Better Personal Data Management

I switched from Ubuntu 22.04 to Debian 11 earlier this year. I was using Ubuntu’s LTS OS versions for nearly 9 years before that, since 2014. The switch to Debian was because I stopped liking what Ubuntu had done with the OS: The GUI has become a strange mix of Ubuntu’s old desktop environment (Unity) and the Gnome Desktop Environment, which is standard and popular. I generally use the i3 window manager, so the Desktop environment was not too annoying; I could have lived with it if not for Snaps. The introduction and use of Snaps was a continuous thorn in my setup. Each snap sets up a new loop file.1 So, the output of df is polluted with these strange loop devices that I don’t care about. Also, Firefox installed using Snaps does not work well with the KeepassXC Browser integration. So, the recommended way for installing programs on Ubuntu was actively getting in my way. (There is also some Ubuntu bloatware but an equivalent of that is there in almost every other non-base distribution, so it can’t really be counted against any single distribution.) I wanted to do a few things differently with this reinstall.

Frequent OS Version Updates

Over 9 years of using Ubuntu, I used only 3 LTS versions. I was hoping that I would not have to go through the OS installation process multiple times, which would save me a bunch of time to learn and set it up properly each time. But this approach was wrong. Every time that I thought I would not have to install the OS again for at least 5 years, my plans were thwarted and I had to install the OS within 3 years or less. This was due to first, a new laptop, then a crashed HDD, then a new laptop, then a glass of water spilled on my (spill-proof) laptop keyboard, and finally, another new laptop (a cheap replacement for the one that I ruined.).2 So, now my target is to update to the latest version of the OS every year. Of course, it comes with recent Linux Kernel versions, but also ensures that I am on the latest version of most packages. (I had a lot of problems running Ubuntu 16.04 LTS on my old laptop, barely 1 year after its end of life, because a lot of the packages that I needed were not being packaged for that version of the OS at all. So, I had to manually build a lot of things. And each of those things had its own dependencies, which were also not packaged for older versions of the OS, … and so on.) Also, the increased speed that comes from running the latest software on a very old device is stunning. After upgrading from Ubuntu 16.04 (released 2016) to Ubuntu 22.04 (released 2022) on a 9 year old i5 Dell Inspiron machine, the computer became usable. It was totally fine for the normal mix of writing / reading / Netflix / YouTube. The laptop has a hard drive, which I suspect caused the fans to spin up when I was streaming video, but everything else worked well.

Decouple Data from the OS

Regrettably, until a few days ago, I was blasé about managing my data properly. There were a bunch of folders, with a lot of files, and they were all sort of required, but I never really knew which external hard drive to check for what files. Backups were not regular or complete. I used Dropbox for some use-cases, but not for others (which doesn’t make much sense.) It isn’t like this approach had not already caused me problems: I have accidentally deleted and (through a painful process) recovered a folder containing all my files from college twice, and both times because I was trying to get all this data under control, but I was doing it with the incorrect rsync command. On my computer, I was used to putting all my files inside the home directory. There were a few files scattered around in ~/code and ~/personal. It was really an unmoderated (and embarrassing) shit show. Linux provides the elegant concept of partitions. The /boot partition consists of your kernel and things that should be kept in plaintext, the / (root) partition consists your OS files and /etc, /var etc: These should be the things required to login. Finally, there is the /home partition which consists of things that you would use only after logging in: SSH and GPG keys, configurations for your software, your shell configuration, personal files, etc. You should be able to reinstall your OS by changing just the /boot and the / (root) partitions. The /home partition can be left untouched by a new OS installation, and should work seamlessly with the next version of the OS. I am going to better implement data management by using various partitions, and ensuring that all of them are encrypted properly.


As I mentioned above, every time I thought my computer was basically indestructible (why did I think this?) and that I will not run into a situation where I would have to give it to someone else unlocked, I had to give it someone unlocked. The technicians who service your laptop will undoubtedly ask for the password of a user on the system. This is unavoidable.

The correct way (if there is one?) would be to have a “Support” account with a documented password on all your computers, and keep it free of any personal files and ensure that if you have to hand your PC to someone else and let them connect to WiFi or inspect the PC’s configuration, they can do so without having access to your files. Even this might not be good enough, because some times they might want to do things which require the administrator’s password, and the administrator password often gives them access to your files as well.

The only way to really get around this is to keep the files required to start your computer separate from your personal stuff. Once again, a separate encrypted partition that you manually mount on login seems like the best answer here. The overhead of mounting the partition on each login is tedious, but this can be gotten around by using the TPM or a FIDO device. (Note that if you use your TPM, which is very convenient, then the support technician can technically use the TPM To also mount your devices because the TPM doesn’t check if you are the one who is mounting the device.) Using a FIDO device (YubiKey) is better, but inconvenient because you have to keep the device close to your computer. YubiKey does manufacture low profile FIDO keys which take up one USB port and stay connected to your device, but can be conveniently disconnected before handing the laptop unlocked and over to someone else. That might be a good balance. I am still figuring this out. The trade-off between convenience is security is not a novel debate at all. (The most popular operating system, Windows, gets around it using Bitlocker, which will keep the security key in your TPM and keep a recovery key on Microsoft servers. You can never lose your key and its super convenient, but Microsoft will have a copy of your key.)

Don’t Forget How to Install Operating Systems

This one is controversial and I have had different feelings about it over the past few years. For a while, I loved configuration and tweaking and changing my setup constantly. (The very beginning of my journey with Linux was just installing and uninstalling operating systems on an old Windows desktop machine, crossing my fingers, pressing the power button, and hoping that the computer boots up properly.) Then, for a long time after that (pretty much until the accident with my laptop last year), I craved stability and the same OS version throughout. Now, I am back on the configuration/tweaking part of the cycle, but I don’t want to configure for the sake of configuring. I want to build a configuration which makes it easy to configure in the future.

This is similar to the approach that one would take with an editor like Vim or Emacs: There is a period of intense configuration when you first adopt the editor. But later, things cool down and there is much less to configure and the time spent using the editor far outweighs the time spent configuring it. (One of the efforts with my latest install is that I am using Ansible, a configuration management system that I am familiar with, for doing almost all the installation and building that is required. This is already paying dividends, because I can run this Ansible on a new computer, and get all my software and configuration back. I was surprised at how easy it was to write the initial Ansible configuration, which is the most daunting. The incremental updates to the configuration have been quite easy.)

The thing about installing operating systems on your main computer is that if you don’t know how to do it well enough, you will almost definitely be scared about doing it and keep postponing it. With the limited time that I get, I want to use my computer to do something now; not configure it to do something later. However, there is a point where this logic gets inverted: You keep putting away installing a new operating system. So, you keep forgetting the things you learned to do when you installed an operating system the last time around. Eventually, you end up starting from the beginning and spending way more time installing an operating system than you saved by putting off the installation. I am pretty sure this is the spiral I fell into when I was installing Ubuntu 22.04 after a 4 year hiatus from OS installation on my backup computer last year. The process took nearly 4 days, including all the basic setup, and was quite manual. Compared to that, the Debian installation last month was quick and easy.

Understand the Boot Process

Not knowing what /etc/crypttab and /etc/fstab do, or how to add a new LUKS device, or how to remove a partition from being mounted at start-up, or how to remove the password from one of the LUKS keyslots, etc: These are intricate things that it is not OK to get wrong (because you would not be able to boot properly if you got them wrong.) However, they are also not done frequently enough for you to remember everything. Then, you must rely on your personal notes from the last time you did something (The Zettelkasten system has helped a lot to keep my notes synchronized.) and the learned experience from the last time that you did it. Right now, the past few weeks of configuration updating is fresh in my head. So, I can update the crypttab and fstab file or use the cryptsetup {open,close,luksFormat,luksDump} and the mount / umount commands, without much hesitation. This was not the case when I originally installed Ubuntu 22.04 LTS on my backup laptop or when I installed Debian 11 on my current laptop.

Manage Your Data Yourself

This one might seem like I am fighting the tide of the tide of the “Cloud” here. It is not at all absurd though: You need to build a system, and this takes time and admittedly inconvenient. But once you have it, and start refining it, you can rest easy in the knowledge that your data stays quite close to you and will never cost you more money because the company providing the Cloud decided it was a good time to increase prices.

Take photos for example. They are quite important. When I first set about arranging my photo library early last year, I found that I had taken a lot of photos using various phones that were still stuck on those phones. I had never thought about moving everything over to some central place before, so photos from 2018 were in the phone I used then. Photos from 2019 were in the iPhone I am currently using without any backup. (I don’t use iCloud Photos, so they were stored in just one place.) I know of people who lost a lot of their photos because their phone just refused to start up one day. The helplessness and regret that follows losing important data is neither worth the effort required to build a system to manage data yourselves, nor is it worth saving the money you would pay Google Photos or iCloud, if you are not interested in building your own system. Let’s go back to the start: photos.

Do you take photos with your phone? If yes, do you back up these photos? I have found that there are two answers to this question: The first one is “Yes, I use {iCloud/Google Photos/Dropbox} to backup my photos.” The second one is “No, I don’t backup my photos. Why do I need to? What is going to happen to my phone anyway?” I have found that something always happens.3 When something does happen, but is fixable, you go to the support center. And the first thing that the support person is going to ask you to do is unlock the phone and hand it over to them. This happened both when I gave my Nexus 5X for its motherboard to be replaced and when I went to an Apple Store to get an iPhone’s broken display changed.4 There might be the option to not give them your password, and instead ask the support people to just format everything on your phone. You can’t do this if you have photos on the phone that you want to recover. The good faith assumptions about support people not looking at your personal data notwithstanding, do you really want to hand over your unlocked phone with several years worth of personal digital data about you, your friends, and your family to someone else? I don’t.

So, I use Shotwell to store and manage my photo library.5 This applies to other parts of your digital life as well: Passwords, scanned data (documents like your passport), email. Taming the data that is created as during my life is worthy of its own blog post. I will probably do at least one about email and photos, because those two have been the most interesting exercise for me. During these, I have run into the strange patterns that keep repeating in managing data, the amazing ability that comes about from thinking of everything as a file, the use of GNU tools like comm, sha256sum, awk, sed, and much more.

So, there it is. My rationale for switching from Ubuntu to Debian, and my rationale for frequently updating your operating system through a controlled process, forcing you to automate as much of the setup as possible. The tools are there and all of them are well-integrated into the Debian and Debian-based distributions.6 All you have to do is build your own system.

  1. Loop files are setup using losetup, and allow you to treat a simple file on your filesystem as a block device and do things with it that you would generally only do with a hard drive (which is seen as a block device.) So, you could set up a LUKS container inside a simple file, by setting it up as a loop file, creating a LUKS container on it, then creating a partition table inside it and multiple partitions inside that partition. All of this works because Linux is super strict with abstraction. For me, loop files, and their implementation in Linux, is sort of the pinnacle of great software design. The manual page for losetup, the command used to set up loop files, is informative and easy to read. Something like Tomb is possible only because of loop files. It is not supported on Mac OS because … well, of course anything useful would never exist on Mac OS. (I am forced to use a Macbook at work because of better Mobile Device Management support for that operating system, and MDM is a prerequisite for most IT teams: it allows them to control the company’s data and wipe the hard disk remotely if something happens to the laptop.) 

  2. This happened in September 2022, and it was a soul crushing incident. It overtook my previous “I ruined my electronic device and I can blame only myself” incident from 3 years ago. 

  3. If nothing has happened to you, that’s great. But it doesn’t hurt to be prepared, and that’s what I am evangelizing here. 

  4. Now, I have no idea why this is required: Surely, changing the display has nothing to do with the software itself. But I have no idea how these devices work either, so I am not going to second guess the professionals. 

  5. The process is convoluted, but definitely worth it. I copy HEIC files from iPhone to Windows through the Windows Photos app; then convert them from HEIC to JPEG using CopyTrans HEIC; and then, import them into Shotwell. Transferring photos from a digital camera into Shotwell is extremely simple: Connect the camera to your computer, open Shotwell, and click “Import All.” 

  6. I did not use the cryptsetup CLI tool once when setting up encrypted partitions because the Disks utility on Debian (gnome-disks) works well with LUKS1.