Product Strategy

The "Wunderlist Upgrade": Designing a sunset

We didn't just "shut down" Wunderlist. We launched the "Wunderlist Upgrade".

The distinction matters. A shutdown is a loss; an upgrade is an offer. We knew that to move millions of users to Microsoft To Do, we couldn't just force them. We had to entice them.

My role was to design this holistic transition, ensuring that the move felt less like an eviction and more like a promotion.

The psychology of migration

Users don't care about your roadmap. They care about their data.

We weren't just asking them to switch apps, we were asking them to move their "second brain". The risk of data loss (real or perceived) was the primary blocker to adoption.

We realized that success wouldn't be measured by feature parity, but by the sensation of continuity.

The tension

We framed it as the "Wunderlist Upgrade" because we needed to signal continuity. But internally, we knew the risk.

Users don't upgrade unless they see value. And for many, Wunderlist was already perfect. The challenge was to prove that Microsoft To Do wasn't just a replacement, but the rightful successor.

We had to sell the future without disrespecting the past.

Defining the problem

We defined the core problem: Trust is fragile.

If the migration failed once, or if the data looked slightly wrong, users would churn immediately. There was no second chance.

Research

We mapped the emotional journey of a sunset. Denial, anger, bargaining. We saw it all in our research.

We found that "functionality" wasn't enough. Users needed emotional reassurance. They needed to see their familiar list groups, their background images, their specific organization methods reflecting back at them in the new tool.

Designing for continuity

We decided to clone the mental model, not just the data. When the importer ran, it didn't just dump tasks into a list.

It recreated the folder structure, the visual hierarchy, and even the theme settings. The goal was to minimize cognitive load: if it looks like home, it feels like home.

The importer as a product

The importer became our most critical feature. We treated it like a flagship product.

It had to be one tap. CSV exports were tertiary, if even… Just "Import".

We engineered it to handle edge cases, like massive accounts, broken formats, or legacy data.

We added a detailed summary report at the end. Not for debugging, but for reassurance. Explicitly showing "12 folders, 405 lists, 3400 tasks imported" gave users the confidence to finally be at peace to delete Wunderlist.

Trust as a metric

The feedback shifted from anger to relief. People weren't thanking us for the app; they were thanking us for not breaking their workflow.

This reinforced a key lesson: Productivity tools are emotional infrastructure. When you change the tool, you respect user data first. To them it's not data, it's years of tracking tasks for school, work, planning their wedding, preparing for welcoming their first-born child, or important links they saved.

Closing

When we shut down the servers, millions of users continued their day in To Do without missing a beat.

Strategy isn't always about growth. Sometimes it's about ensuring that a community survives the end of a product lifecycle, which is a very tough design challenge in itself.