User unable to send from additional Mailbox.

Hello all,
Here is the scenario that I am working with:
I have two users: Lucy and Jane. Lucy is Jane's boss, and has given Jane access to her mailbox to send/receive emails while Lucy is busy.
Jane is able to send email on behalf of Lucy as long as she stays logged in to her own account.
However, When logged into Lucy's account (as it was added as an additional profile to Outlook) Jane is unable to send any emails; they all get stuck in the outbox.
Both these users are O365 users, and we have verified that send/receive works in the OWA for both Lucy and Jane.
Jane is using the Outlook 2010 client on a Windows 7 machine.
Any information you could come up with would be of great assistance!

Hi,
If Jane wants to send as Lucy with an additional profile for Lucy account, Jane needs to have Send As permission instead of Send On behalf permission to Lucy's mailbox. To grant send as permission, we can run the following command in EMS:
Add-ADPermission -Identity Lucy -User Jane -ExtendedRights "Send As"
For more information about send as permission, please refer to:
http://technet.microsoft.com/en-us/library/bb676368(v=exchg.141).aspx
Regards,
Winnie Liang
TechNet Community Support
Thank you for the reply.
One thing should be mentioned: When jane is logged into her own profile in Outlook, she is able to send emails from Lucy's email completey fine. When Jane logs into Lucy's profile in Outlook, the emails all get stuck in the outbox.
In terms of the Send As permission, I would assume that Lucy has it as she is able to send email from Lucy's email when logged into Outlook on her own profile.

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User unable to send from additional Mailbox.

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