Opening a new ticket in accordance to this comment on a different thread:
https://wpmudev.com/forums/topic/automate-has-issues-with-updating-wpml-plugin#post-1361246
The issue is that the Automate feature on the Hub seems to have issues updating certain plugins, and those plugins tend to be premium plugins like Gravity Forms, Events Calendar Add-ons, WPML, etc.
On my site, Gravity Forms is the main plugin that has consistently hard time updating. Right now it doesn't have an update pending since I updated it manually last time, but I would be happy to roll back to the previous version of Gravity Forms to help resolve the issue – just give me the word.
I gave access to support for my multisite and just now extended it for 3 more days since it was about to expire.
Let me know if you need anything else from me and I'll be happy to provide it!