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GitHub introduced some time ago Task lists.

What are the minimum permission I need to set-up so collaborators/assignees are able to tick those boxes on the issue of the project?

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You need to give write access to your repository, as checking off a task list item in an existing comment is an edit action.

This is the explanation which I've received from GH support:

We have discussed the possibility of offering a more refined permission scheme. There, people will be able to edit issues, but not push to that repository. I am afraid I don't have anything concrete I can promise currently though. Our team will consider it.

See also: GH #590 - Give permission to project members to check off a task list items, without ability to push (unofficial issue tracking repo)

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On the wiki, it may be that collaborators are by default able to check of the boxes on issues/pull requests, since they can edit them.

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