Outlook keeps saying "Trying to connect". How can I fix this?

This is BS. Ever since Microsoft tried to hard-sell me on 365, my outlook connection into the outlook app, which I paid for, keeps popping up with the password prompt. NONE of the so-called fixes provided by Microsoft work and I cannot get my mail to download to my local machine. This occurred with an update.

I do not want 365 subscription. I bought my app. Why does MS do this? Make life miserable?

Go into regedit

Computer\HKEY_CURRENT_USER\SOFTWARE\Microsoft\Windows\Currentversion\InternetSettings\Connections

Delete DefaultConnectionSettings and SavedLegacy Settings

Reboot

Here are the steps that seem to have fixed it for me. This was sent from a Microsoft Support tech.

Please try the following step:1. Close all Microsoft applications (such as Office, Teams, OneDrive, etc.).2. Search "%AppData%" in the Windows Search box and navigate to the Microsoft folder (C:\Users\3. Cut the "OneAuth" and "IdentityCache" folders out of the Microsoft folder and paste them onto your desktop.4. Relaunch Outlook and sign in. If the issue persists, close Outlook, copy the "OneAuth" and "IdentityCache" folders back into the Microsoft folder, and when it asks if you want to overwrite, say NO.5. Relaunch Outlook and sign in again to check if the issue is resolved.

The thing that seems to have made it work this time was finding all open microsoft office apps open even in the background and force quitting them with the task manager. I had tried it previously without doing that and it did not fix the issue.

I have seen that if you own a dell, uninstalling dell optimizer fixes this issue. Worked for me so far

Or try this

https://www.dell.com/support/kbdoc/en-us/000137415/how-to-disable-wireless-when-connected-via-wired-connection-on-latitude-and-precision-mobile-workstations#:~:text=Press%20F2%20during%20startup%20to,Wide%20Area%20Network%20(WWAN)

try the above first if you own a dell dock/laptop

Hello AJ Naudé,

Thank you for posting in the Microsoft Community. We are happy to help you.

Based on the troubleshooting steps you've already taken, it seems like you've covered most of the common solutions. However, there are a few additional steps you can try:

1. Check if there are any firewall or antivirus settings that may be blocking Outlook from connecting to the server. You can try temporarily disabling these settings to see if it resolves the issue.
2. Try creating a new Windows user profile and see if Outlook works on that profile. This can help determine if the issue is specific to the user's profile or if it's a system-wide issue. https://support.microsoft.com/en-us/windows/create-a-local-user-or-administrator-account-in-windows-20de74e0-ac7f-3502-a866-32915af2a34d
3. Check if there are any add-ins installed in Outlook that may be causing the issue. You can try disabling all add-ins and see if Outlook connects successfully. More on starting Outlook in safe mode and disabling add-ins.

If none of these steps resolve the issue, please let me know and we can explore other options.

Sincerely

Simbarashe | Microsoft Community Moderator