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At the very least, I can confirm that ProtonMail and Apple's Mail clients let you search through the message contents of encrypted email. I'm sure there's a per

At the very least, I can confirm that ProtonMail and Apple's Mail clients let you search through the message contents of encrypted email. I'm sure there's a performance hit, and admins wouldn't be able to search through the encrypted emails of their Workspace users, but that's a much more reasonable tradeoff.

londons_explore 4y ago
I'd be interested to know the implementation... Most search-over-encrypted-documents implementations either don't scale well (eg. require the client to do all the indexing and upload the encrypted index), or have reduced privacy (allowing the server to infer which words are in which document).
- JoshTriplett 4y ago
  > require the client to do all the indexing and upload the encrypted index Or just require the client to do the indexing and the searching, and not upload the index anywhere.
  - prophesi 4y ago
    Yep. Not sure how Apple/Proton implement it, but that's exactly what Tutanota does. https://tutanota.com/blog/posts/first-search-encrypted-data https://tutanota.com/blog/posts/first-search-encrypted-data
  - londons_explore 4y ago
    And when you log in from a new device...? Do you now need to wait days while 1000,000 emails from the last decade are all downloaded and indexed?
    - prophesi 4y ago
      That's an issue with or without client-side encryption. Even with IMAP, you have to download the message before its contents can be searched. While subject/sender/recipient can be searched instantly with IMAP, regardless of encryption.
      - pseudalopex 4y ago
        This is a limitation of your client or server. Not IMAP.
        prophesi 4y ago
        No, it's a limitation by IMAP that is rectified by the server/client.
        pseudalopex 4y ago
        IMAP's SEARCH TEXT command is at least 35 years old.[1] [1] https://datatracker.ietf.org/doc/html/rfc1064 https://datatracker.ietf.org/doc/html/rfc1064
    - pseudalopex 4y ago
      Maybe if you have that many emails and 3G only and can't load a backup for some reason.

londons_explore 4y ago

I'd be interested to know the implementation... Most search-over-encrypted-documents implementations either don't scale well (eg. require the client to do all the indexing and upload the encrypted index), or have reduced privacy (allowing the server to infer which words are in which document).

JoshTriplett 4y ago
> require the client to do all the indexing and upload the encrypted index Or just require the client to do the indexing and the searching, and not upload the index anywhere.
- prophesi 4y ago
  Yep. Not sure how Apple/Proton implement it, but that's exactly what Tutanota does. https://tutanota.com/blog/posts/first-search-encrypted-data https://tutanota.com/blog/posts/first-search-encrypted-data
- londons_explore 4y ago
  And when you log in from a new device...? Do you now need to wait days while 1000,000 emails from the last decade are all downloaded and indexed?
  - prophesi 4y ago
    That's an issue with or without client-side encryption. Even with IMAP, you have to download the message before its contents can be searched. While subject/sender/recipient can be searched instantly with IMAP, regardless of encryption.
    - pseudalopex 4y ago
      This is a limitation of your client or server. Not IMAP.
      - prophesi 4y ago
        No, it's a limitation by IMAP that is rectified by the server/client.
        pseudalopex 4y ago
        IMAP's SEARCH TEXT command is at least 35 years old.[1] [1] https://datatracker.ietf.org/doc/html/rfc1064 https://datatracker.ietf.org/doc/html/rfc1064
  - pseudalopex 4y ago
    Maybe if you have that many emails and 3G only and can't load a backup for some reason.