While we integrate with all email services via SMTP and IMAP configurations, we have a special way to integrate with Outlook due to it's complexity with authentication. You can directly integrate with the company email and also with each individual worker.
If you have the following set while using the Outlook/Office365 integration:
Email Reply Address: Logged in User's Email
Then be aware that no matter who is sending the email, the customer will always see FROM as whatever email account was used to connect the company account with. If the customer hits Reply on the email, it will usually go back to the person who sent it and not the company email (but not in every scenario as some email clients don't respect this).
If you must have the email FROM and REPLY-TO always going back to the worker, then you'll need to setup email authentication for each person who will be sending emails. You can do this under Workers as an admin or ask your workers to do this by going to inflatableoffice.com/workers and clicking on Account-Profile.
Support for Outlook/Office365 email sending was added for worker profiles, so your worker can make changes, as long as you grant your worker permissions.