Encrypting All the Things

Four years ago — four?! — I tried to take back our digital content. How did it go, what has changed since, and what are we doing now?

Not Self-Hosting

Initially, setting an ownCloud instance was quick enough, and good fun. However, as the data inevitably grew, performance became a problem, and I did not have the time to research solutions, such as software upgrades and server hosting alternatives. It is already difficult enough to try and ensure that all the random data you have from all the various sources — documents, photos from phones and cameras, email attachments, etc. — are backed up at all, that worrying about the backup solution itself was not tenable for us. It is interesting to see that Nextcloud have since forked from ownCloud, and I do genuinely wish them luck with an extremely challenging problem.

Evaluating Carefully

If our data is to be entrusted to cloud services, how can we ensure that they are indeed trustworthy? Read around, understand the differences compared to "free" services, and try before you buy (more on that later) on all the platforms that you and your family use. For example:

• Edward Snowden recommends Spider Oak over Dropbox, but Tresorit seem an even better alternative.
• Proton Mail is feature-rich and polished, but multiple users on a single custom domain are very expensive in comparison to Tutanota. Due to their encryption techniques, mail is only viewed through their website and apps, and is not available in an application such as Outlook.
• Dashlane apparently have no knowledge of your encryption key for your website credentials, but do not offer a Linux app like Enpass, and bill annually, rather than once per mobile device.

Try DuckDuckGo and their excellent blog series for great advice on how to stay safe online, and what services you can use to do so.

Browsing with VPN

Consider your browsing habits and history; they are extremely valuable data points! For example, if you have ever wondered why adverts seem so tailored to your tastes, watch how Facebook identify and track you around the internet.

Fortunately, a VPN can help to prevent you being identified. There are plenty of excellent services, such as NordVPN, which provide setup instructions for a vast array of platforms, and a user interface for some desktop and mobile operating systems. This may interfere with some of your standard internet usage patterns: I cannot update Android or Chocolatey apps over VPN in the UK, and occasionally need to forcibly reconnect the VPN when it drops out. However, not only have I seen ads either completely blocked or no longer targeted — the difference between a VPN and standard connection is frightening! — but the ability to connect to a node within another country and watch content that has otherwise been limited, such as some YouTube videos, is pretty awesome.

Let's take a look at a random Buzzfeed article:

Seems innocuous enough? Except... wait, wasn't I revisiting a classic Cillit Bang YouTube remix clip recently?! Let's try that again over VPN:

This time, the ad has been completely blocked by my VPN provider, so it doesn't even reach the browser for Privacy Badger to hide!

Paying!

You get what you pay for, and free is very unlikely to give you the peace of mind you want. Don't forget that paid services generally include better support: I fielded problems to almost every vendor mentioned in this post, and was incredibly impressed with the response of each. Regardless of the extra security afforded, each product has provided me with a feature that has enhanced my digital life, without the overhead of maintaining one or more solutions myself.

In summary: your digital life is never likely to ever be entirely private and secure, but by taking a few steps over the course of several months, and with a little monthly outlay, you can provide yourself with a suite of tools that secure and genuinely enhance your digital life.