Hi @jeffeld!
“Request to Webtask got ESOCKETTIMEDOUT” is commonly thrown when there is an issue in requests made from a custom database connection script, hook, or rule.
Have you tried adding some console.log()s in your rules to see if we can find more details on where the point of failure might be? You can also take a look at Real-time Webtask Logs extension to help gather more feedback as the webtask runs.
Please look at this community post that seems to be related to your issue for more ideas- http://community.auth0.com/t/request-to-webtask-got-esockettimedout/14687/10
Hope this helps. And feel free to direct message me the name of your Tenant and the rules you are using, I can investigate further.