I’m considering finally jumping off gmail. I’m not going to host my own email since I just don’t have the skill to secure that thing well enough myself. Any mail server I set up would become a botnest within hours. So that has me looking at third party stuff.
Proton has a mostly good reputation, though their CEO’s twitter post a while back praising the Trump regime makes me question if I should trust them with anything. I don’t know enough about the entire situation to know if its just internet drama or a real concern, but anything involving Trump is a huge red flag for me.
Tuta looks pretty nice but I’ve read there are concerns about it being in a country that’s part of the 14 eyes collaboration, so it might not matter what the organization wants if the government of the region they are in says fuck off and do what we tell you.
On the lower end of concerns, I am in the Apple ecosystem. (boo hiss I know). I like the clean and simple built in apps like email and calendar and how the notifications all work across my watch, phone, mac and homepods. I like how safari can just jump in and throw an email alias at things for me. I like how all my stuff is managed. But I also know Apple could piss me off at any moment and make wild sweeping changes I might not like, so relying on them too much could screw me over someday. I dont know, right now I really like their setup but portability does seem to matter more ultimately so this switch does seem like a better idea in the long run, even if I’m giving up features I may enjoy.
What are your opinions on the privacy email and calendar services in 2025? Should I even both with a cloud based calendar in the first place?
If you’re willing to pay for it, Mailbox.org would be my choice. No provider will give that feature away for free (which I’m sure you know). My threat model can tolerate an extra hand via Addy, so I don’t mind them being there.
But no matter who you choose, email just isn’t the best option for true privacy. There will always be some cleartext email somewhere in the process, even if only sometimes. And as somebody once said, “No company is going to break the law for you.”
If you need an extra level of privacy with email specifically, your best option is to self host. That way you control both the server and the database/storage.
I wont self host email. I just don’t have the skill to properly protect a public-facing server. I’m smart, but only enough to know I’m outgunned there. I’m not running some grand criminal enterprise. It’s more of a concern that I’ve been a bit lax in my online privacy and with the worldwide rise in fascism, I feel I need to resist (or at the very least, inconvenience) those who could do me harm.