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A note about Permissions
File Sync and Attachment Sync use a callout to sync the file or attachment to S-Drive. So you must configure the outbound message user correctly:
Check Setup>outbound Messages for the following 3 items

• AttachmentSync

• FileSync Callout

• Preview Callout

Check the "user to send as" profile. It must have 

• Customize Application permission

• Send Outbound Messages permission

• Query All Files permission (which can only be applied using a permission set.)

• Session Security Level Required at Login must be None. It cannot be set to High Assurance
  

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Users who upload files that will be synced must also have

• Attachment Sync object profile permission (read/create/edit + field accessibility)

• Send Outbound Messages permission.