I am looking to add checkboxes to NSOutlineview using the correct Apple recommended method - however its not clear from the documentation.

How do I add the behavour to allow users whereby if I click a parent checkbox, then it will select the children, and if I unclick it - it will deselect the children of that item?

edit: I have simplified my question and added image to make it clearer ( hopefully)

My Approach: I have been using the wonderful answer by Code Different to build an Outline view in my mac app. https://stackoverflow.com/a/45384599/559760 - I chose to populate the NSoutLine view using a manual process instead of using CocoaBindings.

I added in a stack view including a check box which seems to be the right approach:

My solution involves creating an array to hold the selected items in the viewcontroller and then creating functions for adding and removing

var selectedItems: [Int]?

@objc func cellWasClicked(sender: NSButton) {
    let newCheckBoxState = sender.state
    let tag = sender.tag
    switch newCheckBoxState {
    case NSControl.StateValue.on:
        print("adding- \(sender.tag)")
    case NSControl.StateValue.off:
        print("removing- \(sender.tag)")
    default:
        print("unhandled button state \(newCheckBoxState)")
    }

I identify the checkbutton by the tag that was assigned to the checkbox

In the interest of future Googlers I will repeat things I've written in my other answer. The difference here is this has the extra requirement that a column is editable and I have refined the technique.

The key to NSOutlineView is that you must give an identifier to each row, be it a string, a number or an object that uniquely identifies the row. NSOutlineView calls this the item. Based on this item, you will query your data model to populate the outline.

In this answer we will setup an outline view with 2 columns: an editable Is Selected column and a non-editable Title column.

Interface Builder setup

Select the first column and set its identifier to isSelected
Select the second column and set its identifier to title

Select the cell in the first column and change its identifier to isSelectedCell
Select the cell in the second column and change its identifier to titleCell

Consistency is important here. The cell's identifier should be equal to its column's identifier + Cell.

The cell with a checkbox

The default NSTableCellView contains a non-editable text field. We want a check box so we have to design our own cell.

CheckboxCellView.swift

import Cocoa

/// A set of methods that `CheckboxCelView` use to communicate changes to another object
protocol CheckboxCellViewDelegate {
    func checkboxCellView(_ cell: CheckboxCellView, didChangeState state: NSControl.StateValue)
}

class CheckboxCellView: NSTableCellView {

    /// The checkbox button
    @IBOutlet weak var checkboxButton: NSButton!

    /// The item that represent the row in the outline view
    /// We may potentially use this cell for multiple outline views so let's make it generic
    var item: Any?

    /// The delegate of the cell
    var delegate: CheckboxCellViewDelegate?

    override func awakeFromNib() {
        checkboxButton.target = self
        checkboxButton.action = #selector(self.didChangeState(_:))
    }

    /// Notify the delegate that the checkbox's state has changed
    @objc private func didChangeState(_ sender: NSObject) {
        delegate?.checkboxCellView(self, didChangeState: checkboxButton.state)
    }
}

Connecting the outlet

Delete the default text field in the isSelected column
Drag in a checkbox from Object Library
Select the NSTableCellView and change its class to CheckboxCellView
Turn on the Assistant Editor and connect the outlet

The View Controller

And finally the code for the view controller:

import Cocoa


/// A class that represents a row in the outline view. Add as many properties as needed
/// for the columns in your outline view.
class OutlineViewRow {
    var title: String
    var isSelected: Bool
    var children: [OutlineViewRow]

    init(title: String, isSelected: Bool, children: [OutlineViewRow] = []) {
        self.title = title
        self.isSelected = isSelected
        self.children = children
    }

    func setIsSelected(_ isSelected: Bool, recursive: Bool) {
        self.isSelected = isSelected
        if recursive {
            self.children.forEach { $0.setIsSelected(isSelected, recursive: true) }
        }
    }
}

/// A enum that represents the list of columns in the outline view. Enum is preferred over
/// string literals as they are checked at compile-time. Repeating the same strings over
/// and over again are error-prone. However, you need to make the Column Identifier in
/// Interface Builder with the raw value used here.
enum OutlineViewColumn: String {
    case isSelected = "isSelected"
    case title = "title"

    init?(_ tableColumn: NSTableColumn) {
        self.init(rawValue: tableColumn.identifier.rawValue)
    }

    var cellIdentifier: NSUserInterfaceItemIdentifier {
        return NSUserInterfaceItemIdentifier(self.rawValue + "Cell")
    }
}


class ViewController: NSViewController {
    @IBOutlet weak var outlineView: NSOutlineView!

    /// The rows of the outline view
    let rows: [OutlineViewRow] = {
        var child1 = OutlineViewRow(title: "p1-child1", isSelected: true)
        var child2 = OutlineViewRow(title: "p1-child2", isSelected: true)
        var child3 = OutlineViewRow(title: "p1-child3", isSelected: true)
        let parent1 = OutlineViewRow(title: "parent1", isSelected: true, children: [child1, child2, child3])

        child1 = OutlineViewRow(title: "p2-child1", isSelected: true)
        child2 = OutlineViewRow(title: "p2-child2", isSelected: true)
        child3 = OutlineViewRow(title: "p2-child3", isSelected: true)
        let parent2 = OutlineViewRow(title: "parent2", isSelected: true, children: [child1, child2, child3])

        child1 = OutlineViewRow(title: "p3-child1", isSelected: true)
        child2 = OutlineViewRow(title: "p3-child2", isSelected: true)
        child3 = OutlineViewRow(title: "p3-child3", isSelected: true)
        let parent3 = OutlineViewRow(title: "parent3", isSelected: true, children: [child1, child2, child3])

        child3 = OutlineViewRow(title: "p4-child3", isSelected: true)
        child2 = OutlineViewRow(title: "p4-child2", isSelected: true, children: [child3])
        child1 = OutlineViewRow(title: "p4-child1", isSelected: true, children: [child2])
        let parent4 = OutlineViewRow(title: "parent4", isSelected: true, children: [child1])

        return [parent1, parent2, parent3, parent4]
    }()

    override func viewDidLoad() {
        super.viewDidLoad()
        outlineView.dataSource = self
        outlineView.delegate = self
    }
}

extension ViewController: NSOutlineViewDataSource, NSOutlineViewDelegate {
    /// Returns how many children a row has. `item == nil` means the root row (not visible)
    func outlineView(_ outlineView: NSOutlineView, numberOfChildrenOfItem item: Any?) -> Int {
        switch item {
        case nil: return rows.count
        case let row as OutlineViewRow: return row.children.count
        default: return 0
        }
    }

    /// Returns the object that represents the row. `NSOutlineView` calls this the `item`
    func outlineView(_ outlineView: NSOutlineView, child index: Int, ofItem item: Any?) -> Any {
        switch item {
        case nil: return rows[index]
        case let row as OutlineViewRow: return row.children[index]
        default: return NSNull()
        }
    }

    /// Returns whether the row can be expanded
    func outlineView(_ outlineView: NSOutlineView, isItemExpandable item: Any) -> Bool {
        switch item {
        case nil: return !rows.isEmpty
        case let row as OutlineViewRow: return !row.children.isEmpty
        default: return false
        }
    }

    /// Returns the view that display the content for each cell of the outline view
    func outlineView(_ outlineView: NSOutlineView, viewFor tableColumn: NSTableColumn?, item: Any) -> NSView? {
        guard let item = item as? OutlineViewRow, let column = OutlineViewColumn(tableColumn!) else { return nil }

        switch column {
        case .isSelected:
            let cell = outlineView.makeView(withIdentifier: column.cellIdentifier, owner: self) as! CheckboxCellView
            cell.checkboxButton.state = item.isSelected ? .on : .off
            cell.delegate = self
            cell.item = item
            return cell

        case .title:
            let cell = outlineView.makeView(withIdentifier: column.cellIdentifier, owner: self) as! NSTableCellView
            cell.textField?.stringValue = item.title
            return cell
        }
    }
}

extension ViewController: CheckboxCellViewDelegate {
    /// A delegate function where we can act on update from the checkbox in the "Is Selected" column
    func checkboxCellView(_ cell: CheckboxCellView, didChangeState state: NSControl.StateValue) {
        guard let item = cell.item as? OutlineViewRow else { return }

        // The row and its children are selected if state == .on
        item.setIsSelected(state == .on, recursive: true)

        // This is more efficient than calling reload on every child since collapsed children are
        // not reloaded. They will be reloaded when they become visible
        outlineView.reloadItem(item, reloadChildren: true)
    }
}