Users Outlook (O365) periodically just stops receiving mail.

And all three of them are O365? Are they all on different tenants?

All O365, same domain, same tenant.

I was just logged into the computer while making all of the changes above and it again, stopped receiving mail, I did a CTRL click on the Outlook icon to check connection status and everything is connected. Once I hit reconnect emails started coming in again.
 
All O365, same domain, same tenant.

I was just logged into the computer while making all of the changes above and it again, stopped receiving mail, I did a CTRL click on the Outlook icon to check connection status and everything is connected. Once I hit reconnect emails started coming in again.

Ok, if you have THREE O365 logins on one outlook, all aimed at the same Tenant then... your client is correct you don't know WTF you're doing. But it's an easy thing to fix.

There should be ONE login, hers... then you go into O365's admin portal and you give her read and manage permissions on the other mailboxes, send as permissions if needed possibly. Outlook will populate all three mailboxes to her Outlook for you.

You should never have more than 1 login in Outlook aiming at the same O365 tenant, you have tools to handle that work, you need to use them.

Fix the permissions, nuke her outlook profile and have her login, it'll put everything back as a single managed entity.

Technically the multiple separate logins should work... but that's intended for multi-tenant access. I have no idea what a single Outlook being managed three times by the same rule set will do.
 
Ok, if you have THREE O365 logins on one outlook, all aimed at the same Tenant then... your client is correct you don't know WTF you're doing. But it's an easy thing to fix.

There should be ONE login, hers... then you go into O365's admin portal and you give her read and manage permissions on the other mailboxes, send as permissions if needed possibly. Outlook will populate all three mailboxes to her Outlook for you.

You should never have more than 1 login in Outlook aiming at the same O365 tenant, you have tools to handle that work, you need to use them.

Fix the permissions, nuke her outlook profile and have her login, it'll put everything back as a single managed entity.

Technically the multiple separate logins should work... but that's intended for multi-tenant access. I have no idea what a single Outlook being managed three times by the same rule set will do.

Will try to delegate full access to the other accounts and see how that goes
 
That is the proper way. Set up a single Outlook profile, give her full access to the other mail boxes. In Outlook under account settings, click the main email address, click change, add a mailbox, add the other 2 mailboxes there. When you do, it should put them as separate headings on the left side under the main set of folders. User should then be able to see all once they sync.
 
That is the proper way. Set up a single Outlook profile, give her full access to the other mail boxes. In Outlook under account settings, click the main email address, click change, add a mailbox, add the other 2 mailboxes there. When you do, it should put them as separate headings on the left side under the main set of folders. User should then be able to see all once they sync.

That add mailbox bit is incorrect. Current Exchange clients are automatically configured by Exchange. The only time you have to add them manually is when your auto-discover is broken. Which does bring up something else to check... wouldn't hurt to run the DNS checks in the admin panel.
 
Ok, if you have THREE O365 logins on one outlook, all aimed at the same Tenant then... your client is correct you don't know WTF you're doing. But it's an easy thing to fix.

There should be ONE login, hers... then you go into O365's admin portal and you give her read and manage permissions on the other mailboxes, send as permissions if needed possibly. Outlook will populate all three mailboxes to her Outlook for you.

You should never have more than 1 login in Outlook aiming at the same O365 tenant, you have tools to handle that work, you need to use them.

Fix the permissions, nuke her outlook profile and have her login, it'll put everything back as a single managed entity.

Technically the multiple separate logins should work... but that's intended for multi-tenant access. I have no idea what a single Outlook being managed three times by the same rule set will do.

Just wanted to report back on this ... two days since I reconfigured and delegated full access to the other boxes as opposed to adding them directly to Outlook and she has not reported any further issues.

Strange since I know I have other clients with multiple email addresses from the same tenant configured in Outlook but I'm just going to stick this in the back of my head and move on.

Thanks for the idea.
 
I hope it holds, not sure why it fixes it... but simpler is always better! Let Exchange do that junk, it's good at it!
 
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