Use your own mail server or outsource it?

Let's say you have a rather large mailing list of a few thousand email addresses and, well, sending it out with GMail is no longer cutting it. What are your options?

One recent option that's pretty cool for many reasons is outsourcing the sending to MailChimp. MailChimp is actually a pretty comprehensive solution for mailing lists. They will help you design your HTML email template by providing some base themes. And most importantly and perhaps underrated is that they will do their best to not get your emails flagged as spam and have your sending address blacklisted on a Real-time Blackhole List (RBL, or DNSBL). There are some 100 such RBLs which are constantly updated with the IP addresses of hosts on the Internet being used to send spam. Anything coming from those IP addresses will be flagged as spam. So you really do not want to end up on one of those lists. There are hundreds of public RBLs and you can search your mail server's IP address on them if you suspect that you're on a blacklist.

It's unlikely that MailChimp's servers will ever end up on a RBL since they would fight strongly to protect their reputation. But if you choose to run your own mail server (rather than offloading it to Google Apps for domains which is free for most small businesses and organizations) and also to use it to pump out large mailing lists then the onus is on you to set it up correctly. For example, don't let it be an open relay for anyone to send mail through. You'll also want to set up SPF records for your domain.

If you mess up and your mails look like spam to someone like Google or Yahoo or Hotmail (does anybody still use Hotmail to receive email rather than to send spam themselves?) then they will block mail from you to all of their users. Or they will get your mails but they will automatically go into their spam folders. Then you will be forced to thrust yourself into the Kafkaesque world of customer support at companies which don't have retail stores for you to visit, and which you aren't really a customer of to begin with.

First, are you sure your host allows you to send a lot of emails out? Is it your own server or VPS or a shared host? A shared host will probably rate-limit your email sending meaning it will take hours or days to send out a single email to your entire list.

Next, since you're not using MailChimp's cool interface (I really should get paid for plugging MailChimp so much even though I don't use it) you need to run some mailing list manager software.

First up is Mailman. Mailman is a GNU project. It's by hackers for hackers and thus requires perhaps more manual configuration inside config files than most non-technical people can handle. The interface is not easy to use either. Side note: There are several Drupal modules for connecting Drupal to Mailman.

An alternative to that is Phplist, "the world's most popular open source mailing list manager". OK. It's PHP and web-based, and might integrate with your existing PHP website although there's not much reason to. It's popular.

Then there's poMMo. poMMo is a basic piece of software with a decent web interface, except when there are errors. Unfortunately, poMMo didn't get fully developed before being abandoned by its developers. But somebody else has created their own poMMo project on GitHub: https://github.com/soonick/poMMo

Neither poMMo nor Mailman do click through detection so you would need another solution like a URL link shortener to create links that you can keep track of clicks on.