I don't know if you are able to use the Ledger Nano S wallet with Electrum. On
its page electrum is missing. The
ordinary Ledger Nano got it. I only go the normal Ledger Nano, it is not possible for me test it.
I don't know if it is optimal to run a chrome app, as you need to connect a google account to it and it might reveal your identity. Instead you might be able to download
Copay and install it inside of TAILS, as the Ledger Nano S supports Copay. I got no TAILS drive, so I can't test it. (I might be able to boot a TAILS VM and test it)
I'm not sure if it's possible to install external applications into TAILS? Electrum is preinstalled so I figured I should use that. But it sucks if the Nano S does not support Electrum. So what options do I have for retaining privacy while using the ledger nano s? Is it possible to use it without TAILS but still routing all traffic through Tor? Or would I be better off storing my bitcoins in Electrum on a regular TAILS drive?
Thank you both for taking time to reply. It's much appreciated!
I'm not a TAILS expert, so I don't know if it is possible to install external programs on TAILS. If you aren't able to do it, it completely removes all options of using your Ledger Nano S, as it requires either Chrome or Copay. (As explained above).
If you are able to install Copay (Which is preferred over a chrome extension) on an OS (Preferable a Linux distribution) and route all network connectivity via Tor, you should get 99% of your concerns privacy. Not quite as good as running directly onto TAILS.
About the second solution, that would be possible. You just need to make sure you got a secure way to import your private key(s) into Electrum each time you want to sign a transaction/message. (as it deletes your session every time you reboot) It covers your privacy better, but it is less secure. It wouldn't work as a cold storage, as your private key(s) could get compromised.
I don't know if it would work, but you could try trading your Ledger Nano S for either an Trezor or a Ledger Nano S. (Just my 4 cents)