I'm looking for an easy way to set up a simple IM infrastructure that protects messages in transit as well as avoids having logs in places that neither I nor someone I trust controls. I'm based in Germany and according to Mr. Snowden, my traffic actually gets sifted through and analyzed, and I'm not comfortable with that at all. IM is something that bugs me a lot in that regard.

I'm thinking about having an isolated XMPP server with accounts for everyone in the group of people who needs this, and to require SSL with self-signed certificates. I'm running an XMPP server on my raspberry pi anyway, so why not pimp it with some SSL security. It's configured to not write any logs except for errors and diagnostics, so the log issue is fixed there already. The people in question know how to use Pidgin, but anything overly annoying wouldn't fly with any of them. Mobile would be a requirement as well, Facebook's just too convenient. I think XMPP has that covered.

I'm not so fond of OTR, as the Pidgin plugin requires a decent bit of technical literacy, crashes Pidgin every once in a while and takes 10+ seconds to initiate a conversation (for me) during which Pidgin completely freezes. Also, as far as I know there's only IM+'s plugin for mobile platforms and is quite pricey. Relying on a self-hosted server and SSL certificates should work for all conceivable platforms (I guess?), be relatively easy to set up on the client side and provide a decent improvement in security.

The question is, would that be safe enough? At the very least I aim to keep my communication over this infrastructure out of the NSA databases. I'm not aiming to withstand any directed attack by trained experts or the like, I'd just like to have private conversations that actually are as private as a phone call once was, and not archived and analyzed somewhere else as a matter of routine.

If it is, another side question, any recommendations on how exactly to generate the certificates to make them secure? I read that some algorithms may have been compromised, I'd like to avoid those if possible. I've seen a few threads on here on that, but none (that I understoof) with that NSA-proofness spin.

I'm pretty new to all of this, so some (newbie-friendly) background reading would be appreciated, too.

Thanks!

I'm looking for an easy way to set up a simple IM infrastructure that protects messages in transit as well as avoids having logs in places that neither I nor someone I trust controls. I'm based in Germany and according to Mr. Snowden, my traffic actually gets sifted through and analyzed, and I'm not comfortable with that at all. IM is something that bugs me a lot in that regard.

I'm thinking about having an isolated XMPP server with accounts for everyone in the group of people who needs this, and to require SSL with self-signed certificates. I'm running an XMPP server on my raspberry pi anyway, so why not pimp it with some SSL security. It's configured to not write any logs except for errors and diagnostics, so the log issue is fixed there already. The people in question know how to use Pidgin, but anything overly annoying wouldn't fly with any of them. Mobile would be a requirement as well, Facebook's just too convenient. I think XMPP has that covered.

I'm not so fond of OTR, as the Pidgin plugin requires a decent bit of technical literacy, crashes Pidgin every once in a while and takes 10+ seconds to initiate a conversation (for me) during which Pidgin completely freezes. Also, as far as I know there's only IM+'s plugin for mobile platforms and is quite pricey. Relying on a self-hosted server and SSL certificates should work for all conceivable platforms (I guess?), be relatively easy to set up on the client side and provide a decent improvement in security.

The question is, would that be safe enough? At the very least I aim to keep my communication over this infrastructure out of the NSA databases. I'm not aiming to withstand any directed attack by trained experts or the like, I'd just like to have private conversations that actually are as private as a phone call once was, and not archived and analyzed somewhere else as a matter of routine.

If it is, another side question, any recommendations on how exactly to generate the certificates to make them secure? I read that some algorithms may have been compromised, I'd like to avoid those if possible. I've seen a few threads on here on that, but none (that I understoof) with that NSA-proofness spin.