The typical behavior is that the user will be able to print once or twice, then the printers in the cloud show as offline in the Printer Control Panel cloud application, and the user can no longer print.
There is no ETA for a fix as of 1/2/2019.
The temporary workaround is to disable ‘Scan Files When Written or Modified’ in the Shield settings. Most offices will have the local Webroot console locked down by policy, necessitating that the change be made on the back end, so your IT team will need to be contacted.
Once the local IT team has turned this setting off in the Webroot settings, reboot the computer, refresh the Webroot configuration by right-clicking on the tray icon, and try printing multiple times again. This should resolve the issue, although in some cases, technicians have had to uninstall Webroot entirely.
IMPORTANT: Implementing the above setting change, or uninstalling Webroot, is a major security concern. Once printing is verified working, have your local IT team log a ticket with Webroot support so that Webroot can track instances of this problem and inform the IT team when this issue is fixed, so that the setting can be changed back.