Cloud & Privacy: Boxcryptor

Abandon privacy all ye who enter the cloud” is something that should be engraved over the entrance of most, if not all, cloud services.

At least this is what it feels like to me, having to relinquish all notion of privacy and intimacy knowing my files will be analysed—some cloud providers being more invasive than other in that regard. 

I’ll gladly open all my files and folders to any legit authority asking me to do so, provided they have a reason and the right to ask. But I don’t want anyone else accessing my files–be it on purpose, in order to offer me some service, or because of a security breach–to be able to read them.

I don’t want anyone to discover that I’m the author hiding behind the pen name of dear « Dulcinea Von Liebe, Duchess of Hot Steamy Romance ». I don’t want anyone or any algorithm to be able to read my medical documents, or to see the pictures of my cat. That’s none of their business. That’s, you know private. And that’s not the reason why I decided to use cloud to store my files.

The obvious solution would be to not use the cloud at all. Problem solved, thx for reading, bye. Save that I want to use the cloud: it’s a great tool. It’s just the lack of a stricter legislation that makes it such this Wild West and this Eldorado for those companies, giving them free rein over our data.

Enters Boxcryptor. 


In a nutshell, Boxcryptor is a service that will sit between your files, on your computer, and your cloud provider–they claim to work with most if not all cloud services–and they will encrypt your files before syncing them with your cloud.

It’s available for Mac, Windows, iOS and Android.

What’s great with Boxcryptor is that it’s invisible. Once installed, you can keep using whatever cloud you fancy and access your files like you’d normally do. Beside an occasional speed hit, you won’t notice any change.

Remember the first screenshot in this article? Here is what the same files would normally look like when accessed through Boxcryptor:

The only noticeable change in your workflow is that you must always access your files through Boxcryptor’s virtual drive, not directly from the cloud app itself. Why? Because if you don’t, you’ll access your encrypted files–see first screenshot–and you won’t be able to do much with those.

On a Mac it means that instead of opening the Finder in OneDrive->My Folder->My File, I now open it in Boxcryptor->OneDrive->My Folder->My File.

As you can see, it’s a tiny change. For the rest, you’ll be able to open, edit, share, copy, delete all your files and so on, as long as you remember to access them from Boxcryptor and not from your cloud directly.

Is it really secure?

I’m no expert, but they use strong encryption and, unlike all cloud service providers, they don’t own your private key: only you have it.

Technically, as far as I can understand, what you are the only one to own is the password used to connect (once) to your Boxcryptor account, not the key itself. But don’t quote me on that. The thing is that without this password, no one can read your files–so, do not loose it, there is no recovery.

Can the NSA bypass it? No idea, but for me it’s more about keeping private companies at large than fighting the NSA (hi, guys).

No cons?


I already mentioned the occasional speed hit. For no apparent reason the Finder, as the File Explorer on Windows, will sometime slow down. I can live with that.

Boxcryptor being some kind of virtual drive on your computer, doesn’t always play nice with other apps but nothing dramatic either, just occasional hiccups.

Some apps & services don’t like that privacy layer. Using Boxcryptor you’ll loose access to some options, like say automated versioning and auto-save in Microsoft Office 365/OneDrive. So, use the free version of Boxcryptor to check you can still access everything you need, before committing.

Always check every file has completely been synced before reopening it. I learned it the hard way with Calibre’s metadata and library, as I store my ebook library in the cloud–which is strongly advised not to do so it’s neither Calibre’s or Boxcryptor’s fault here.

Help could be better: simpler and more detailed. That said, coupled with their support forum you should find all you need to know.

There is an iOS version too, which is great, but its UI is lacklustre.

The initial setup can be tricky. I mean, it’s simple but it still is geeky and many options make little sense if you don’t take time to read the online help.
Here are the key steps you must follow to avoid any surprise:

  1. Check you’ve already configured and synced all the cloud services you want to use on your computer: Boxcryptor comes in a free tier (allowing one cloud only, and sync up to two devices) and a paid one (as many cloud and devices as you want, and a few other benefits).
  2. Install Boxcryptor, login.
  3. In its Preferences, check that Boxcryptor has correctly identified your cloud service, then click the link button for each one: Boxcryptor needs to access your cloud files.
  4. Finally, tell Boxcryptor what folder to encrypt. Do not encrypt the root folder of your cloud service, use a dedicated folder, or multiple ones.
  5. It will copy the folder to encrypt (to avoid conflicts with your files on the cloud) and add an «_encrypted » extension to it. Don’t touch it while it’s doing its stuff. When it’s done encrypting, you can remove this extension.
  6. Let it encrypt your files and let your cloud sync all changes back before you start working with your files again. Here again, it will prevent any conflict.
  7. One last suggestion, though: if you use Boxcryptor’s paid version you’ll have the ability to encrypt file names too (not only their content). If you plan to use that option, activate it before you start encrypting any file or folder, otherwise Boxcryptor will have to process them once again, and sync them back to your cloud.
    Go to the Preferences and in the Security tab, check Enable Filename Encryption.

Having to pay for something that should come as a default with any cloud storage? Sure, it’s a pain. Alas, a stricter respect of online privacy is not something I see coming anytime soon: there is too much money involved in mining our data, preferences and habits. And there are so few politicians willing to push legislations forcing companies to respect our privacy. So, unless you have a better solution…

Free or paid version?

The free version works exactly like the paid one, but will only let you use one cloud service (unlimited, with the paid tier) and sync up to two devices (vs unlimited), and you won’t be able to encrypt file names, only their content.

That last bit is an obvious weakness in protecting your privacy, as it’s much harder to just guess what is in a file named “怐濗搎戬晌沝涞汀䀤” than, say “Secret Plan to Conquer the World.docx”.

The paid version is €36/year.

It’s up to you to decide what a better privacy is worth to you. There is no question for me, if only for the peace of mind it gives me to know that even if some hacker could access my cloud storage (s)he won’t be able to read my files that easily.


« Hello Boys! I’m back, » for now

For the last couple weeks, I’ve been writing on my old 2015 MacBook Pro again. No surprise, I enjoyed almost every single moment of it.

Above all I was, you know, happy–the difference was obvious in my work: my daily word count skyrocketed. It felt so good to use some of my favourites apps again. Apps that have no true equivalent on Windows (or they’re not as good):

  • Ulysses. Is this the perfect writing app? Nope. Are there things that drive me nuts in this app? Yup. There will never be such a thing as the perfect app. The right question to ask is « is there any better app available? » I will let you answer this for yourself, as it is a highly subjective matter. 
  • Day One. I’ve been using this app for maybe 7 or 8 years. I immediately felt at home using it, and I still do years later. 
  • The Dictionary, the one that comes with macOS. It’s always overlooked, but it’s such a great app, and so well integrated into the Mac.
  • PDF Expert. Preview, is my go to app for image viewing and is a great PDF viewer. But PDF Expert is so much better. Plus, it comes with an inverted color mode that helps a lot with my poor eyesight.
  • Vellum, for creating epubs and Kindle ebooks. Yeah I know, it’s expensive but there is a good reason some of us consider this app alone worth owning a Mac.
  • Edit: there is also SpamSieve, the best spam filter there is.

All other apps I use regularly have an official Windows version, or there is some alternative.

The Mac and the iPad

The other great thing about the Mac–and about Ulysses and Day One–is the iPad.

Both apps work great on the iPad: their iOS version is as good as the Mac version, while being optimised for touch/tablet use. And the iPad itself, well, it still is my favourite tablet out there, by far. But what do I use it for?

  • Writing longhand (Apple Pencil) for research and drafting (using Microsoft OneNote or Notability),
  • Typing (Ulysses, Day One), with or without an external keyboard,
  • Reading (Books, Kindle, Marvin, the best epub reader out there),
  • Listening to music (Apple music),
  • Watching stuff (Apple TV or whatever its name is),
  • Drawing (Procreate).
  • No gaming, beside a chessboard (Chess Pro and Lichess), as I’d rather use a PC for that.

My iPad is an oldish 9.7 Pro from late 2015/early 2016, but it still works perfectly well as is the Apple Pencil–as soon as you put a matte screen protector over the glossy screen: drastically lowering glares and making the surface feels much more like actual paper.

Not only is it a great ereader–one where I can easily zoom, and take notes–and a great TV/jukebox, but it also is an amazing portable typewriter on which I can work for hours.

That said, I don’t multitask on this iPad. I’d rather use macOS or Windows and have, you know, not one, not two, not even three but as many windows as I want, a fully-fledged Finder/File Explorer, and so on.

Why did you left Apple then?

My old Mac was, and still is, dying, and I need to trust my hardware. At least, I need to know that I can replace the hardware the moment it fails, without any interruption or fiddling around. Alas, I also knew back then I could not purchase a newer MacBook Pro because of their shit–did I just say shit? I meant to say ‘poorly designed’–Butterfly keyboards.

Even more discouraging than Apple incredible failure with this keyboard, was their contempt for customer complaints and their stubbornness in keeping selling this poorly designed keyboard, for way too many years.

Then there was my eyesight problem and the way Apple puts its design obsession so much above anything else that it feels to me like they refuse to make macOS as accessible-friendly than it ought to be–much less accessible than Windows 10 is nowadays, imo.

What has changed for me since then?

  • Thanks to a lot of surgery, my eyesight is better today than it was a year ago–even if my eyesight would still be considered terrible by the majority, it’s incredibly better than it was. Those doctors are magicians. As a result, I’ve much less problem using macOS nowadays than I had a year ago.
  • The recently released 16 inches MacBook pro is giving me hope that Apple has not completely forgotten why we use laptops (not to stare at them in awe, like we could in front of a thin jewel-like but useless marvel) and has not forgotten how to build laptops right–like they used to.

What about tomorrow?

I’m willing to see how it goes with Apple. I hope they will keep on changing all that went wrong.

But I’m also slightly less naive than I was in regards of my dependance on Apple. So, I’ve created a setup that will let me change hardware and OS in a heartbeat, or so.

The only exception here being Ulysses because of its somewhat lacking Export tool (guys, I know you can do much better). So I wrote my own ‘Ulysses to docx’ converter. It’s rough and not suited for anyone but me, but it gives what all the features their own tool lacks–and it gives me peace of mind.