See example 5 in http://dev.w3.org/csswg/css-shapes-1/#relation-to-box-model-and-float-behavior Right now, the content will only intrude into the outermost float, it should be able to pass through it to a previous float if there is no shape in the way.
Created attachment 221482 [details] Patch
Comment on attachment 221482 [details] Patch r=me
Comment on attachment 221482 [details] Patch Clearing flags on attachment: 221482 Committed r162217: <http://trac.webkit.org/changeset/162217>
All reviewed patches have been landed. Closing bug.