Dear bchleb
Welcome to the Microsoft community.
According to your description, it is unusual that after you log in again in New Outlook, access is often denied.
Recently, users in other countries have also reported similar problems. This matter is currently under investigation, and we would also like to collect some information from you:
- What is your New Outlook version? Click Settings - General - About Outlook to check the current version number.
- Is your current system version Windows or Mac? What is the specific version number?
- What type of account have you configured in New Outlook? Is it a Microsoft personal account such as @outlook.com@hotmail.com, or a Gmail account, or an IMAP/POP type third-party account? If you only configure one type of account, will you still encounter this problem?
We strongly recommend that you click Help-Feedback in New Outlook, describe the problem in detail, and click Send to notify the Outlook team, which is very helpful for quickly fixing the problem.
At present, we recommend that you use other methods to access your mailbox temporarily. The classic version of Outlook you mentioned is a paid Office software, which has been completely unbundled with New Outlook. If you have the classic version of Outlook installed on your computer, you can search for "outlook.exe" in the search bar to run it.
I will always pay attention to the development of this issue, and if there is any progress, I will inform you as soon as possible.
Thank you for your understanding and support.
Best wishes
Forry.F - MSFT | Microsoft Community Support Specialist