Hi Roy,
In regard to the issue that the “Send As” permission error, it usually caused by the permission you’ve granted isn’t set up correctly. To solve it, please try the steps below:
- Connect PowerShell to Exchange Online.
- Please run the “Get-RecipientPermission” command for the user(e.g. Get-RecipientPermission “Neo Yu”) in PowerShell, and see if the CEO is in the list.
- Refer Give Users Send As Permission to grant permissions for the CEO in PowerShell and try again.
- Refer A user who has Send As permission cannot send email messages as another user account in Outlook in Office 365 to try the resolution in the page, and try again.
Please feel free to post your updates here at your convenient time.