Hi @Donny Limbert
You mentioned you are able to do this in previous version of Outlook; do you mean Legacy Outlook or version 16.106 of New Outlook Mac?
From my testing, New Outlook for Mac only support server-side rules, it does not support client-side rules like Legacy Outlook.
However, "OR" does exist but only within the same condition. For example, I have Condition "From" and I have 2 senders (Admin and Lee Gu), it means that if Admin OR Lee Gu send to me, the condition will be triggered.
In conclusion, if you have multiple values in 1 condition, it is OR. If you have many conditions, they will be linked with AND (FROM and SUBJECT INCLUDES).
You can also provide how do you want your rule look like, I will try my best to assist you, either combine all the conditions in 1 rule or create 2 separated rules.
I look forward for your reply.
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