Establishing a flexible mailer option

[Shpigford]

The app has two "needs" to fill for mailing.

1. Self-hosters who have very simple, low-frequency mailing needs (at most 1 email every day for something like a financial report)
2. Maybe's hosted option where we're sending many thousands of emails every day (and 🤞 many multiples of that down the road)

What's a low-hassle way to meet both of those needs on the backend such that the average self-hoster ideally isn't needing to sign up for a paid external service but also that's flexible enough so them or us can plugin the mailer of our choice?

[shobhitic]

Most mailers provide SMTP settings. Can use the SMTP settings from environment, that way we can use the same code for both environments.

By default we can set something that has a free tier (like resend, or SES) and ask the user to only change username/password for their installation.

Alternatively, can also install sendmail with docker for default scenario. The mail might be suspicious/end up in spam, but they can mark it safe as the user is only sending mail to themselves.

[jclusso]

I would suggest Postmark. They have great deliverability, straight forward Rails integration, and a free plan for 100 emails per month. This would solve both problems, if signing up for a service that is free is ok.

[Shpigford]

Small thing, but they require a "business email address" to sign up. Meaning you have to have your own domain to sign up from (no @gmail addresses).

[jclusso]

Ugh, that's so frustrating! I didn't know that.

[jclusso]

The only other alternative I can think of is people use Gmail. The configuration isn't too complex, but soon Gmail will stop allowing password auth and then it would require the user get an OAuth token which is a PITA. We could provide a script to do that maybe?

Based on the fact that the 37signals completely avoided using email for anything in Campfire, I'm guessing there is no other "clever" way.

config.action_mailer.delivery_method = :smtp
host = 'example.com' #replace with your own url
config.action_mailer.default_url_options = { host: host }

# SMTP settings for gmail
config.action_mailer.smtp_settings = {
  :address              => "smtp.gmail.com",
  :port                 => 587,
  :user_name            => <gmail_username>,
  :password             => <gmail_password>,
  :authentication       => "plain",
  :enable_starttls_auto => true
}

[shobhitic]

@jclusso I am using 2 factor auth right now, I already can't use email and password. I think they have something called oauth token that can be used in some kind of a format with Rails (remember doing it long time back)

[jclusso]

It was called app passwords at one point.

[nilansaha]

I would recommend Resend. They have to sign up for it but their free plan is good enough for this use case

[jasonmccay]

I'd recommend Enveloop. Granted, I am a founder, so a bit biased. ;)

We have a free plan where you can use your personal Gmail account via SMTP -- it's simple to set up, plus, in addition you get a really nice visual email builder, logging, and webhooks. You don't have to set up a domain (like you'd need to do with Resend or Postmark) -- of course, you can still set up a domain on us too, and we'll send your emails for you. Magic. 🪄

Link: Docs for setting up Enveloop and Gmail SMTP

I'd love to help.

[jclusso]

In your docs it says to generate an app password for Gmail. From my understanding this is going away. Are you guys going to switch to OAuth?

[jasonmccay]

Correct -- rolling that out is on our roadmap, but for now, we are still using App Passwords. Google will be disabling App Passwords in Sept 2024.