Selfhosted
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I haven't actually used the embedded postfix server at all, I keep mine disabled. I only include it because it's "included" in the official Docker deployment files, and I try to keep this deployment as close to that as possible.
I'm considering adding support for an external email service, as you mentioned, but I have nearly zero experience in using managed email services, and I'm not sure if non-technical users would be able to navigate the configuration of things I can't do for them (i.e. on a web dashboard somewhere). And if I can't do it for them, it means more issues for me, so I hesitate to add support for it at all.
I'd love to hear your experience in setting up sendgrid and how easy that was. And the tracking stuff you mentioned as well.