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I hope webmasters is the right place to ask this kind of question.

I have a website with about 60.000 people signed up. This site wasn't quite active in the last couple of years. That's why I decided to completely rebuild it. Now I'd like to send out a newsletter to all that people.

Well, my problem is that I have no idea how many of the mail addresses still are valid and furthermore the mail server wasn't sending any mails in the last three years so I'm asking myself what would happen if I'd send out such an amount of mails at once. I really don't want to screw up my reputation.

What's the best way to handle this?

My mail server is set up properly and I have all needed DNS records set but I don't think this helps in this particular case.

4 Answers 4

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If you need something very basic, then MailChimp or Constant Contact might be overkill. Amazon has the Simple Email Service (SES). It is very cheap and easy to implement. If a message bounces it is no big deal. They will automatically blacklist it from future mailings and send you a notification so you can remove it from the system.

There are two ways to send email with SES. If your server is already using SMTP to send email, it is as easy as pointing to the Amazon server. If you don't mind coding, you can also use the API to send messages.

https://aws.amazon.com/ses/

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  • Thanks, I didn't knew that service. This sound really amazing and cheap and I think it should be the best solution.
    – sleepless
    Commented Oct 30, 2015 at 9:49
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If you did make major upgrades to your site, check your database of email addresses, and only send email to those who gave consent to such mail. I hope that the first time these 60,000 people gave you their emails you did offer the option for them to opt out of promotional offers and all that stuff.

As for those who still opt in, I'd suggest creating a generic message telling people the new features they can expect to use and add a link in the email which they can use to unsubscribe from future emails.

You may want to add a small apology message in the email so that if someone else claimed ownership of some email addresses you have on file, they won't feel as inconvenienced.

Maybe start the email like this:

This message is for those who continue to use ______.com. If this is not you, we apologize and invite you to use the unsubscribe link below.

As for sending the actual email, it can be done in PHP or another programming language. Just loop through applicable emails and call the mail function for each one.

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    Thanks. The points are self evident for me. Of course I will give the possibility to opt out and so on. My main question however is the reputation thing. I want to prevent Gmail for example to flag me as a spam sender because I haven't send out emails for a long time and I don't know how many of the mails are still valid. Gmail could think that this are auto generated mail addresses and flag me as spammer than. That's my big concern.
    – sleepless
    Commented Oct 25, 2015 at 7:02
  • Well if you're sending one email per unique email address, then spam can't be an issue. But if you're sending hundreds of emails to one email address that the email account owner/manager doesn't want then it can count as spam. Commented Oct 25, 2015 at 7:03
  • Well, If that's true than everything would be fine. I was concerned because I heard that mail providers are flagging you as a spammer if you are sending too many mails to invalid addresses. Since I don't know if they are valid (I will know afterwards of course) I was quite concerned.
    – sleepless
    Commented Oct 25, 2015 at 7:08
  • then you could time the sending of emails. Maybe send like 100 a day or something? Commented Oct 25, 2015 at 7:09
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    @sleepless I think you should read this article about the warming up of the IP. sendgrid.com/docs/Classroom/Deliver/warming_up_ips.html
    – Aakash
    Commented Oct 29, 2015 at 22:24
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It would cost some money but sign up for a service like MailChimp or Constant Contact. This will provide two solutions for you, one it will notify you of any invalid emails and two it will automatically allow those who want to unsubscribe to do so immediately.

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  • Thanks. I'm already using MailChimp but only for a small amount of mails. Therefore I know that they also aren't that happy if you send too many mails to invalid addresses. It's quite expensive also because for this amount of mails I'd need to pay about $750.
    – sleepless
    Commented Oct 28, 2015 at 12:22
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I'd use amazon, like genepool99 said for your first batch which will filter out any blacklisted and non-existant emails, and it's via their smtp so won;t blacklist your domain (or shouldn't!)

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