There is one regression caused by the change for GROOVY-11029. I am testing a fix. The workaround is to remove static compilation or to write "other = 'value'" as "it.other = 'value'" so the "owner.delegate" gets applied properly.
class Bar { @groovy.beans.Bindable String baz String other } class Foo { Bar bar @groovy.beans.Bindable String foo @groovy.transform.CompileStatic void postConstruct() { bar = new Bar() bar.with { addPropertyChangeListener('baz') { event -> other = 'value' // ClassCastException: class Foo cannot be cast to class Bar print 'changed' } } print 'ready;' } } Foo foo = new Foo() foo.postConstruct() foo.getBar().setBaz('xxx') https://github.com/groovy/groovy-eclipse/issues/1412