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I tested this. I have the opposite behavior :-/.
It is always going to run that trigger, no matter what the schemaUpdateMode setting is. #puzzled
Do notice that debugging does not seem to be an option.. . don't know if that is what you are trying to do...
@HunterFeltman-MSFT i am using the same code as in this document in the below link i additionally kept a message to check if the trigger is running or not.
I'm not familiar with this particular example code, however, I can tell you that the OnInstallAppPerCompany trigger is going to be run in a UI-less 'background' session and as such will never display messages to users, so unfortunately you would never see things in the client.
If you are sure that the 'IsExampleApplicaitonAreaEnabled' function should be responding back with 'false' then you could check the DB to see if 'EnabledExampleExtension' code has actually executed (though it also seems that there are more 'quit early' checks inside that)
If you want to be really sure, I suggest creating a simple dummy table & page and then populate said table in this code.
Note: Use the 'recreate' schemaUpdateMode to assert that data is cleared from this table before you F5 multiple times with this code.
You might have to adjust object ids, but with this you could then navigate directly to your page and see if data was inserted into the table (indicating that the trigger did, in fact, run)