When I select multiple rows in a NSOutlineView I would like to click on the checkbox of just one row and having selected all checkboxes.
Now, If I click on one checkbox only the clicked row row remains selected and only such checkbox is ticked.

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You’d have to write a handler for the checkbox action, that enumerated all the selected rows in the NSOutlineView, using selectedRowIndexes, then use those indexes in a loop to locate and setChecked the checkboxes.