Since we updated to 11.20.1 the UrlResolver will always resolve shortcuts. 

For example, see the result above the variable where the ancestor page that we are trying to lookup has the URL /pageurl

var ancestor = whateverIcontent; // url:/pageurl
if (ancestor is PageData pageData && pageData.LinkType == PageShortcutType.Shortcut)
{
    // url:/pageurl/page
    var asd1 = UrlResolver.Current.GetUrl(pageData);

    // url:/
    var asd2 = UrlResolver.Current.GetUrl(pageData.ParentLink);

    // url:/pageurl/page
    var asd3 = UrlResolver.Current.GetUrl(pageData.LinkURL); 

    // url:/pageurl/page
    var asd4 = UrlResolver.Current.GetVirtualPath(pageData);

    // url:/
    var asd5 = UrlResolver.Current.GetVirtualPath(pageData.ParentLink);

    // url:/pageurl/page
    var asd6 = UrlResolver.Current.GetVirtualPath(pageData.ContentLink);
}

If I'd like to resolve the url to the page at /pageurl that would be impossible using the UrlResolver. We made the update from 11.13.2 to 11.20.1, did I miss the release notes on that API change?