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 commentedI 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