I am in the process of setting up mass email service.
My question is: what are the best practices to achieve maximum deliver-ability.
More precisely - what should I do/know to prevent spam filters from blocking the emails (the emails are not spam).
for example- how can I tell if my IP address is blacklisted somewhere and how can I prevent it from becoming blacklisted. Is amazon web services a suitable platform due to dynamic IP addresses, what are the restrictions on the from address, can it be different from the mail server domain.... you get it....
Frankly the best way is not to do mass emails from anything remotely related to your domain. By definition anything unsolicited mass emailed is spam. If it's solicited then the recipients will whitelist it.
The short of it is: it's up to the recipient's site admin as far as what goes and what doesn't. Trying to make it so that it "100% goes through" is an exercise in futulity, because the admin at each site will have different policies on what is "valid". So if you want this to work, follow these simple rules:
Always sent to opt-in recipients, with an option to opt-out. Unsolicited means just that, and you'll just create animosity by not having recipients that asked for your email in the first place.
Don't get all drunk-happy with bizarre HTML formatting or all-images-mail, you'll just trigger filters. Good formatting is courteous and makes your offers look professional. Bad formatting often triggers a 'spam' tag.
Make sure your server follows SMTP guidelines, or you'll just get rejected (many spammers don't play by the rules and often send "broken" SMTP sequences, etc. in an effort to carpet-bomb as many messages as possible in the least amount of time)
Be reasonable about delivery rates, attempting to machinegun 1,000 mailings though a single connection is a sure-fire way to piss off the site's admin (or at least kick the rate limiter into the ON position), but sending one recipient at a time with 3 parallel deliveries might be acceptable.
Accept the fact that some sites simply don't want to talk to you, no matter how much you want to talk to them. This goes hand-in-hand with the following corollary:
The email server is owned by the site you're sending to, so they have every right to make a decision about how to treat the delivery of your message; this includes putting the message in quarantine, or even piping it to
/dev/null
I know it's late, but you are probably best off to use a Commercial Service for this type of E-Mail. They have a wealth of experience, and are usually way better in making sure e-mails get delivered than you can ever be.
I can't help you with all your question but this is where I check our IPs to see if they are blacklisted or not; MXToolBox. I try to do this daily but at least twice a week.
We've also setup various Feedback Loops with some emails hosts (RoadRunner, AOL, etc). Check out this whitepaper on it: http://www.datranmedia.com/downloads/whitepaper_feedbackloops.pdf. This makes you more legit and professional.
Hope this helps you!
Use software like PHPList to ensure that you do not send emails to people who do not want it.
Take this Email Server Test and implement its suggestions so that your emails do not appear like SPAM.