How to avoid issues with "Send on Behalf"

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Loopback

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Outlook version
Outlook 2019 32-bit
Email Account
Office 365 Exchange
Having issues finding a workable method for integrating my Phone, Desktop and OWA accounts.

Quick not about my setup, I have an Office 365 Family Premium Account. On my OWA account I have added four IMAP accounts from the mail servers of domains that I own and two GMail accounts.

This part works as I had hoped, mails are received on that account and then synced to my desktop and mobile Outlook app. The problem arises when I wish to reply to an email from other than my "official" outlook address. Then I get this message "This message could not be sent. You do not have the permission to send the message on behalf of the specified user"

If I resend it using my "official" outlook email address it goes thru fine. Obviously I would prefer that I would be able to send messages and reply to emails using the correct address. Is there a preferred method to solve this? Obviously if I add all of those accounts to my desktop Outlook the problem is resolved, however then there is an issue with syncing and duplicates. That solution also gets worse since I have a desktop, a laptop, a tablet and a phone.

I could also simply use OWA and drop the desktop but I want to have the maximum functionality that I feel a desktop application has. If anyone has a solution to this issue please share.
 
Were the addresses added as connected accounts on Outlook.com's Settings (gear icon) > View all Outlook settings > Mail > Sync Email?

Unless things changed, you should be able to send from outlook on the web using any alias - but in Outlook desktop it will send on behalf of the address if its not an outlook.com alias... but something is wrong because nothing is sending (from outlook desktop) except for the default address (even additional outlook.com aliases are failing.)
 
Yes, as you indicated, the accounts are under View all Outlook settings > Mail > Sync Email. And yes, even sending from accounts that are also an outlook alias in my microsoft account have the same issue. Good to know that it *should* work in Outlook Desktop, any thoughts on troubleshooting? I have tried pretty much every thing I can think of. The only one that has worked is adding that account to Outlook Desktop, but as I said, that is suboptimal ;> Or is there a better way to do this?
 
Because Microsoft is removing connected account support - only people with accounts added before last may can still use it (until they remove their last account) - my guess is they made some changes that changed how it works in Outlook. Even when it worked, messages were sent on behalf of.
 
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