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Is it possible to encrypt a bootable drive?

Started by KevinMeehan , Mar 10 2017 05:06 AM

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5 replies to this topic

#1 KevinMeehan

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Posted 10 March 2017 - 05:06 AM

Hello all,

I've been a Mac user all my life. Recently, I built a Windows 10 PC and love the OS. I decided to buy a TB external hard drive on Amazon and create a bootable HDD to run Windows on my Mac when I want to (BootCamp doesn't work on my Mac), which I successfully did.

My Mac is encrypted with FireVault (Apple's built-in encryption software) for general safety. I'd like to do the same with my bootable external hard drive running Windows 10.

My question is, is this possible? Will the Mac recognize an encrypted external hard drive at the boot menu? If it did, would I just have to enter the password immediately and then boot Windows?

Say it is possible to encrypt a bootable external HDD. How would I do it? Would I use a Windows software within the bootable WinOS, or would I use FireVault from the Mac?

Thanks a lot. - Kevin.

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#2 technonymous

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Posted 10 March 2017 - 07:59 AM

Hello Kevin,

Have a read...

http://lifehacker.com/format-encrypted-drives-as-exfat-to-make-them-play-nice-1778982194

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#3 Didier Stevens

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Posted 11 March 2017 - 05:48 AM

This article explains how to create a TrueCrypt (and by extension VeraCrypt) container on an ExFAT disk.

Such a container can not be used to boot Windows.

Edited by Didier Stevens, 11 March 2017 - 05:49 AM.

Didier Stevens
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SANS ISC Senior Handler
Microsoft MVP 2011-2016 Consumer Security, Windows Insider MVP 2016-2019

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#4 th3k3rst

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Posted 13 March 2017 - 02:05 PM

This can be done with PGP whole disk encryption, I think. I'm not sure how this would work with the dual boot scenario.

I found this, too. It talks about a dual boot, but with windows installed on a partition vs your separate external drive...

https://www.ahrenstein.com/blog/dual-booting-encrypted-windows-and-encrypted-os-x/

This is actually interesting to me. I would like to hear how this is going for you. LMK if any of my suggestions help, too! I've never done this so I'm just kinda shootin ya ideas

GOOD LUCK!

If youre using win to go, cant you just use bitlocker?

I saw your post at cnet saying you were using win2go.

https://technet.microsoft.com/en-us/library/jj592680(v=ws.11).aspx#wtg_faq_bitlocker

Edited by th3k3rst, 13 March 2017 - 03:22 PM.

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#5 technonymous

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Posted 14 March 2017 - 11:17 AM

This article explains how to create a TrueCrypt (and by extension VeraCrypt) container on an ExFAT disk.

Such a container can not be used to boot Windows.

Sorry for the misunderstanding, but I wasn't suggesting booting the exfat drive. I was suggesting keeping each os in their normal supported format or dual boot, but have a separate partition formatted in exfat. This way both OS's can mount and share the exfat drive and have the ability to encrypt files with Veracrypt that runs on MAC, Windows and Linux. If the OP wants full disk encryption and ability to share files between MAC and Win then each os will still need to be separated and running their native encryption individually (bitlocker) etc and then still make a volume partition in exfat to be shared and mounted with veracrypt. Maybe there is better solutions out there.