SMTP Virtual Server and Exchange 365

just recently purchased office 365 premium for our users and will eventually migrate them from our on-premise exchange server to the exchange online. The problem is before i migrate i need to make sure that all of the current programs we run that forward email alerts and messages will still work when being directed to the office 365 exchange server. I created a SMTP virtual server on one of my servers and configured it to send outbound mail to the exchange 365 server. I am able to drop the email.txt file into the pickup folder and get it to work as long as I put the from address in the txt file to match the authentication email and address on the SMTP outbound security settings. As soon as I change the from address or try to send an email through another server application i will get a badmail message

iagnostic-Code: smtp;550 5.7.60 SMTP; Client does not have permissions to send as this sender []

The message is the same when i try from a server application except it sets the from address to
From: postmaster@machinename.domain.local
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David Johnson, CD, MVPOwnerCommented:
you have to have a mailbox that is authenticated in order to send mail.  so change the from address.

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Do you have Exchange on-prem? How many users you intending to move to Office365?
Generally, you can try this approach.
Marshal HubsEmail ConsultantCommented:
Link provided by Ronin has sufficient information. I would suggest you to use Stellar EDB to PST Converter to migrate mailboxes from Exchange Server to Office 365. The software can migrate multiple mailboxes to office 365. For more information, please check this link:

If you need any help, please let me know!!
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Sandeep KumarAssociate ConsultantCommented:
You can migrate on-premise Exchange server EDB file to Office 365 by using Kernel for Exchange Server Recovery software. One can easily export EDB file from any device from anywhere. It can repair the Exchange EDB file which is corrupted before or during migration. To know more about the process and download the tool, visit:
Todd NelsonSystems EngineerCommented:
Do you plan to be implementing directory synchronization via AAD Connect?
natevelli2Author Commented:
It was an issue with the authentication but I also had to hard code the from address in the application that was passing the report off to the relay server
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