It appears U systems do have some ability to match name & number. My wife has changed her legal name but the change at United is taking a great deal of time. I have purchased several tickets for her with this mismatch.
The ticket I purchased via ual.com allowed me to enter her number & new name and it was not until we got to the airport that they told us her number was "incorrect". We explained and the agent put in an override. Told us to keep the ticket stub so she could verify flight if necessary.
The 1K reservations agent mentioned the mismatch as I bought a ticket for us via that channel. She also entered an override.
Hopefully United will update the records and we won't keep running into this problem.