Hey Nick, welcome aboard and thanks for sending over your project file.
If you take a look at your text with the subdiv surface, its a bit of a mess because the underlying text geometry is not even
It might be better to put the text into a REMESH to make it cleaner.
But in this case Im not sure why you’d need the Subdivision surface at all, if you just disable that it should work fine.
But its important to make sure all your objects have good topology when using the Boole or it will give unwanted results.
You could also try using the volume builder instead.