The following on-prem cmdlet will change the value for a particular mailbox: This value must be changed to -1073741818. The default value on-prem for a mailbox that has been migrated to Exchange Online is -2147483642. This will allow the cloud user's mailbox to become ACLable. If you want to allow a cloud user to become a delegate of an on-prem user, you need to reconfigure the msExchRecipientDisplayType attribute for the remote user in on-prem AD. This is all you need to allow an on-prem user to become a delegate of a cloud user's mailbox. Set-OrganizationConfig -ACLableSyncedObjectEnabled $true
To enable cross premises delegation you first need to configure it in Exchange on-premises EMS with the following cmdlet: Gone are the days when you had to migrate users with delegated permissions at the same time to keep delegation working when migrating to Exchange Online. This is being rolled out to all Office 365 tenants by the end of April 2018. I'm happy to say that this is finally becoming a reality. Exchange hybrid organizations commonly ask about delegating mailbox permissions between on-premises and cloud users.
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