Using classic Outlook for Windows in business environments
Do you write the rules using a scripting language, or using the outlook rules tool? If the latter, maybe enough changed that it isn't recognized. If you used the tool, maybe you need to reenter them?
I have a rule triggering on the email from my daily backups, triggering on text to look for errors... with the exception of a phony error that sometimes happens. I just started a reboot of the NAS drive and then tried a backup. Naturally it failed.
On both PCs when the email came in, it popped up telling me about it. So the rule worked in two outlook versions in two windows versions.