The problem was not with z-index or position attributes, but with overflow. The tooltip did not work with "auto", but it worked with "visible." However, using 'overflow: visible;' you lose the automatic scrollbar on your windows, which is undesirable. So the best solution was to get the dynamic popup plugin to work with the parent sizes of the .ui-dialog-content div instead of the window size.
function getCropping(el) {
var w = $(el).closest('.ui-dialog-content');
var right = w.offset().left + w.width();
var bottom = w.offset().top + w.height();
var toolTipRight = el.offset().left + el.width();
var toolTipBottom = el.offset().top + el.height();
return [
el.offset().top <= w.offset().top,
right <= toolTipRight,
bottom <= toolTipBottom,
w.offset().left >= el.offset().left
];
}
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