Please, I need help understanding why sometimes the user tag works and sometimes it doesn't. Some user sessions show the person's name, others appear anonymous. User tag has been set to css selector: body > div:nth-child(1) > div.company > div.info > h1
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So user tags are going to be unique to each defined application. If you have an application that always opens a homepage where the UI says "Hello <UserName>" then yes, it will grab it each and every time. But, If a user gets to your page via a method that skips your home page and does not show "Hello <UserName>" then they will be reported as anonymous. So what you can do is set a series of rules so no matter what page they are on, you are pointed to where their user name might be.
As mentioned this is application by application. SO if you Defined it out for Easy Travel, you will need to also define it out for NotSoEasyTravel even if they are in the same spot and the same CSS Selector.
Complementing Chad's reply, I would say that I have experienced several cases where User tags don't grab all users, with CSS selectors: