Just playing around with KM trying out the “Type modifier” function.
I though this would turn “T” into “shift” but it doesn’t. What did I missed ? Thank you 
Keyboard Maestro will be simulating the shift key as pressed.
However any actual event made by anything else (eg pressing the keyboard) will still retain the normal modifiers.
Simulating holding the shift key down is not the same as physically holding the shift key down. The keyboard knows the shift key is not down and sends an appropriately unshifted T.
Thank you !