iOS A simple design question

Autoresizing works in relation to changes to the superview and not sibling views. I suspect what you'll need to do is programatically adjust the frames of these views in relation to the changes in the other views.

Various comments:

Typically views automatically resize when a) their superview resizes (automatically or not), b) after autorotation, and c) when a view controller is pushed. Other than that if you want to resize a particular view you need to have code somewhere that causes it to resize. That would usually be in its view controller or in its superview. layoutSubviews is common place for this kind of code to take advantage of the existing infrastructure to layout views.

Obviously the autoresizing behaviour is based on the autoresizeMask property. Not so obviously, autoresizing behavior is based on a superview-subview relationship. Peer views aren't involved in autoresizing. So if a superview is resized in code or because of a rotation it will resize its subviews. But it's not possible to directly express the relationship of two peer views to each other. You can only express the relationship of two peer views to their container view. If there needs to be a relationship beetween peer views it needs to be implemented in their containerView or view controller.

In your example I don't think there's an automatic way for a superview to resize based on its contents. You can't make viewDetails automatically get bigger because its subviews get bigger. You can however implement layoutSubviews in viewDetails to do this. You would then update the contents of the subviews and then send setNeedsLayout to viewDetails. For labels you can use sizeToFit to have them adjust their sizes to their contents. In the viewDetails layoutSubviews it would check the sizes of its subviews and then position them according to your design.