Using New Outlook on Windows for personal email, calendar, and contact management
The Outlook new solution & fix was complicated. Since I couldn't receive email I decided to try asking CoPilot in an Edge browser. The AI worked through the problem solving tree starting with the most likely solutions and proceeding from there. It provided a lot of step by step detail that I needed & like to have and offered to walk me through them, which I accepted. With every step that didn't work it had another step ready to try as one problem was ruled out. It is solved now, but only after 2 1/2 hours of "conversation" with CoPilot. And that was easier for me than the stress of talking with a human for that length of time. Your solution will likely be different than mine, so I encourage you to try CoPilot, just allow enough time to problem solve it. Here is a summary though of what I and CoPilot found:
The Outlook New application sign in repeatedly forced my Gmail address into a Microsoft sign‑in loop, making it impossible to open Outlook or access my email. This was not a simple login issue — it was caused by a deeper flaw in how Outlook handles Microsoft account aliases.
My Gmail address had been added as a Microsoft account alias years ago. Even after removing it from my Microsoft account online, New Outlook continued to treat that Gmail address as a Microsoft identity and forced me into a Microsoft login flow every time I opened the app and that would fail every time endlessly. The app refused to open offline, refused to bypass the Microsoft login screen, and ignored the fact that the alias had been removed. Resetting the app, clearing credentials, and repairing Outlook did nothing. The only way to break the loop was to manually change my primary Microsoft alias (to an outlook.com email address which I already had), remove the Gmail alias entirely from my Microsoft account, and then re‑authenticate the app using my Outlook.com address. Then I simply had to add my gmail address into Outlook New and make it primary.
Now Outlook New is working ok except I still get the olk.exe Entry Point not Found error message box that I have to close. I will try and solve this with CoPilot in the next few days.
I hope this helps.
[PII: Removed]