Thanks for the link. That sounds like the most hassle-free approach for me 
(since I don't have much mail yet). I think I'll give that a shot. And I'll be 
sure to make a backup first.

PS: apologies to Aki by the way, for accidentally replying directly to you 
earlier as well. I can't get protonmail to reply to the mailing list only, 
without manually adjusting it.
Also apologies for answering above the message now, when I answered underneath 
the message first. Since I don't see a consistent style in this mailing list 
I'll use my preferred style of answering above messages from now on.

On Wednesday, February 22nd, 2023 at 00:49, Ben Burk <b...@burk.tech> wrote:


> I would definitely get mail-crypt working on your system before worrying
> about encrypting existing emails. Iirc dovecot should support both types
> of files (encrypted, and non-encrypted) concurrently. So BEFORE you try
> anything, make sure via logs, etc that mail is being written to the fs
> as an encrypted file and that dovecot is able to decrypt it (i.e. you
> are able to view that particular mail file from your email client).
> 
> My specific use case way back was to encrypt a maildir system using this
> plugin a year or so ago. I believe there are 2 ways to set mail-crypt
> up. Using global keys or folder-specific keys. What you will learn going
> through this process using folder-specific keys is that any time mail is
> moved (from an IMAP directory to another) the mail becomes effectively
> re-encrypted using the destination's folder keys. I imagine how this
> works under global keys is that the mail is encrypted once when it is
> moved, then never again unless keys change. So all you would need to do
> to encrypt existing mail using either method would be to create a temp
> imap folder, move mail from each IMAP folder one at a time into this
> temp folder, then back to the original IMAP folder.
> 
> I had a few questions at the time in implementing this, so I've linked
> here the dovecot mailing list thread so it might provide some context if
> needed:
> 
> https://dovecot.org/pipermail/dovecot/2021-July/122469.html
> 
> 
> On 2/21/23 16:29, Jeremy wrote:
> 
> > On Tuesday, February 21st, 2023 at 09:54, Aki Tuomi 
> > aki.tu...@open-xchange.com wrote:
> > 
> > > > On 16/02/2023 07:18 EET mailinglist-subscriptions 
> > > > mailinglist-subscripti...@protonmail.com wrote:
> > > > 
> > > > Hi,
> > > > 
> > > > I am using dovecot 2.3.16, along with postfix and a PostgreSQL database 
> > > > for managing virtual accounts.
> > > > 
> > > > I'd like to start using the mail-crypt plugin. However, I'm having a 
> > > > bit some difficulty understanding the documentation at
> > > > 
> > > > https://doc.dovecot.org/configuration_manual/mail_crypt_plugin
> > > > 
> > > > to reach my goal. I plan to ask questions about those issues by 
> > > > starting new threads in this mailing list. But before I even come to 
> > > > that, I'd like to investigate the following:
> > > > 
> > > > The above documentation only addresses a clean install and doesn't seem 
> > > > to mention encrypting already existent unencrypted mails, like my 
> > > > server has. Is it possible to encrypt those before I start using the 
> > > > mail-crypt plugin, such that it will be able to decrypt those messages 
> > > > as well?
> > > > 
> > > > If it is, I am assuming that how I would go about achieving that will 
> > > > be very dependent on the ultimate configuration I have in mind 
> > > > (pub/priv keys, etc.). So I don't expect a full-fledged guide. However, 
> > > > if you could perhaps give a general overview of what would be needed to 
> > > > achieve this, I would very much appreciate that.
> > > > 
> > > > Thank you.
> > > 
> > > It will be easiest to do migration to new server, then the data will get 
> > > encrypted while migrating. It is possible to write a script to do this, 
> > > but will be much more hassle than migration.
> > > 
> > > You might even be able to do it for one user at a time, by doing 
> > > migration from maildir to maildir and then moving the new maildir over 
> > > the old one.
> > > 
> > > Aki
> > > Thanks for the suggestion. However, migrating sounds like quite the 
> > > hassle as well.
> > 
> > Now, I have next to no knowledge about the synchronization workings of 
> > IMAP, so perhaps this is totally infeasible, but could the following work?
> > 
> > - Preface
> > I am the only user of the mail server, with one virtual catch-all account 
> > for each domain I own. I access these accounts with Thunderbird.
> > 
> > - Solution
> > I make a backup of all mail in my Thunderbird accounts. Then I either 
> > delete all mails from within Thunderbird, or on the server. Then I 
> > configure the mail-crypt plugin. And then I import all backup mails and 
> > folders into my Thunderbird accounts again?
> > 
> > Could that work? Or would that mess up the synchronization history (message 
> > IDs and what not)? And most importantly, if it actually could work, would 
> > the messages be properly encrypted then?

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