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Windows SSO only works one way

Making moves

After an update, not which sure which, the Windows SSO setting only works going from personal outlook account to work account when selecting the profile icon in the upper-right. Both accounts are logged into Windows and no problem accessing resources. When going from Work account to Personal account, using the profile drop down menu, my personal account doesn't show and I have to go through the process of selecting "Sign in with a different account", select add a new account, type in personal account and after clicking sign-in, it doesn't ask for a password or OTP and just signs me in so why I can't just select the account from the profile drop down.