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At my previous company I administered a Microsoft 365 setup shortly after they switched over from an on premises AD setup with mixed results.

One bug which stuck out was trying to sync sharepoint directories with a length of over 255 characters locally on a windows machine with onedrive.

In Sharepoint you could create such directories and put files in them no problem through the webapp, but try to open a spreadsheet from the directory within windows file explorer and it would fail to open due to windows 255 character path limit.



I believe NTFS has support for 32767 char filenames (but 255 per level), but yes, Windows Explorer does not. Maybe in Win 11?




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