Hi Helen, Thanks for sharing the file, we are able to repro this at our end & yes it got broke in 2019. We are currently investigating this issue further. I would request you to report this issue as a bug on Illustrator User Voice (Adobe Illustrator Feedback) so that we can track it there also. As a workaround I suggest you to just move your sub-layer P3M1 outside the Clipped Artboard layer (It should be treated as a single layer) than you can use the "Expand Appearance" on this layer P3M1 and then drag the P3M1 layer back to the Clipped Artboard layer in its original position. Apologies for the inconvenience. With Best Regards, Raghuveer Singh Illustrator Team
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