Hi,alan99
Welcome to the Microsoft forum.
Based on your description, it may be because the recipient's mailbox was moved or changed in some way during the upgrade process, and it is specific to users who use outlook and have sent it mails before, and it may be related to the cached autocomplete list, which can be cleared for all users who are unable to send mails to it: File->Option->Mail->Empty Auto- Complete List
Also,I recommend you to download the address book : Send/Receive-> Send/Receive Group->Download Address Book
I hope this helps.Please feel free to contact me for any updates.