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I've been sending text html emails for my blogletter for over a year now. The single biggest struggle point is the spam filters in gmail/outlook/others which just render my emails waste for majority of the subscribers.

Do you face the same?

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I think I recall from a previous post on HN that they use Mailgun. I can't speak for forlater but at my work we use mailgun because email delivery is a pain, as you've found. Using a third-party service is a lot easier because it's their bread and butter and you can let them worry about it.

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