Skiff – Privacy-first end-to-end encrypted email

Re:Skiff – Privacy-first end-to-end encrypted email by Youden on Wednesday August 23, 2023 @05:59AM (#37233780)

After getting fed up with ProtonMail recently I went on a quest to find an alternative. Unfortunately Skiff doesn't have SMTP or even an export feature so once you go Skiff you can't go back, you're locked in.

ProtonMail does have import/export and the SMTP bridge (for paid users) and those things work but ProtonMail mangles emails: it removes plaintext body where there's a HTML body and it screws with headers.

Ultimately the best option I could come up with was self-hosting my email address. Incoming emails go directly to a box sitting in my office, with TLS enforced.

I put this off for years fearing deliverability issues but finally realised that incoming and outgoing email can be hosted in different places. So though the box in my office receives my email, I send email through either a Hetzner box or Mailgun (with retention disabled). Haven't encountered any issues with this so far.

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Re:Skiff – Privacy-first end-to-end encrypted email by taskforcegemini on Wednesday August 23, 2023 @06:38AM (#37233983)

> After getting fed up with ProtonMail recently I went on a quest to find an alternative. Unfortunately Skiff doesn't have SMTP or even an export feature so once you go Skiff you can't go back, you're locked in.

wow, an e-mail service without smtp nor imap?? no thanks

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Re:Skiff – Privacy-first end-to-end encrypted email by jacooper on Wednesday August 23, 2023 @08:56AM (#37235113)

You can't have SMTP if it's fully end-to-end encrypted. That's why proton has a bridge, it decrypts messages locally, then runs an SMTP server for your local clients.

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Re:Skiff – Privacy-first end-to-end encrypted email by prophesi on Wednesday August 23, 2023 @09:18AM (#37235413)

You can if the service doesn't handle encryption with a proprietary protocol and instead helps you set up PGP. It certainly has its issues and limitations, but after trying ProtonMail/Tutanota/what-have-you, I have _never_ actually used their E2E encryption except when contacting support for that mail service.

Meanwhile with PGP I can post up my public key on my personal sites / resume / social accounts, and people actually have reached out. I also like that you don't even need to include your email address to prevent scrapers from harvesting it. If it's on one of the public keyservers, their client will find the email address for the respective public key.

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Re:Skiff – Privacy-first end-to-end encrypted email by intc on Wednesday August 23, 2023 @10:08AM (#37236146)

One can use standard IMAPS/SMTPS/PGP compliant native email app with C1.FI.

I'm still contemplating about the E2E webmail app - No matter which way one looks it - It's a shaky concept...

BTW. Does anyone know what is the current state of WASM Constant Time proposal?

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Re:Skiff – Privacy-first end-to-end encrypted email by c7DJTLrn on Wednesday August 23, 2023 @09:27AM (#37235533)

Well, ProtonMail isn't end-to-end encrypted anyway, even with Bridge. Unless you use PGP encryption. Emails are encrypted in-flight with TLS, but ProtonMail terminate that TLS connection.

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Re:Skiff – Privacy-first end-to-end encrypted email by jacooper on Thursday August 24, 2023 @05:01AM (#37246581)

I'm talking about zero knowledge encrypted email storage. Proton mail doesn't have access to your messages, and SMTP doesn't support that type of encryption.

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Re:Skiff – Privacy-first end-to-end encrypted email by amilich on Wednesday August 23, 2023 @12:41PM (#37238703)

We do have export to EML and ZIP files. SMTP/IMAP are not trivial due to end-to-end encryption.

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Re:Skiff – Privacy-first end-to-end encrypted email by jvan on Wednesday August 23, 2023 @08:50AM (#37235024)

Do you have a write-up about this? I've been wanting to host my own almost entirely for the extra control over incoming mail and have been held back by the same worries. I'd like to see what a success story looks like.

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Re:Skiff – Privacy-first end-to-end encrypted email by Youden on Wednesday August 23, 2023 @12:23PM (#37238405)

I don't, sorry. The short story is that I use Docker Mailserver [0] with some customised config for SMTP relaying, spam filtering and Gmail fetching with spam filtering. I also have a Roundcube container.

Underneath though, it's a pretty standard Postfix + Dovecot setup and there are plenty of those around.

[0]: https://docker-mailserver.github.io/docker-mailserver/latest...

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Re:Skiff – Privacy-first end-to-end encrypted email by JeremyNT on Wednesday August 23, 2023 @03:22PM (#37240926)

I could recommend Fastmail with PGP (when it matters). They have good documentation on how to do this [0].

More expensive than self hosting, but still quite cheap, and no weird vendor-specific lockin for the important parts.

[0] https://www.fastmail.com/blog/pgp-tools-with-fastmail/

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