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Unlike my when using my Google Mail account, it looks that my Microsoft Outlook 365 folders are not automatically updated with incoming email messages. It seems to me that any new email items are updated probably once in 15-20 minutes. I know that i can update Outlook by hitting F9 or use the Send/Receive All command.
It's a Chrome bug with Gmail. Go to your Trash, then back to your Inbox and refresh your mail messages. The extension will update then. If you don't do this and you close the tab, then return to Gmail, it doesn't usually update things in Gmail properly either.