@Finn, were you ever able to figure this out? We are having Windows Update issues now that we activated our Cisco Umbrella SWG. Umbrella is suggesting we use the Local Internet Breakout and use the DNS feature but that has not worked. I added about 6 Microsft Windows Update domains and updates are still not working. Trying to figure out all the different IP addresses used for Microsoft Updates will be nearly impossible. Meraki and Umbrella support haven't been able to figure out what's going on. Thanks.  ... View more