iCloud Sync on Mac

If you decided to use iCloud Drive:

1. Go to System Preferences > iCloud and login with your Apple ID, then check the box for iCloud Drive at the top of the list. A local iCloud Drive folder will appear in Finder right after that;

    TIP: If local folder doesn't appear in Finder, choose Finder > Preferences > Slidebar and
           enable iCloud Drive there.

2. Folder associated with Outline will be created automatically in iCloud Drive section. Place your notebook (if you already created it locally) into Outline folder;

How to move local notebook to the cloud storage

    TIP: If you want to migrate from Dropbox, just copy/paste your notebooks from Dropbox local
            folder to Outline folder in iCloud Drive.

3. In Outline choose + next to NOTEBOOKS in the navigation tree  >  Open from iCloud  >  navigate to iCloud Drive > Outline folder in Finder >  Select your notebook's folder  >  Open.

In case you want to create a new notebook, click + next to NOTEBOOKS  >  Create New Notebook  >  "Folder" icon to choose location  >  iCloud Drive folder > Outline >  Open  > Save.

Advantage of iCloud: You can recover deleted notebook files on icloud.com. Go to the iCloud Settings -> Restore files (Advanced section in the bottom left corner), select deleted files and click Done. 

You can sort the list by the date deleted for more convenience. Note that restored files will overwrite your current files. 

    NOTE: iCloud Drive doesn`t allow simultaneous edits, so make sure that you are editing your
               files on one device at a time only. Otherwise it will create conflict copies.

You might find useful: iCloud sync troubleshooting
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