Transactional Email vs Corporate Email

Know your email -

Everyday we all get tons of email… Most want to sell us things (Marketing), some confirm that we did something (Transactional), and most rare of all… personal or business correspondence.

One perk of being a not-for-profit institution is “free” email services from Microsoft (O365) or Google (Gmail). Free is relative as there is always limitations. O365 and Gmail are great for sending business and personal correspondence. These services get really, really unhappy with organizations trying to send Transactional or Marketing emails. This unhappiness comes from recipients flagging emails as junk or blocking messages as it lowers the trustworthiness of the service that is sending your email out.

How does this apply to TM? TM potentially sends hundreds if not thousands of emails each month to a variety of patrons for a variety of reasons. If you try sending this type of volume through Gmail or O365, they will block you. This is not the type of service they are offering. It has nothing to do with TM as a product. TM is only sending the number of emails your organization has asked the software to create.

There are a number of transactional email service providers, all have their benefits and their drawbacks. Mailbakery has a reasonable list of the most common providers and some of their pros and cons. Again, you will run into cost for more features.

We have spent the last two years using Mailgun. It is not the fanciest, but you cant beat the price. The first 10,000 messages per month are free and from there to just over a million messages are 0.0005 cents per message. Quick math… 1 Million messages would be a maximum of $500.00 per month.

While it is not a drawback for us, the messages will send from a subdomain of your domain. For us our business emails come from and TM emails come from Within mailgun, we have all messages, i.e. replies, that go to an email address ending in forward to our box office general account We never miss a reply from one of our transactional emails.

The setup is relatively simple. My biggest complaint about Mailgun is their help documentation. At the end of the day, the product is designed for implementation by a developer, so the documentation assumes you know a lot.

Regardless of vendor, to implement any transactional service, you will need access to your website’s DNS records. If I hadn’t lost you already, that last sentence probably did it. A Domain Name System record is effectively the translation of a website’s IP address to a friendly name… is nowhere near as useful as The service will require you to add some data to confirm that you own the name and to encrypt your messages.

I personally fought TM for YEARS on the idea of outsourcing transactional emails. As Microsoft and Google tighten down the free services they offer to person to person emails most users will need to look for an alternative for sending transactional messages.

TM is not to blame for breaking your email, you are asking your email provider to perform a function that may be out of scope.


Very helpful explanation Randale - thanks!

Update: Bonnie graciously gave us a call and we’re looking at some options!

Sorry to bump this thread - it seemed better than starting a new one.

Thanks for the info Randale! I’m finally looking at getting Mailgun implemented and this was a helpful launching point.

I am having some troubles getting it going though. Currently just in their sandbox mode to try it out and I can’t seem to get a test email out through TM. Seems like I’m failing to even login/authenticate. I’m just in my own employee preferences, didn’t want to test it company wide until it’s actually ready.

Any tips on something I may be overlooking? Or mind sharing some of your SMTP settings?