In my ongoing effort to lock down my cyber-life, I jettisoned Dropbox three weeks ago, and I’m quite happy I did.

But I’m not done with the reconfiguration. So, if you have the patience and credulity, you may listen in while an amateur deliberates about the choices…

People more expert about this stuff than I am: please review my various claims here for accuracy. I must thank a gentleman who gave excellent feedback and corrections on my VPN post from a month ago.

Why Resilio Sync isn’t working out for me

As I explained in an update, the solution I went with—Resilio Sync plus backup to an external drive—had some drawbacks that were unexpectedly annoying. Foremost among these is the fact that Sync isn’t a “set it and forget it” technology, i.e., you have to think about and maintain the state of your syncitude, since your devices have to be on at the same time (and Sync has to be working on both/all of them). Also annoying is having to rely heavily on traditional backup, because if God forbid you should delete something inadvertently, your deletion will propagate among your devices (if they’re all on at the same time—entirely possible). I’ve had to use Dropbox’s “restore” feature before; I figure it’s only so long before I have to restore something from my backup, and what happens if my backup program’s restore feature is screwed up or very hard to use? Oy.

These problems are annoying, but not horrible. However, I definitively decided that I had made the wrong choice when I discovered that Sync has no easy way (that I can find) to support the syncing of contacts, passwords, calendars, bookmarks, and text editor settings. Sure, you can sync a data file, but insofar as this same data file (i.e., identical copies of it) must interact correctly with software on each of your systems, then unless the software is specially and carefully written to work with an independent datafile that works the same on all your systems (I think Sublime Text is OK here), you should let your local copy of the software update its own copy of its datafile. This is one of those technical issues that sounds very abstruse, but which poses very real, concrete problems when the rubber meets the road.

The problem, essentially, is that you need to let your software (browser, password manager, calendar, or text editor) handle its own syncing via the cloud. There are two ways in which software can do this for you: (1) you use a cloud you pay for, like Dropbox (e.g., Enpass supports Dropbox syncing), or (2) you use the software vendor’s cloud/server, as email syncs via IMAP with your mail host, which you must trust, or as Chrome and Firefox do with bookmarks, and as Apple does with your contacts and calendar. Boo! Hiss! I’d rather handle this myself and avoid the privacy/security risks, if I can.

Your very own cloud server: a NAS

Well…having decided I’m going back to the drawing board on a cloud/device syncing solution, I recalled that NAS devices solve this general problem very neatly. NAS means “network-attached storage,” and it means basically your very own personal cloud server. It’s an actual box that lives in your home or office, but it’s also on the Internet, so you can access it from anywhere. It’s not a traditional desktop computer; it’s a server. With a NAS, when you sync your devices, they don’t all have to be on, because they sync via the NAS, which is always on (but don’t worry, it doesn’t use much energy). If you ever have to restore your files, the NAS makes it easy without the trouble or worry of having to interact with fiddly backup software. In other words, “file restoration” is built in to the NAS’s syncing software—an “undo” button for inadvertent deletion.

NASes (especially the Synology brand) come with a whole raft of software for syncing particular types of data that work with different apps, like calendars (oh joy! Finally, a plausible replacement for Gcal!), address books, passwords (using WebDAV), and more. This is a decided advantage over Resilio Sync, which simply doesn’t offer such solutions.

NAS devices also support cloud-based collaborative document editing—basically, they replace Google Docs. It’s insane what a NAS can do for you: not just syncing documents and data, not just collaborative document editing, but also (these are all available Synology packages/apps)

  • calendar (replaces Gcal and Apple calendar via iCloud)
  • contacts/address book (CardDav; replaces various)
  • chat (replaces Facebook Messenger, Slack, and Telegram; includes end-to-end encryption)
  • your own frickin’ mail server if you’re brave enough
  • photo sharing (replaces Instagram, Facebook, or whatever you use to share pictures with your family and friends)
  • Discourse (host your own web forum)
  • Apache and support for various programming languages like Java, Node.js, PHP, Ruby, as well as databases; i.e., make your NAS an actual, fully-functional web server
  • Redmine (project management and ticketing system; replaces Zendesk, Pivotal Tracker, Jira, Trello, Asana)
  • multiple options for blog, CMS, and wiki systems
  • video hosting and podcasting
  • VPN (i.e., turn your NAS into a VPN node)
  • Git and Git Server (put your code on your own Git server instead of using Github or Gitlab; handy if you have totally private projects)
  • built-in backup for the NAS

In short, just think of all the computing functions you farm out to the Internet just because you want something “always available from anywhere using a brower.” Well, pretty much all of those services can be had via your own NAS, and a sizeable company (Synology) supports the software.

Now, I’m not saying these apps are as good as the ones available to you from the professionals. Your NAS is not likely to be as fast or as reliable as your current web host. But (a) it’s yours, and (b) you don’t have to worry about the prying eyes of corporate workers, or about hackers attacking the big corporate data honeypots (they might take a crack at your NAS if they think its defenses are poor, though).

Wait, what about zero-knowledge cloud services?

Oh, you thought I had forgotten about zero-knowledge cloud services, like Sync.com, Spider Oak, Pcloud (my son threatened to use this one himself because he didn’t like Resilio Sync), and others?

I started out thinking these were good options, but in retrospect I see they don’t hold a candle to NASes. They specialize in being always-on, reliable, and secure cloud sync/backup options. And that’s good. The problem, however, is that there are an awful lot of cloud services we rely on that put you and your data in the same boat as Dropbox. And even if you don’t need to host your own website or your own mail server, which is admittedly going a bit far, there are very sound reasons at least to want to host your own contacts, passwords, calendar, and so on.

I looked at the features offered by Sync.com, Spider Oak, and Pcloud, and while they seem to nail the traditional Dropbox feature set (which is good!), they don’t support the other cloud features I’m anxious to have. One of the next items on my lock-down “to do” list is to finally replace Gcal and Apple Contacts, and to delete my calendar and contacts from Google. I just hate the idea of leaving these problems unsolved. My ambition is to completely divorce my data and habits from Google, Apple, and Microsoft products. I don’t see how I can do that without either trusting somebody else, or running my own server. Since zero-knowledge cloud services are so underdeveloped at present—and if I were an investor, I’d put money into that, as it strikes me as a potentially huge growth industry—the only option left is a NAS.

Some final reasonable considerations

Let’s take a step back and get reasonable, now.

What is the main concern motivating these deliberations? Not just concern about privacy, but a refusal to entrust sensitive information to corporations that are, essentially, black boxes to me. But maybe I can just accept some risk here. Isn’t that reasonable?

Well, I wouldn’t be where I am if I was prepared to answer “yes. ” My sense of the thing is that having massive amounts of valuable data sitting right in their servers ends up being too much of a temptation to a lot of companies, and they can craft and interpret their privacy policies in a clever enough way to escape much legal risk. And even if I could trust their privacy practices, the many and growing number of security breaches means my data isn’t safe.

I also don’t like the direction that both government surveillance and authoritarian, paternalistic corporate cultures are moving in; while I don’t expect the secret police to bust down the door anytime soon, or the remaining Big Tech companies I have relationships with to cut me off, it’s a definite plus to cut ties with these institutions which have become so corrupt.

I admit my motivations are partly (perhaps only a small part) political. I’d like to lead a revitalized, individualistic civil society in a better direction, help support the ecosystem of privacy-respecting companies, and poke snoops, spooks, hackers, and authoritarians in the eye.

All that said, I don’t expect others to think about this the way I do. We all have our paths to walk.

As for myself, I’ve concluded I will get a NAS after all. Wish me luck with the installation and configuration!