How to send emails for my website, and not be considered spam?

[Superstar]

Hi,

I have a question, I didn't want to make it public for certain reasons. <personal reason removed>

I have a bunch of email addresses, close to 50, and I want to send them out to market the site, however...how do I do it so I don't get flagged for sending spam? Also, how do I word them so they don't get sent to the users' spam folder?

I have a proxy server/program..the thing that changes your IP, and I can pick every country to change my IP to. Should I use that in this process?

Any help is greatly appreciated. Need to do this soon, so a reply asap is super appreciated I don't mean that rudely in anyway. I just want to get these sent out, so hopefully I can get some traffic before Christmas.

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[admin]

Make sure:
1. The DKIM is set up.
2. The SPF is set up.
3. The Sender ID is set up. (Note: This is NOT the same as SPF!)

... and there's more records a person can set, but for only ~50 subscribers, I'd really not worry about them. Keep it simple, just do the basics.

For help with mail records, refer to http://www.unlocktheinbox.com

Use the server that the site is on. Do NOT use a proxy.

Then use either
- plain text
- clean and basic HTML
- a simple newsletter template. Preferably NOT a free one, so spend $10 on ThemeForest to get a good one that is spam-free.
- a "simple" (learning curve!) mail service like MailChimp, which has ready-to-use basic templates

Our servers send thousands of emails per month, so we monitor them very closely.

That should point you in the right direction.

Tips:

1. Set the DNS entries up at least 3-4 days before sending a mass mail!
2. Send yourself LOTS of tests, to make sure it's working.
3. Be sure to read message headers. You'll need to understand what going on there.