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Here’s my old project on it:
https://github.com/brianddk/trezor-tails
Wiki explaining it:
https://github.com/brianddk/trezor-tails/wiki
Here’s the CURRENT work on it:
https://github.com/trezor/trezor-suite/issues?q=is%3Aissue+tails
I’d say most of your issue is going to be getting the bridge module working since WebUSB doesn’t work on tails. I got it working but it was many many years ago. The work on bridge might still be effective after all that time. IDK.
Once bridge is working, Suite has a native Tor setting that should work. I found that most conflicts (with other products) were CDNs that would veto any TOR traffic. By war-dialing bridges I could eventually, through perseverance and luck, find one that the CDN didn’t block.
In the end, more trouble than it was worth. But if your highly motivated it is certainly doable.