I poked around a bit more, and found a method to handle these kind of
situations: #rearmHandlerDuring:
You could rewrite the exception handling block to something like this:

[ :ex |

  ex tag == #getVMMaker
     ifTrue: [ ex resume: #caught ]

     ifFalse: [ ex rearmHandlerDuring: [ ex pass ] ] ]

and get five #cought on the Transcript