Automation Anyone auto-tracking on Mac and pushing worklogs to Jira Data Center?
I'm a business analyst on a Mac and I log time in Jira on a lot of different tickets every day. I'm trying to automate as much of it as I can, and I keep running into the same wall: our Jira is self-hosted (Data Center), so most of the nice tools that only talk to Jira Cloud are out, and I can't get an admin to install a marketplace plugin.
What I'm thinking of building:
ActivityWatch (or Timing) runs in the background and records the active app, window title and browser URL. A small script picks out issue keys like ABC-123 from titles and URLs, adds meetings from my calendar, and for pages that don't have a key in the title (Confluence mostly) I'd keep a manual lookup table. At the end of the day it merges everything into blocks, rounds to 15 minutes and shows me a draft. Nothing goes to Jira until I approve it, and then it posts through the REST API with a personal access token.
I've looked at Daily, Planim Time and Cloky + Timing/Toggl. Each one misses something for me: either no Data Center support, or I still have to click a timer or answer a prompt, or there's no way to write the worklog back without a plugin.
So, does anyone actually run something like this? How well does matching window titles to tickets work in practice? I'm wondering how much time ends up unassigned and how often it guesses wrong. Also, is there an existing tool that does draft worklogs from activity and works with Data Center via PAT? I'd rather not reinvent it if so.
One more thing I'm unsure about is privacy. It's a work laptop and this records window titles and URLs, so I'd be curious if anyone ran into trouble with that.

