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There is apparently no way to insert widgets in a Treeview -- text only. See for instance https://stackoverflow.com/questions/16755176/tkinter-insert-a-combobox-inside-a-treeview-widget. I don't know whether clicks on a row can be pinpointed to a specific field (to pop up a widget), but it should certainly be possible to detect a right click to do the same. Or put treeview in frame with button with command that detect highlighted row. For your particular problem, I believe Treeview has a mode that allows multiple selections, with multiple rows highlighted simultaneously. If not, or in addition, replace proposed boxes with a blank column and insert string 'X' to indicate selection and inclusion in 'Install' or any other action.