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?
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Just get the f out of gmail. Almost anything else is better. Dont hold off for perfection as it doesn’t exist. I use Proton and Tuta. I won’t renew Proton because CEO is a wanker. Migration to Tuta was good and they have Tuta calendar.
I read somewhere tuta is just a honeypot though.
Please can you support the honeypot comment? Both Privacy Tools and Privacy guides and others recommend it. There is a reasonable free tier and a paid tier. I don’t see the honeypot.
That’s the thing. It’s mostly just Reddit shit. Nothing proven but the case they made is plausible so…I dunno.
I recently started migrating my email and went with mailbox.org. I opted for it based on it having a good balance of ethical/environmental stances, support for custom email domain (so email doesn’t feel like vendor lock in in the future), and a business model focusing on paid service.
There were a lot of options but ultimately I just wanted something “good enough” rather than spending weeks on comparing. A part of that decision was realizing I didn’t care about getting something with the best possible privacy - email is predominantly an insecure medium and things with E2EE work only if the recipient is in the same ecosystem, which is rare. In practice I’m not going to trust anything sensitive to email regardless, so I might as well prioritize picking something that looks like a decent and stable balance.
Mailbox.org has calendar but I haven’t really played with it much. I’m realistically going to look in to look in to something self hosted since I will require more features than most email providers will offer, so I don’t want to tether the two services. That was a part of the reasoning for Mailbox.org over something with more services - I wanted email, not something trying to be the next ecosystem - that’s what I was trying to get away from!
Whichever service to decide to switch to I’d recommend not deleting your gmail, just let it rot, you never know if you need access to that email again.
I’ve been using purelymail.com, $10 a year gets me just what I need, which is as many independent addresses and inboxes as I would reasonably need under a parent account. It is what it says on the tin, so there aren’t any extras like file storage. Granted, there is a bus factor associated with Purelymail since it looks like a one-man operation for now.
I’m not qualified to speak on cloud-based calendars since I design and print my own.
The one thing that stood out about Purelymail to me was having not just aliases, but fully separate inboxes. But I’d also suggest checking out Tuta, Posteo, mailbox.org, and FastMail. I had also used Proton and was considering upgrading my plan. What kept me back was the web interface getting heavier by the year and having to install Bridge to use another client wasn’t my cup of tea. E2EE is certainly a good feature, but I’ve never found myself sending an email to another Proton user and therefore have never taken advantage of it.
Proton and Tuta email and calendar are free. Might as well give it a go.
A managed NextCloud instance is also a good option (but nothing is encrypted).
Use either Tuta or ProtonMail (I use both) with SimpleLogin aliases 
I. like the idea of simplelogin as it seems to do what I’m already doing with icloud plus but it suffers the same problem. the messages are flowing through a third party before they get to me. why would I trust a third party?
FWIW, Proton has acquired SimpleLogin. As such, I perceive/regard it as an extension to Proton rather than a third party.
Whatever your choice, go for one that supports personalized domains – and buy your own.
That way it’ll be less of a hassle if you need to change provider later.Coming up with a decent domain name has been the challenge for me. You can’t really put on to your cv or so something like me@thebestmfofalltime.com. You can but that doesn’t sound very professional.
