Steve
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Illustrator currently doe snot support network drives or operations. However, the issue you describe seems to be operating system issue. Moving this as a feature request to support
KB: https://helpx.adobe.com/illustrator/kb/illustrator-support-networks-removable-media.html
An error occurred while saving the comment An error occurred while saving the comment Steve commented
I managed to find an ai file that was created with Illustrator CC 2017 and this fails in synchronization too so it is possibly a High Sierra problem. All other file types seem unaffected though - sync only fails for ai files.
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Problem persists with ai files created with 22.0.1