[judge2020]

Since it's the same company with access to both the first and second server, it wouldn't be too hard to log network on both ends and sync it up.

With iCloud Private Relay, it'd be harder for a single actor to de-anonymize requests; you'd either need collusion between the companies or a government entity would need to ask both companies to log network traffic at once, and this would complicate the "exit node" server since it can't filter/only record traffic from the target customer's connection without company 1 setting up a single server dedicated to being the proxy for that customer.