Why It's Hard To Choose A VPN Provider

April 16, 2017

As @SwiftOnSecurity says:

“Just pick a good VPN” is like telling thirsty people to “go to a store and drink clear liquid.” They drank bleach, but at least you helped.

Yup, that pretty much covers it.

The amount of misinformation directed at potential VPN customers is vast. Worse, most prospective customers deeply misunderstand what VPNs do and under what circumstances they’re useful. It should be no surprise that this combustible mix of misinformation and misapprehension leads many astray.


Misinformation about VPNs comes in many forms and is not always easy to spot.

For example, a simple Google search for “best VPNappears to turn up reputable and timely VPN rankings. Alas, the top results are nearly all driven by affiliate marketing; placement in the rankings is entirely dependent on financial performance. It’s hard to imagine that the VPN with the best affiliate payouts is necessarily the most trustworthy and secure service on the market!

For a taste of how distasteful VPN affiliate marketing can be, peruse Google’s results for “VPN affiliate programs”. Here’s the current top hit; it gets worse from there:

If economic incentives are stacked against VPN consumers, so too it seems are the words of the providers themselves. The recent repeal of FCC privacy regulations led to a bonanza of new VPN customers and new VPN marketing efforts. Many providers conveniently forgot to mention important details about the repeal, including the fact that the privacy regulations in question had never gone into effect. If you didn’t feel the need to protect yourself from your ISP yesterday, perhaps you shouldn’t feel the need today. Moreover, when you use a VPN from home you’re effectively replacing your ISP with your VPN. Alas, the policies and behavior of VPN providers as a class is typically far less scrutinized than that of the largest ISPs. Is the tradeoff a clear win?

Publications with specific agendas also have a part to play in misleading customers about when VPNs are useful and what they’re useful for. For instance, TorrentFreak seems to think that third-party VPNs are useful for anonymity; in my opinion, they aren’t. Anonymity is a very strong condition that is hard to achieve in practice. Consider that people with deep technical skillsets and strong incentives to remain anonymous regularly fail to do so. I can’t decide if TorrentFreak’s language about VPNs is a sign of compromised ethics or just wishful thinking; either way, I’m sure it generates clicks.


Consumers interested in VPNs typically have zero experience with threat modeling. A good threat model addresses three questions:

  1. What information am I worried about having exposed?
  2. Who might be able to access that information?
  3. How might they be able access it?

The vast majority of customers can’t answer either of the first two questions with any clarity. Are you concerned about losing your banking password, being tracked by advertisers, or having interlopers learn about the sites you’re visiting? Is your attacker the NSA, your ISP, or people sitting in the same coffee shop? The right answers necessarily alter the strategy and, critically, the tools. (If your adversary is the NSA, no consumer VPN will help you. And if you’re worried about losing your banking password, breathe easy: your bank uses HTTPS everywhere; you don’t need a VPN, even on untrusted networks.)

Beyond this, the question of how an attacker might obtain one’s data requires a grasp of networking and software security that understandably goes far beyond the ken of all but the most sophisticated potential purchasers.

Needless to say, VPN providers take advantage of these fundamental misunderstandings to sell “enhanced privacy”, “true anonymity”, “military-grade encryption”, and other meaningless concepts. Snake oil sells.

Into this swirling chaos arrive the knights in shining armor, striving to shed light on a murky situation. Amongst them is That One Privacy Site (TOPS), which seems to have seen a massive spike in traffic after the United States’ ISP regulation repeal.

I have every reason to believe that the intentions of the TOPS website are good. Alas, even the white knights end up mostly leading consumers astray. TOPS attempts to provide objective metrics by which VPN providers can be judged. Information about providers is broken into categories like logging, data leaks, jurisdiction, etc. For truly savvy consumers, I suspect TOPS is extremely useful. For everyone else, I suspect it simply makes them miss the forest for the trees. Naive consumers visiting TOPS do the obvious thing: look for the VPN with the most green boxes and conclude that it’s the one to buy. The problem with this approach, as @KennWhite of the Open Crypto Audit project expressed to me:

Unlike trying to technically evaluate, say, IPSec vs OpenVPN which have fairly well-characterized objective security properties, assessing the security guarantees of a VPN service is less straightforward, and it basically comes down to trust signaling.

That strikes me as exactly right. When you use a VPN, you’re sending all of your data — presumably including unencrypted data — through your provider. No technical guarantees exist to ensure that your provider will be a trustworthy steward of this information. Instead, one must look at qualitative measures to evaluate a VPN; none of these are addressed by TOPS:

Questionable/sketchy product marketing & SEO, transparency of technical architecture decisions & assurances, openness to independent 3rd party review, ethical business practices, and — crucially — existence of an actual sustainable business model; these are all factors in evaluating the security posture.

Even along axes measured by TOPS, confusion can reign. For instance, privacy policies vary greatly amongst VPN providers. Plenty of reputable providers perform some kind of minimal time-limited logging both to help with customer support and to ensure that their network is responsive to abuse complaints. It’s absolutely possible for providers to both log data and provide meaningful security guarantees to customers. On the TOPS site, a “red” box in the policies or logging columns might genuinely be a red flag, or it might instead be the sign of a subtle and thoughtful provider.

Another axis that TOPS attempts to “measure” objectively is jurisdiction. With red boxes aplenty, naive consumers are quickly led to believe that VPN companies based in the United States or other Five Eyes countries are somehow worse on privacy matters. This conclusion is trivially wrong, of course. A VPN company based outside of Five Eyes can easily have a rotten privacy policy. Worse, they can simply fail to uphold the policy, silently abusing their customers’ trust. On the other hand, a VPN provider based in the United States is beholden to strict consumer protection laws and the potential scrutiny of agencies like the Federal Trade Commission. Policy documents should be legally binding; a good provider will have a government that enforces them.

Finally: TOPS is sometimes completely wrong. The TOPS maintainers have to keep a lot of information up-to-date so I don’t fault them for this. Nevertheless, the inaccuracies I’m aware of do make me suspicious of TOPS’ overall reliability. For example, TOPS claims that Cloak’s native apps leak IPv6 and DNS traffic. Neither is true. We’ve actually prevented leaks on dual-stack networks since our earliest alpha builds; we suspect this puts us ahead of the curve on such a fundamental security issue.

Trust signaling

In sum: it’s hard to choose a VPN wisely. For many potential customers, I worry it’s impossible.

Over time, I’ve developed a framework of six trust signals that I look for when I evaluate competing providers. I hope these will prove helpful in choosing your VPN provider:

  1. Do they have a clear and sensible threat model? (See Cloak’s; for more color, read my thoughts on security, privacy, and anonymity.)
  2. Do they have clear and unambiguous corporate ownership? (Cloak seems unique in offering actual pictures of our actual faces.)
  3. Do they have clear and unambiguous privacy policies? (See Cloak’s.)
  4. Do they have a demonstrable track record of security-mindedness and responsiveness? (See Cloak’s response to Heartbleed and to the “Looking Glass” paper.)
  5. Have they undergone a technical audit? (Cloak has and will again.)
  6. Do they charge money? (Free VPNs are usually the shadiest of the bunch, in my experience.)

It’s rarely easy to answer these questions! In my book, the VPN providers that make it easy to do so stand at the top of the heap.

Every once in a while, I think about starting “That Other One Privacy Site” to address these six broader concerns. Then I remember that I’m likely to simply become another pseudo white knight, contributing more to the noise than to the signal.


January 20, 2017

Today, as Donald Trump takes the oath of office, America is diminished.

And yet, I have hope.

After the election, I worried that protest would be meek and partisan. It has been neither. Voices across the political spectrum have risen in dissent. I’ve been particularly heartened to find many thoughtful conservatives who understand exactly what Trump represents, and who will give no inch when none can be given. John Kasich, John McCain, David Frum, Evan McMullin, Mindy Finn, Susan Hennessey, Eliot Cohen, and Rick Wilson have all spoken clearly, and unequivocally, about Trump’s perilous potential. These are Americans with whom, in sunnier times, I might entirely disagree. But such disagreements live within normal political boundaries. Trump operates far outside those boundaries; we must realign in response.

From Eliot Cohen’s savage and sobering Truth in the Age of Trump:

Trump lies because it is in his nature to lie. One suspects that there is nothing inside this man that quivers, however slightly, at an untruth. It is not uncommon for politicians, to a greater extent than most people, to believe what they want to believe, or to change their take on reality depending on what is convenient for them. With Trump, however, this will to believe is pathological: his psyche is so completely besotted by Trump that there is no room for anything, or anybody else.

I hope to one day revisit what I’ve written about Trump and laugh at how hilariously wrong I was. I hope, but I fear that day may never come.

Political Priority Alarms

January 6, 2017

Of all the political issues I might be worried about, why am I so concerned about trust and nuclear weapons?

Given Trump’s terrifying statements about nukes, I think the fear should be obvious. I don’t worry for the children of Seattle; I absolutely do worry for the children of cities across Asia, particularly within range of North Korea. Do I think Trump would actually do something so nightmarish as to start a war there? No, not with high probability… but not with zero probability, either. The truth is, I genuinely have no idea. Does anyone?

Trust strikes me as the far more insidious concern. Trust may have been eroding before Trump, but he willfully accelerated the process. I have no doubt that he will continue to sow distrust in our government and media institutions throughout his tenure. This is a poison that will linger, harming our country long after Trump is gone.

A friend asked me whether these should truly be my top two concerns. After all, we should probably be alarmed by Trump’s autocratic tendencies, his malicious xenophobia, and the apparent conflicts of interest that could lead us to kleptocracy or worse. To all of these I say yes, I’m worried, but I also think we can muddle through this sort of madness. One doesn’t muddle through a nuke, however, and depending on how far one travels, one may never quite return from the dangerous road of distrust.


November 10, 2016 :: musings

The trouble with black swans is that, even when we know we’re looking at them, it’s hard to foresee their consequences.

Trump is undoubtedly unique in the history of the American political experience. To attempt to parse his victory, or to shoehorn our expectations for his presidency, within the confines of politics-as-usual is to fail to see what’s right in front of us. Trump lives far outside the political norm; why should we expect his presidency to live within it? I don’t believe the republic is likely to collapse, but it strikes me as dangerous to assert that everything will be okay.

President-elect Trump arrives at the White House on the winds of alarming political, economic, and racial unrest. There can be no argument that he channeled our lesser instincts — those of the bully, the bigot, the racist, the anti-factual, the petty authoritarian — into an effective political weapon. This is unforgivable, but it doesn’t diminish the validity of at least some of the unrest that led half of America to vote for him. I can understand how the economically downtrodden and culturally sidelined might, in some warped way, have felt like a vote for Trump was the only viable path forward.

There’s so much work to do. We need to understand and address the root causes of the unrest that led us here. Perhaps a Trump presidency will give us the opportunity and impetus we need to get started.

But the KKK? The Nazis? They never left us. Now, emboldened by our President-elect’s words and deeds, they’re coming out of the woodwork. On this count, I think Trump is already a tragedy of unimaginable scale.

Inflection Points

May 27, 2016

It’s been a nutty couple months.

Peter, Nick, and I sold Cloak! It turns out selling a company can keep you plenty busy.

The sale was a surprise ending for us. It’s also an exciting new beginning.

We didn’t need to sell; Cloak was happily profitable, and those profits were growing. We didn’t necessarily think we wanted to sell, either, at least at first.

However, as we began to plot out Cloak’s next eighteen months, we realized we were at an inflection point. Our investments in engineering automation had allowed us to run lean almost to a point of absurdity. But our leanest days were clearly numbered.

It didn’t take long to realize that we couldn’t take the next steps without growing our team. We needed to ship native apps for Android and Windows. We had to move aggressively to better serve our growing list of corporate customers. We wanted to scale our VPN network. We hoped to make our apps behave more gracefully even in the face of less common network failures.

All told, it was clear that Cloak in mid-2017 was going to look quite different than Cloak in early 2016. We assumed we would lead that charge… until a few potential suitors knocked on our door. The question then became: would we lead the charge? Or would we team up with a larger organization to make the next big push?

In StackPath we found an ideal suitor. Their plans nicely complemented and strengthened our own. They had a deep bench of business, sales, and marketing talent that we knew we needed. And it didn’t hurt that StackPath understood the value of what we’d built, and was willing to pay a fair price.

So here we are! I’m a full-time employee of StackPath. I have a boss. We have a mission. It’s the same as the old mission, only bigger. I’m excited to see what we can build.