The last day of Legalweek 2022 brought back a long running tradition for another year—though this time with a slight twist. Like years past, the "Annual Legalweek Judges Debate, Advocacy Under the Federal Rules and Rule 1.1" session included commentary from a number of judges on the most pressing e-discovery and electronically stored information (ESI) issues of the day. But this year, judges were invited to act as counsel in hypothetical cases concerning a complex discovery dispute, with the audience serving as the judge.

The session covered three hypothetical cases involving cloud-based email links, "discovery-on-discovery" due to past data retention failures, and 502(d) orders. Below, we look at the first two cases, and dive into the specific challenges the issues are creating for courts around the country.