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As requested in this thread I moved this issue to a fresh set since it seems to be a separate issue I was able to reproduce two bugs with text flow around objects – as you can see in the attached file and screenshot, the flow breaks when there is either more than one mask on the element or if the masked element is in a group (and the flow around set for the group – in that case it seems to use the bounding box of the group for the text flow. This might actually be the intended behaviour, but it doesn't feel correct to me). The workaround is relatively easy by editing the wrapping contour by hand, but that kind of defeats the purpose of automatic wrapping around objects. When editing the contour manually I saw that the contour to start with was actually a bit off, which might have something to do with the other problems. dummy.afpub