Virtually Attend FOSDEM 2026

Adversarial Interoperability - Writing a Microsoft Bob application

2026-01-31T17:00:00+01:00 for 00:25

I stumbled upon a forum post of Jean, tasked in 2010 with recovering text documents for a friend from their broken Windows 95 computer. Their friend used Microsoft Bob, and the Microsoft Bob letter writer exclusively.

I was fascinated by this story, and then spent months reverse-engineering the Microsoft Bob APIs. Ultimately producing the first third-party Microsoft Bob application. During this I learned that Microsoft Bob isn't only a laughable flop, (The word "only" is doing a lot of work here), it also had strong ideas on what computing should be.

We will take a tour of Bob and its history and what I discovered about its technical underpinnings while reverse engineering.

Hopefully I can convince you that these stories are still relevant today, and can inform us on how we think about the software we use. But most importantly; the software we recommend our (non-techy) friends and family to use.

Introducing Hard-working, Easy going Software Everyone Will Use

View on FOSDEM site