin.)
posted by rentalkarma at 8:12 AM on October 28, 2008

Why are letters sent from my Gmail and Google Apps email addresses getting intermittently marked as spam in Outlook?

Because the Outlook spam filter blows chunks.
posted by flabdablet at 8:46 AM on October 28, 2008

Live and Outlook are both Microsoft, so I could see that the threshold might be set higher for email originating from

Also, Gmail's Captcha has been broken, allowing spammers to start harvesting gmail accounts for spam. Since Gmail was once safe ground, it's all the more appealing to spammers. Of course, you could still offer $50 for 2,000 valid gmail accounts, and find someone willing to do the work by hand ($50 USD is enough in some markets).
posted by filthy light thief at 10:15 AM on October 28, 2008

Two and a half cents per account is probably too much.
posted by flabdablet at 3:35 PM on October 28, 2008

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