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I have a website which I set up with Google Apps. Thus, I changed the DNS records (the MX records) to use Google's mail servers; in other words, when mail is received by my domain it is properly received by Google and ends up in the Google Apps mail app for my domain.

But almost every mail I send from my email which is received by a Gmail address (which is the vast majority of them), ends up in the spam box of the recipient. I am using my personal email account and taking advantage of the ability to send from multiple accounts, but I have set up the SMTP settings to use smtp.gmail.com with my custom domain email and not to just use my personal email as the forwarding email address. This, according to any Google Apps instructions I can find, is the correct SMTP server settings.

I am using this email as a support email for my Android apps; I can't afford for my replies to go in spam and my customers to assume that I didn't reply to them! This has happened several times now and each time I waited a day or two and then re-sent the mail from my personal email and got a response saying they never got the first email (from the Google Apps domain email address).

How in the world is Google flagging its own hosted email accounts as spam? They are simple plaintext messages, in fact they are always replies to messages sent explicitly to the email, so why in the world are they being marked as spam and what can I do about it??

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up vote 10 down vote accepted

If you are not already using SPF and DKIM to authenticate your email, these can help it get past some spam filters.

SPF identifies the servers that are authorized to send mail from your domain. If all mail sent from the domain is sent through Google Apps, see this page for instructions on creating an SPF record.

DKIM is used to add a digital signature to your message headers so that the recipient's mail system can verify its authenticity. See this page for instructions on enabling DKIM in Google Apps.

Neither of these guarantees that your messages will not be marked as spam, but they should help, assuming that your domain does not have a reputation for sending spam. (If users frequently report mail from your domain as spam then authenticating the message as being from your domain could actually hurt.)

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Thanks! Last night a while after asking my question (but before your answer) I actually found that exact page on SPF and added it to my DNS records. Indeed all mail is sent through Google Apps so hopefully it will help things. –  Ricket Mar 2 '11 at 15:04
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I know this is old but did this solve things for you? I have set up DKIM and SPF and all my mail is still marked as spam when I send it via a third party app (it seems to work fine when I reply via Gmail itself). So I was thinking maybe this change will take place in a couple of hours. –  Andy Ibanez Nov 10 '12 at 1:18
    
Leonnears, You will have to add the IP address of the server that the third party app is sending from. see link below. support.google.com/a/bin/answer.py?hl=en&answer=176600 –  user36788 Mar 20 '13 at 22:19
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