Hi Nick, I think you need a new matcher for that!

In EspressoTestsMatchers I would add:

public static Matcher<View> hasDrawable() {
    return new DrawableMatcher(DrawableMatcher.ANY);
}

And in the DrawableMatcher you can do something like this:

static final int EMPTY = -1;
static final int ANY = -2;
@Override
protected boolean matchesSafely(View target) {
    ...
    ImageView imageView = (ImageView) target;
    if (expectedId == EMPTY){
        return imageView.getDrawable() == null;
    }
    if (expectedId == ANY){
        return imageView.getDrawable() != null;
    }
    ...
}

Actually I think I should update my post with your request! The hasDrawable() matcher can be useful :)