Discourse not sending Emails to All Users in mailing list mode

How much RAM do you have? Do you have swap? How big is your database?

This is the problem that you want to solve.

I have 4GB, which should be more than enough to handle a single Discourse site? Not sure if there is any/how much swap on the Digital Ocean shared plan ($20 a month)

That should be enough unless your database is huge. If you have resized your droplet since you installed you should run discourse-setup again to reset the memory parameters (or edit app.yml yourself).

Do the mail logs in admin / mails /logs / sent|skipped show that the messages are being sent?

Do the mail provider logs show the 15 messages or a bunch more that it hasn’t delivered for some reason?

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