If you use Outlook 2016 client, OneDrive client, Skype client or Apple Mail (version 12 on macOS Mojave), you will need verify only once until changes occurred in your account, such as changing the password or logging off the client.
If you use a browser for login, you potentially need to verify every time, unless you check the box “Don’t ask again for 60 days” to postpone the next verification for 60 days.