The facilitator opens their laptop at 9am. There's already a file in the workspace folder — a briefing document generated at 8:30 AM, before they'd even made their tea.
"I didn't write this. I didn't run a prompt. Cowork did it while I was on the train. The briefing was waiting for me when I sat down. Tom in Ops calls it his 'robot PA'."
Now for the reality check: scheduled tasks run locally on your machine. Your laptop must be awake, Claude Desktop running, and internet connected. If any condition fails, the task silently skips. There is no cloud fallback, no retry, no notification. You won't know it failed unless you check.
In March 2026, a daylight saving time bug caused scheduled tasks to loop or skip entirely. This was patched, but it illustrates the brittleness of local scheduling. Cowork has also had multiple service outages (March 2, 17, and 22). Scheduled tasks that hit an outage just don't run.
Think of it as "set it and forget it until you close your laptop." Not bulletproof — but for daily and weekly routines, it's like having a colleague who starts work before you do.
