We’ve been providing Cloak customer support for a couple years now. We know Cloak’s most problematic pitfalls like the back of our hands.

There’s one remarkably common confusion that I feel is very telling. It usually starts with an innocent request for help:

What’s my four-digit passcode? I never got one from Cloak.

Cloak doesn’t hand out passcodes, of course. Instead, on iDevices, it installs a VPN configuration profile. As part of this process, users must re-enter their lock-screen PIN.

For most users, installing profiles is terra incognita. There are several steps, comprising several poorly worded dialogs. This is unfortunate, but not necessarily a road block. Many users immediately ascertain from visual cues that they’re being asked for the passcode they always use to unlock their device. A few taps later and they’re on their merry way.

However, a surprising fraction of users simply don’t make the connection. Often, even after we reply, customers tell us that they “still don’t know the right passcode.” No amount of word-smithing to our default reply has yet reduced our initial rate of failure.

I know several people who teach math at the high school and collegiate levels. One common refrain I hear is that students often bucket into two groups: those that identify general concepts, and those that learn recipes to solve specific problems. Both are valid learning strategies, but they can lead to quite different outcomes.

This may be a leap, but it feels like Cloak’s passcode confusion is much the same. One the one hand, some customers have a general notion that they have a passcode, and that this passcode protects their device. On the other, customers have a specific notion that when their device wakes up from sleep, they need to enter a specific code. Installing a configuration profile is far from waking up from sleep; there’s no recipe for how to proceed.

I’d love to hear further examples of this kind of customer support conundrum in the wild.