Have you gone through the Troubleshooting stuff for Garmin Express on Garmin's Support site?

https://support.garmin.com/en-US/?fa...nerrormessages

https://support.garmin.com/en-US/?pr...nerrormessages

https://support.garmin.com/en-US/?pr...768&tab=topics

Seldom have they helped me for those type issues. But they must have helped someone.

Also, call Garmin Support on the phone. You don't have to sit and wait in queue burning up your phone minutes. If the wait time is long, then their system will offer to take your call back number and when your turn in queue will have come up, then they'll call you back. But it'll probably be much of the same stuff, and if you aren't technically knowledgeable about your equipment that connects you to the internet, then that'll be a minus too.

January 1 was the last time I updated maps and other updates on several Garmin devices I have. No issues then and it was all fairly quick (in Garmin terms of quick) using a macbook and Garmin Express with wired Ethernet connection.