We have seen issues with Office 365 SMTP configuration in most of the customer environments. Here are the steps that need to be done for Office 365 SMTP to work with Lepide using port 587.
Use the following server name: smtp.office365.com
Port: 587
SSL can be enabled or disabled.
The User provided in the configuration should have an Exchange Online license and should be an Exchange Administrator
TLS 1.2 is required on Lepide server
The User should have ApplicationImpersonation permission assigned. To do this:
Login to the Exchange Admin Center and go to Admin roles.
Click on Add Role Group
Provide a Name for this group
Click Next
Search for applicationimpersonation and enable it
Click Next
Now select the same user which was provided in the SMTP configuration in Lepide. Continue and and finish the process.
From the Exchange Admin Centre, select Settings, Mail Flow, Security Section, the option "Turn Off SMTP AUTH protocol for your organization" should be unchecked.
Go to Office 365 Admin center, Active Users, Search for the same user and go to the Mail section and select Manage Email Apps:
Under Manage Email Apps, the Authenticated SMTP option should be checked.