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For many months, I’ve been dual-booting my desktop PC between Windows 11 and Ubuntu Desktop. I had to remove the Ubuntu Desktop boot, but why?
As the discerning regular reader of this esteemed blog (no-one) will know, I’ve had a bit of a dalliance with Linux Operating Systems, both in a virtual environment and “for real”, by dual-booting with my Windows 11 installation. I’ve catalogued most of the ups and down of it right here on this very website.
I ended up at a point with Ubuntu Desktop 24.04.2 where I could comfortably perform 99.99% of the tasks I used Windows 11 for, with no issues or irritations. I’d discovered that Oracle’s VirtualBox is far superior to VMWare, I’d found some fairly acceptable Linux equivalents of my favourite Windows programs to use – I even softened to the point of using LibreOffice Calc without crying or any gnashing of teeth. I’d found a really good sync program (InSync) that even let me use OneDrive natively on Linux, as if it was.. well, OneDrive.
I’d go quite long periods of time using Ubuntu before switching back to Windows 11. So what happened?
Well, it was like this, Guv
Once I’d finished mucking around with IPv6 (and I documented that foray into “21st Century” technology, too), my attention turned back to trying to rid myself of big tech company reliance. I’d already got rid of Amazon Web Services and turned a weepy, slightly jaundiced eye towards Microsoft. I was unhappy with Outlook in particular, dur to the fact there was no Linux client (there used to be, by the way) and it had become a bit over bloated.
I’d also discovered that my note-taking app (Joplin) was saving file attachments in an unencrypted area of disk drive (on Windows 11) and so I decided to do something about that. That something was to enable BitLocker encryption on the Windows drives that held my data. That meant enabling for the system drive (C:) and the disk where I keep my data, let’s call that D:.
And that was when things took a turn for the worst.
Please enter your BitLocker Key… again and again and again…
I’d been here before, so I had the presence of mind to make a note of the BitLocker encryption key when I turned BitLocker on for the C: drive.
The Surface Pro
In fact, I’d tried the whole dual-boot with BitLockered Windows 11 and Ubuntu Desktop before. It was on a Microsoft Surface Pro 8; I’d managed to squeeze a partition out of the disk and installed Ubuntu Desktop with some success. On reboot, it asked for the BitLocker key (which you have to enter manually) and then it would boot. It only asked for the key once and all was well. I eventually removed Ubuntu, as it was requiring far too much work for me to configure that I cared to give it. But it did work.
The main desktop workstation
The main desktop (as I’m calling it) was – shall we say – uncooperative. On reboot, it presented the grub bootloader options (Windows or Ubuntu boot) and would boot into Ubuntu with no issue. Windows was not having it. Every time I tried to boot to Windows, it would ask for the BitLocker key. Every single time, dammit!
Once I’d enter the key, it would boot to Windows just fine. But then on reboot, it forgot it! Over and over.
Troubleshooting
Now I’m not 100% sure about this (as I couldn’t be arsed to look it up at the time), but the main difference between the Surface Pro (that did work) and the main desktop (that didn’t) was that the Surface Pro already had BitLocker encryption on it when I installed Ubuntu. The main desktop was not encrypted when I installed its Ubuntu. I suspect that something in the boot loader on the main desktop (which is grub) didn’t like the fact that it couldn’t read the newly encrypted Windows disks, I’ll be bound.
I seem to recall (ages ago) that if BitLocker was enabled (and therefore secure boot), you had to reinstall Ubuntu to regenerate the boot loader. This may be complete bollocks, but it was enough for me to remove Ubuntu – at least for the time being.
And in the future?
I’ve left all the disk infrastructure in place for Ubuntu, so once I’ve sorted out my various encryption and security thingies, there’s the possibility that I can resume and rebuild an Ubuntu desktop. Which will happen at some point. For the time being though, I’ll carry on with Windows 11.
A Postscript
It’s been almost two weeks since I finished writing the above verbiage and am now writing this paragraph as a P.S.
In that time, I’d thought about Linux disk encryption and decided to delve a little deeper into it. I was already aware it was possible, the point was could I dual boot it with a BitLocker-ed Windows 11?
The answer is of course yes, however it does take a bit of faffing to achieve it. The are plenty of articles around on the internet for guidance; some better than others, but after a week or so of experimentation with a virtual machine, I found that the easiest (not necessarily best) method to achieve it was to let the Ubuntu installer do the work for me.
If there’s already a BitLocker-ed Windows system partition (which I have), I found it better to turn BitLocker off, then extend the Windows partition enough to allow the Ubuntu installer to shrink it and install Ubuntu. A bit backwards I know, but it works and it’s a lot less messing around with partitions drives, logical volumes and whatnot manually.
I haven’t explored the full scenario even now. The goal is to have the encrypted Ubuntu partition, and to have the home folder structure on a separate disk drive; encrypted, of course. I’m currently at the point where the entire Ubuntu data partition is on the same drive as Windows 11. I need to create an encrypted partition on another drive and add it into the existing encrypted file structure as /home.
More fun!
