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“Follow Session Folder” doesn’t seem to auto-switch Transfer Paths for me.

In version 5.x or higher and macOS 10.14 and higher you need to give Screen Recording permission now in System Security preferences.

Check This Article for more information about Security/Preference settings

Additionally, you need to check this option in Pro Tools Preferences¬†> Operation > Misc > Local Waveform Cache Versions and ensure it is set to 0…. Another weird PT quirk: