How to make a custom view resize with the window with Cocoa Auto Layout?

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With Auto Layout, there are (at least) three possible ways to constrain a view so that it occupies the entire window’s content view, resizing when appropriate.

Visual format constraints with regard to superview

NSView *contentView = [_window contentView];
MyView *customView = [[MyView alloc] initWithFrame:[contentView bounds]];
[customView setTranslatesAutoresizingMaskIntoConstraints:NO];

[contentView addSubview:customView];

NSDictionary *views = NSDictionaryOfVariableBindings(customView);

[contentView addConstraints:
    [NSLayoutConstraint constraintsWithVisualFormat:@"H:|[customView]|"
        options:0
        metrics:nil
        views:views]];

[contentView addConstraints:
    [NSLayoutConstraint constraintsWithVisualFormat:@"V:|[customView]|"
    options:0
    metrics:nil
    views:views]];

Programmatic constraints for the edges

(this should be equivalent to the visual format above)

+ (void)addEdgeConstraint:(NSLayoutAttribute)edge superview:(NSView *)superview subview:(NSView *)subview {
    [superview addConstraint:[NSLayoutConstraint constraintWithItem:subview
        attribute:edge
        relatedBy:NSLayoutRelationEqual
        toItem:superview
        attribute:edge
        multiplier:1
        constant:0]];
}

and

NSView *contentView = [_window contentView];
MyView *customView = [[MyView alloc] initWithFrame:[contentView bounds]];
[customView setTranslatesAutoresizingMaskIntoConstraints:NO];

[contentView addSubview:customView];

[[self class] addEdgeConstraint:NSLayoutAttributeLeft superview:contentView subview:customView];
[[self class] addEdgeConstraint:NSLayoutAttributeRight superview:contentView subview:customView];
[[self class] addEdgeConstraint:NSLayoutAttributeTop superview:contentView subview:customView];
[[self class] addEdgeConstraint:NSLayoutAttributeBottom superview:contentView subview:customView];

Programmatic constraint for the size

NSView *contentView = [_window contentView];
MyView *customView = [[MyView alloc] initWithFrame:[contentView bounds]];
[customView setTranslatesAutoresizingMaskIntoConstraints:NO];

[contentView addSubview:customView];

[contentView addConstraint:
    [NSLayoutConstraint constraintWithItem:customView
        attribute:NSLayoutAttributeWidth
        relatedBy:NSLayoutRelationEqual
        toItem:contentView
        attribute:NSLayoutAttributeWidth
        multiplier:1
        constant:0]];
[contentView addConstraint:
    [NSLayoutConstraint constraintWithItem:customView
        attribute:NSLayoutAttributeHeight
        relatedBy:NSLayoutRelationEqual
        toItem:contentView
        attribute:NSLayoutAttributeHeight
        multiplier:1
        constant:0]];

The third approach is the one listed in the question and it may not work if there are further constraints. For example, without:

[customView setTranslatesAutoresizingMaskIntoConstraints:NO];

the original autoresize mask is applied as well, which leads to the behaviour described in the question: the window isn’t resized.

As mentioned by Regexident, you can use:

[_window visualizeConstraints:[contentView constraints]];

to debug Auto Layout. It’s worth checking the console output as well.

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