A client called us in a panic. A third-party Dropbox plugin they relied on to encrypt sensitive documents was being discontinued — and they had one month to figure out what to do. The plugin handled everything that couldn't be exposed — client passwords, API keys and secrets, private contact information.

We started where we always start — with questions about the organization itself. How did people work? Where did information live? What tools did everyone actually use every day?

That last question is where the conversation changed. Almost everyone used Obsidian — a markdown-based note-taking tool that was the connective tissue of the organization. Two things caught our attention: its ubiquity meant adoption wouldn't be a training problem, and its architecture — plain text markdown files with a rich ecosystem of community extensions — meant we could build directly inside it.

We developed an encryption framework built around Obsidian's native structure. A custom extension handled encryption and decryption invisibly. The migration of existing data became a handful of scripts the agency's one-person IT team could run to automate the conversion. What might have taken weeks took days.

Then came a request we hadn't anticipated. Some managers wanted sensitive information on their Trello boards without it sitting exposed in plain text. The framework handled it — we built a Trello power-up that drew on the same encryption system. A need that emerged after the solution was built found a home because the solution had been designed as a framework rather than a fixed system.

What the agency came to us with was a crisis. What they left with was something more durable than what they'd had before — an encryption system they owned entirely, built around tools their team already trusted, with no third-party dependency that could be discontinued without warning.

The one-month deadline turned out to be enough time. Not because we moved fast. Because we spent the first part of it asking the right questions.