Hello IdiodicFly,
Thank you for using Apple Support Communities. It's my understanding that you're receiving an alert stating your iCloud settings are out of date when trying to access your iCloud Mail account in Outlook. The steps in the following resource may help:
Get help using Outlook with iCloud for Windows
If you're trying to generate an app-specific password, make sure that you have set up two-factor authentication and then try to generate a password on the Apple ID account page. Review the steps in the following resources:
Two-factor authentication for Apple ID
Using app-specific password
If you need to reset your Apple ID password, take a look at the resource below:
If you forgot your Apple ID password
Let us know the results. Please include specific error messages any troubleshooting steps you may have tried.
Have a nice day!