Gmail, SMTP, spam and their web interface...
 

Sorry for the confusing title...

In recent weeks I've began to notice that quite a lot of my email never reached the recipient - I use Thunderbird to sent through the Gmail SMTP server on a domain I have setup with Google for domains.

Finally, someone I emailed, sent me a message letting me know that my email had ended in her spam folder - apparently many corporate email servers don't like the Gmail SMTP server, so they flag it as spam.

One quick (and effective) solution has been to send important messages through their web interface - those always seem to be delivered.

Just in case anyone here has wondered whether their email was being spam flagged...

Have you configured an SPF record for your domain covering the gmail servers? Also, have you seen the headers from the received message to determine if there is anything "special" in the X-Headers that could indicate why that happened?

The conspiracy theorist in me loves that Outlook can just decide that messages sent from gMail are spam and that MS can tweak that setting as they wish on a monthly basis as they roll out the junk email filter updates. I'm sure that nothing sent from the Hotmail/Live service is getting flagged.

I have Google Apps set up as well and have not really had a problem with it. However, if my memory serves me correctly from when I was setting my DNS records up for my domain, I did not change anything to really do with the SMTP server as you use all gmail servers. In fact I think I left my old SMTP server as is to have it set up as a backup. This makes me question why it would really matter if you are sending an email from the Web interface vs Thunderbird.

I'm guessing there is something in the headers that reveals it all, but I haven't had the time to look into it. I just noticed that a lot of people never replied. Then when I resent my email from the web, they all responded within a day.

Yes - I have these two spf entries:

v=spf1 mx:aspmx.l.google.com ~all v=spf1 include:gmail.com include:google.com ~all

v=spf1 mx:aspmx.l.google.com ~all

Those should be sufficient?

I'm going to ask some people to dig into their spam folder to find why I was being blocked...

Another (remote) possibility:

Could someone mistakenly flag one of your email as spam that somehow triggered the flag then added you to the black/block master list?

I read somewhere (maybe on FT?) it took quite a while before this person could clear things up and be unblocked with ISPs.

ScottC...aren't you the computer expert? ;)

FWIW...I use gmail through the web interface and via SMTP and haven't noticed any issues at all.

I’ve tried flagging spam with my Yahoo accounts, but that never really stopped anything so I’m not sure how effective the “report spam” feature is.

Gmail may be a whole other ballgame though. I was able to get one of my Gmail accounts reactivated, so I’m considering moving more over to Google since they keep coming out with cool things like Google Voice (received my invite after ~3 weeks).

Send yourself a test message and see what server the email actually comes from.... the spf record might be wrong.

These SPF entries are incorrect.

The recommended SPF string for Google Apps-hosted domains can be found at http://www.Google.com/support/a/bin/...n&answer=33786

You shouldn't need the second "include:gmail.com".

The best place to check you spf recored is here: http://www.kitterman.com/spf/validate.html

I don't think you need the second "include:gmail.com".

The best place to check you spf recored is here: http://www.kitterman.com/spf/validate.html

I have a perhaps semi-related issue.

I use a pop3 email client (a program I've used for over 15 years) to retrieve and send email. I too use gmail's smtp server. At the time I set this up it was so much more reliable than my isp's smtp server. It's also handy to have gmail archiving all my sent mail.

In my email program, I have both the "From" and "Reply-to" fields filled in with my default email address where I want to get replies.

90% of the time, that's where replies come.

But the other 10% (and this seems to be increasing) get sent straight to my gmail account (where I then have to forward it on to my real email account).

Is this a matter of what program the responder is using? Why, in these cases, doesn't the header in my message (which I can confirm contain the correct Reply-To instruction) get obeyed?

GMail SMTP server adds a Sender: header, which Outlook [idiotically] displays as "From: <Sender: Header> on behalf of <From: Header>":

http://viewstream.com/blog/wp-conten...behalf-of1.JPG

Now that you mention it, I have indeed seen that "On behalf of" verbiage in replies.

(I've also noticed that when folks forward me a message sent from Outlook so I can have an email address, Outlook strips out the actual email address and just leaves the name. Really helpful. :rolleyes:)

Is Outlook's behavior in this regard RFC-allowed?

Outlook is displaying it correctly based on the information in the headers. Gmail's decision to add the extra header information is the cause of the problem.