The hardest problem you ever worked on as a web developer?

Question

I get this question all the time for interviews, and I never have a good answer. In fact, it's possible if you do have a good answer for this question, it's because you're doing something wrong. But what do other people have?

speedgoose · Accepted Answer

Making a live video player work everywhere with as little latency as possible, without any interruptions, on shitty networks, from Internet Explorer 11 (in 2021) to Safari on iOS. But without webRTC because it would make way too much sense. Management never approved even testing WebRTC.
I made a version that worked okay with most network failures and browser failures. Not all, it’s impossible and I had zero motivation for that since I wanted to use WebRTC instead. I was going crazy.
I did quit and my old coworkers blame this video player, and they are right. But it was also because of the company strategy.

perilunar · Answer

The hardest problems are people problems. e.g. unrealistic deadlines, poor documentation, getting blocked waiting for other team members, inconsistent requirements, lack of accessibility testing, etc.

mod · Answer

I had to shoehorn a bunch of functionality into a shopping cart system for Ruby on rails called spree. I think it's named something else now.
The items could be extremely customized and that became very difficult, including things like calculating the cart price.
It also felt like the most fragile system I wrote, but to my knowledge it's still running about six years later.
The majority of my web work, though, was not very technically challenging.

psyklic · Answer

Nowadays I personally define a problem as "hard" if respected colleagues tried and failed to solve it.Earlier I would be reluctant to say a problem is "hard," because many of the best problems are not so much difficult as time-consuming.