Shift key not captured in pwd field with Insert Text by Typing

I have been using an "Insert Text by Pasting" macro to enter my pwd for MS Remote Desktop (MRD).

However, after a few logins I can no longer paste into MRD'S pwd field (for reasons I don't understand, nothing appears), so I have to instead manually type in the pwd. I thus decided to create a new KBM macro for those situations, using Insert Text by Typing. However, it doesn't work because the shift key isn't recognized when using the macro to type into the pwd field. For example, when I use this:

What appears in the pwd field is instead this:


This is specific to the pwd field. If I instead use the macro within TextEdit, I get this:


I tried increasing the delay to 0.5 s, but it didn't fix the issue.

Unfortunately, remote desktops do not always properly process simulated events.

Since I can only simulate the events and can't tell when the application does with them after that point, I have no idea why they don't process the events correctly or what might be required to make it work (if anything is even possible).


Would simulating this more explicity (i.e., giving the system more step-by-step instructions) have a greater chance of success and, if so, if there a way to do this? For instance, could KBM give the system a series of instructions like:

Press and hold the shift key.
Type "h".
Release the shift key.
Type "ello"
Press and hold the shift key.
Type "1".
Release the shift key.