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Re:Custom domains now available on Substack by redm on Thursday October 22, 2020 @04:27PM (#24862928)
My guess is that they have a manual pipeline where it requires some effort from a physical person to setup SSL. This $50 is to offset their cost of setup.
Re:Custom domains now available on Substack by mattmanser on Thursday October 22, 2020 @05:59PM (#24863760)
It takes a programmer like half a day to automate a let's encrypt process, maybe a couple if you want to make it really robust.

For example, these days most wordpress hosts do this for you for free.

Not that I think it's unreasonable to charge for this, just saying it's probably not the reason.