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I'm working with some sensitive data, and want it as secure as possible - that said, I'm pretty un-technical, so am trying my best to figure this stuff out.

My setup is;

USB stick encrypted with bitlocker - encrypted volume made with Veracrypt inside the encrypted USB - and am running Tails through Virtual Box from the Veracrypt container.

1, I have no idea if this is safe or not (i couldn't get tails to boot from multiple USB's, no matter how hard I try

2 - Is there a way with my current setup I can make a persistent volume with Tails, so I don't have to manually import a PGP key each time?

Thanks

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    That looks like not a great setup. You should focus on getting tails to boot before handling sensitive documents. Don't run Tails inside a VM.
    – cacahuatl
    Aug 8, 2016 at 17:13

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To boot from USB you will need to change the boot options on your computer either via BIOS or UEFI settings and change priority to boot usb first or select it from the boot start options list for a one time USB boot as necessary. Depending on the brand and hardware, a secure boot mode may be enabled that you will have to disable or turn on legacy boot mode to get this to function properly.

I would definitely not run Tails from a VM for operational purposes other than testing as this would defeat the security of what Tails is meant to do in the first place.

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  • Indeed, the step of the installation guide that tells you to boot tails has a troubleshooting step that explains this: See step 4/7 and click on the link in the link saying "refer to the troubleshooting section about Tails not starting at all."
    – cacahuatl
    Aug 8, 2016 at 22:08

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