Note
October 6, 2026
2 min read
Why Was This Harder in DOTS?
By Cristiano Pierry
A failed upload turned a simple PDF task into a question about when a personal assistant actually makes work easier.
I’m still trying to understand when I should ask my dot for help instead of going straight to Codex. This time, I wanted to turn a photo of a document into a clean PDF.
The photo was a HEIC file on my Mac’s Desktop. Uploading it to dots produced “upload failed.” My dot suggested that the format might be the problem and that I should open Preview and convert it to JPEG myself.
Then the same file uploaded successfully in a new ChatGPT chat. That didn’t explain the failure in dots, but it made the format explanation less convincing. I was now troubleshooting the assistant before we had even started on the document.
I eventually launched a local Codex task. Codex found the photo on my Desktop, converted a copy, and read it. I asked it to flatten the photographed page, remove the surrounding borders, folds, and waves, and save a PDF on my Desktop. It delivered a flattened image and a one-page PDF.
That’s what frustrated me. The task was possible, and I got the result by asking Codex directly. In dots, I never got past the upload. A week into using dots, it still feels like a product working through its growing pains, and I’m not convinced it’s ready for a broader rollout.
I still don’t know what caused that failure. For me, a personal assistant earns its place by making a task like this easier to finish. After switching tools to get the file I wanted, I was left wondering:
Why didn’t I just start there?
This writing reflects my personal perspectives on product management, AI, and content discovery. It does not represent the official position of my employer or any affiliated organization.