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I'm trying to put together a Smart Group that contains Computers if either 1 of 2 applications is missing.

Currently I'm using

Application Title - does not have - "App1" OR Application Title - does not have - "App2"

I have computers listed that have App1 installed.  I know there are other computers that have App1 installed so I can't work out why only some computers are present.

 

Try using the parenthesis to separate the criteria. Since you're needing either one to be true, you actually need to evaluate two data sets, if you will. I mocked this up really quick using Chrome and Edge as the criteria. I first had only Chrome installed and the machine was in there. Once I installed Edge, the computer fell out. I then deleted Chrome and the computer came back.