Disintegration and Compartmentalization: Necessary Best Practices

Several months ago, I wrote about my never-ending privacy story. Since then, I’ve given numerous presentations about security and personal privacy. In one of those presentations, I talked about how using personal clouds (e.g., Nextcloud) could limit your exposure to those who offer you their “free” services in exchange for your personal data. But there has always been an elephant in the room. Specifically, we want to have a simple and easy desktop experience – myself included. And most people will trade almost anything for that experience. But those carefree times where everything is “free” and everything is “safe” are now disappearing. So to kick my privacy efforts up another notch, I’ve begun the process of online compartmentalization.

As you read that word, many of you might be thinking about the psychological consequences of compartmentalizing your life. And almost every psychologist will tell you that breaking your life down into smaller fragments separated by impenetrable walls can be unhealthy. These self-imposed walls separate your family life from your work life and your faith life. Some people keep all sorts of separate personalities locked up in secure closets. And this can be a terrible burden.

But when it comes to privacy and security, you can no longer afford to keep all of your eggs in one basket. In fact, compartmentalization is now becoming an altogether mandatory part of a “connected” life. You should not let data from your home life be accessible to actors in your work life. And it would be wise to dis-integrate your work life from your home life.

The Technologies of Disintegration

In order to protect the integrity of the various roles in our life, you need to isolate data. But that is increasingly difficult. For example, most businesses ask you to be “on call” twenty-four hours a day, seven days a week. But they don’t want to pay for a separate phone. And they want to ensure that any personal equipment does not exfiltrate company data and/or intellectual property. So most companies reserve the right to access all of your phone’s capabilities (and data) in order to protect any of their data which might be on the phone.

You can easily see the problems with this example. If you are considering alternate employment, it might be unwise to let your current employer have unfettered access your email and instant messages with potential future employers. Fortunately, there are technologies that can help you build the walls that you might want (or need). These include: virtualization, containers, and secure cloud services.

Step One: Use Application Virtualization

We are victims of a culture that shares way too much information. For many of us, we willingly share data with companies that we shouldn’t trust. We do this so that we can share even more personal data with friends who really aren’t our friends.

And we count upon our applications to enable this kind of sharing. We unconsciously (and indiscriminately) copy and paste data between apps. Of course, this allows bad actors to exploit data sharing as a channel for data exfiltration or data corruption.

But if we want to protect ourselves, we need to erect barriers between apps. And the latest means of erecting such barriers is to exploit containers. Whether we use snap or flatpak, we are adding an execution layer that seeks to impose barriers. And the same thing is rue for the other darling of micro-services: Docker. Like the app management tools provided by Linux distro teams, the folks at Docker are trying to standardize application execution and enable application isolation.

Among other activities this summer, I’ve invested quite a bit of personal time into Docker, docker-compose, and a variety of support apps. And I now use Docker for Plex, Let’s Encrypt, most web servers (and proxies), the TICK stack (i.e., Telegraf, InfluxDB, Chronograf, and Kapacitor), and a variety of home automation applications.

Step Two: Use A Secure OS

Nevertheless, sometimes, you need more than just a good application manager. In order to effectively use compartmentalization as a defense, you need to get onto a more secure OS. Most security experts will tell you that there are many platforms that are intrinsically more secure than Windows. Yes, you can harden Windows. I know. I’ve done it for myself and for other. At the same time, you need to use a platform that is not built by someone who makes money off of your identity (e.g., Apple).

Earlier this summer, I finally switched to a Linux-only infrastructure. All of my Windows servers are gone. And all of my Windows desktops are now Linux desktops. I have rooted all of the phones that I can and replaced their OS with one that is no longer dependent upon Google services.

Step Three: Use System Virtualization

While you may run your apps in virtual environments and/or containers, you probably need more compartmentalization. Yes, you should isolate your apps. But you also need to isolate systems from one another. Indeed, there are times when you need more than just a secure app. You need a secure stack.

Over the past few months, I’ve started using virtual machines to isolate applications that are accessible from the Internet. I do this so that I can minimize the damage that can be done from any single app to the OS that it runs upon. By adding system isolation in addition to app isolation, I have increased the security and availability of my customer applications.

Step Four: Use The Most Secure Platform That You Can Afford

All of us can be more secure. But for some of us, the cost of maximum security must be paid – either in coin of the realm or in tokens of inconvenience. For me, my most important resource is my time. So I carefully choose each and every experiment that I undertake. And this past weekend, I finally chose to take the leap – and I finally added Qubes OS 4.0 to my core laptop.

The process of moving to Qubes was frustrating. I had just reclaimed a 500GB external SSD drive. And it took about four (4) hours to get Qubes installed. It’s really not that hard. But special partitioning and formatting was required in order to write to the drive. In the end, I had to write the boot image onto a raw partition on a thumb drive. I then had to update grub on my internal drive so that I could multi-boot. Finally, I re-partitioned the SSD drive and finally wrote Qubes to the external drive. After completing the installation, I can now boot to either my internal Ubuntu 19.04 system or to my Qubes OS 4.0 system.

Step Five: Consciously Choose Your Threshold of Inconvenience

I must now learn how to use my “reasonably secure OS” to perform my day-to-day activities. Last night, I spent a few hours setting up my entertainment / streaming apps. [Note: Yes, they are important. I really do like to listen to music as I write.] And for what it’s worth, I am now writing this post from my Qubes OS system. It took some time to set up NoScript properly. But once I did that, I’ve had little problems with this blog post. And earlier this morning.

Alright, that’s not altogether true. The simple process of sharing files between processes is a tad more complex. For example, when taking a screenshot of the entire desktop, the file is stored in the dom0 (i.e.,master domain) file system. So I had to learn how to copy files to/from dom0. But once I figured that out, I realized that the process isn’t nearly as hard as it had originally seemed.

Takeaways

I’ve finally addressed some structural insecurities in how I use my computers – both at work and at home.

• We moved to a Linux-based system.
• The team migrated to containers both for casual (desktop) apps and for more service-oriented applications.
• Our IT team moved key services onto virtual machines that could be isolated from less disciplined processes.
• Finally, I converted my primary laptop to an even more secure OS (i.e., QubesOS) – one that features compartmentalization and maximum isolation).

Do you need to do all of these things? I won’t answer that for you. But as for myself, I needed to become more secure. So I took those steps that I needed to take in order to become safer and to secure my private life from public scrutiny.