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Google Mail is flagging my Outbound Mail in Google Apps!

Posted by geeknews at 10:30 AM on July 23, 2008

I am beyond irritated with Google at this moment. I have all of my domains email utilizing Google Apps Service which includes Gmail functionality for any persons .com address.

I have always used a desktop client like outlook or thunderbird. I run the service in IMAP and have a home machine and a travel machine that I primarily connect to Google to get the email.

The problem I am having is that many times when I am traveling Google starts flagging my mail as spam and people are not getting it. This is even happening in inter domain email aka from @rawvoice.com to @rawvoice.com

The only thing we can think of is that when I am in a Hotel or on my Sprint EVDO account that Google has some of those IP’s blacklisted. Thus when I send the email via thunderbird from one of those services the IP I am sending on gets embeded in the header. This is causing me a lot of concern because email is critical in our day to day operation and now it seems Google is blocking legitimate email and they are becoming a liability.

If I log into the web interface which i hate this problem does not seem to happen. Google you better get your act together on Google Apps or I will cancel the service and move to someone that can move email properly.

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3 Comments

  1. From Matt at 10:48 am on July 23, 2008

    I’m confused… is the email getting blocked on the way out, or is it being received and marked as spam?

    http://mail.google.com/support/bin/answer.py?answer=10514&topic=12852 might have some things worth looking at.

  2. From Todd Cochrane at 1:55 pm on July 23, 2008

    It gets received then marked as spam on the destination account.

  3. From Matt at 7:05 pm on July 23, 2008

    Ah, ok… double check that you’re using google’s SMTP server (instructions here: http://mail.google.com/support/bin/answer.py?hl=en&answer=13287). You can send mail for your gmail account using other SMTP servers, but it’ll look spammy. Might also be worth looking at the headers discussed in the help document in my previous comment.