I've set up the 360Works email plugin with AWS and it's working properly. 

The 'email from' is an approved gmail account which is an address from our domain.

The 'reply to' address is the email address  for the contact from which we are sending the email so it is different from the 'email from' address.

Our user is selecting a number of her contacts to send an email to, then our script loops through the list and send an email to each recipient one at a time. We need the 'reply to' to be the user's email address. 

When the email is sent to a gmail address it generates a very scary warning for the recipient. Is there any way to avoid this problem?

As a followup to the previous post, when sent to a Yahoo address the email is dumped into the spam folder. 

Hi Kurt,

There is not really anything that can be done in the Email plugin that can make this not happen. Often times phishing emails will masquerade as coming from a legitimate source, like say from your bank, but the reply to address is on another domain so that the attacker can receive your information. Unfortunately, it seems Gmail has a blanket policy that any email that meets this criteria will see cause this warning. I'm curious, if you click "Looks Safe" do you still get the warning with subsequent emails with the same "email from" and reply to" addresses? Is it possible to change the reply-to email to be on the blackbirdconnect.com domain?

Hi Kurt,

A little bit of a follow up here, I found a few cases where someone is doing the same as you and getting the same issue. Namely this stack overflow post. They are using PHP but the principles remain the same. They allude to setting up SPF and DKIM records for your domain to help mitigate receiving mail servers marking emails as spam/phishing. This blog post outlines what those are. I am not sure if doing so will completely resolve this issue or if your domain already has them set up but it may be worth looking into.