The Attach files button in the create-task dialog has always uploaded your files. The task just never showed them again. They were stored and they counted against your storage, but from the moment the task existed they were invisible.
The task screen now lists every file a task owns, and lets you add and remove files at any point in the task's life.
What is new
An Attachments section under the description, on the task page and in the board's side panel.
An Attach files button in the same place, so a file can join a task long after it was created.
Drag and drop anywhere on the task screen. Drop a log file on the panel and it attaches.
Two kinds of file, listed apart
A task collects files from two places, and the section keeps them separate.
Files you attached directly sit at the top, each with a remove control.
Images and file chips inside the description appear below them under From the description. They belong to the task just as much, but they are part of the text: remove one by editing the description and it leaves the list with it. That is why they carry no remove button of their own.
Details worth knowing
Anyone on the project can attach and remove files, not only the person who uploaded them.
A task holds up to 20 directly attached files. Images inside the description do not count towards that limit.
Dropping a file into the description editor still inserts it into the text rather than attaching it separately. That behaviour is unchanged, and the drop zone deliberately stays out of the editor's way.
Removing a file deletes it from storage when nothing else references it, so the space goes back to your plan.
get_taskin the MCP server now returns a task's attachments, so Claude Code can see the spec or log you attached while it works on the bug.
Nothing to do to enable any of this. Tasks you created weeks ago will show the files that were attached to them all along.