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I'm trying to send emails using EE > tools > communicate. I have tried PHP, SendMail, and now SMTP with no luck. The email send but goes into the spam folder.

Hotmail and Gmail are both sending to spam. I have created an email jim@mydomain.com and I'm sending from that domain. Normally I would tell Gmail that it is not spam, however this is for a client and they will change recipients often.

Ultimately I need my Freeform forms to NOT send to spam but for now I can't get this to work.

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It can be many reason for this - first needs to check if domain or Server IP (can be for shared hosting) was not blacklisted.

Then check email header - you will have a whole picture if any spam flags here, servers ip, from what server is come etc. For example your email can failed DomainKeys (DKIM) test.

What I usually do, is setup mail setting for using third-party services like SendGrid or Mandrill to prevent possible issues. Both this services have free packages which enough for most sites needs.

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Using SendGrid or Mandrill are great suggestions. Using Escort can help make that an easy process.

If you don't want to go that route you might also want to look into creating an SPF record wherever you are hosting your DNS for this domain name. That helps identify which mail servers are allowed to send email from a specific domain. There are a few wizards out there that can help you create SPF records such as http://www.spfwizard.net/ and then you need to work with your DNS host to add that record.

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