When importing PSD files with layers into AI, if you 'outline', masks get deleted and transparency made 100%
When importing PSD files containing smart objects into AI, the masks get deleted and opacity reverts to 100% when you create outlines (and it is really dangerous cos I only export to AI as a last step before i print, so this can be easy to miss!!!!).
You can rasterize smart objects before exporting them as a work around, but that's not a great solution really, and means you are best creating a copy of the layer if you don't want to lose fidelity.
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You should send the file to sharewithai@adobe.com to help the team to investigate the problem
