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Unfortunately, there is no perfect answer. Every "spam" system can have different things it looks for to determine what is spam. If there was a simple list of things to do, then every spammer would do those things so their email would not wind up in spam. You will want to do some research, but here a a few things to consider: 1. The server sending the email should be an "authorized" sender for the domain in the from address. In this case you are using Gmail to send an email on behalf of 'bidsoliciationapp.com'. There are ways to change the MX records (similar to DNS records) to authorize a server for a particular domain. But, I think that would require reaction from Google as well if you want to use your current configuration. You may need to use a Google from address or use a dedicated emailing service that can help with the right configuration. Of course, that would cost money. I only understand these things tertiarily, so some of my 'facts' may be slightly off. 2. The name of the domain could be problematic with words such as "bids", "solicitation" could raise a red flag. 3. Content: I would not start with a "Hello Bob, please click <here> . . . " It just seems like something I would see in a Spam email. I don't know if that is part of the problem or not. What you can do: Set up an account with a few different email providers and send some samples of your current emails to them to see if any are flagged as spam. If so, then change the content to something completely innocuous. Does that go through w/o being detected as Spam? If yes, then you know it is the content causing the detection. If not, then it is likely something to do with the configuration/meta data.