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Requirements for SMTP App to "send-as" all users

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We have Exchange 2013 CU13 in a Hybrid configuration with Office 365.  We still have autodiscover (public & private) pointed to local Exchange.

Our in-house application needs to authenticate via SSL as Mailbox-A (on local Exchange) and Send-As any user's mailbox (in Office 365). The SMTP application points to mail.ourdomain.com, which resolves to our 2 Client Access Servers.

What are the Exchange and Office 365 requirements for getting this to work?


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