osascript keystroke character case with VMware web console

Looking to get the ability to simulating typing a password into a vm console. Figured osascript and keystroke should be the answer. If I run the following I get what I believe to be the correct behaviour in the terminal.

#!/usr/bin/osascript
set UC to "ABCDEFGHIJKLMNOPQRSTUVWXYZÅÄÖ"
set lc to "abcdefghijklmnopqrstuvwxyzåäö"

#tell application "Safari" to activate
tell application "System Events"
  repeat with c in (the clipboard)
    considering case
      if UC contains c then
         key down shift
         keystroke "u" #c
         key up shift
      else
        keystroke "l" #c
      end if
    end considering
  end repeat
end tell

Result with stackEXCHANGE in clipboard:

➜  ~ ./send_keys.osa    
lllllUUUUUUUU%                                                                        ➜  ➜  ~  lllllUUUUUUUU

Adding the tell to activate Safari I expect something similar to end up in my VMware vm console terminal - however: The context is successfully switched to the Safari vm console window and the string is written correctly except all characters are lower case. The key down shift and key up switch which work fine in terminal (or in other web sites I tested), does **not** work in the vm console. How can I get keystroke to send characters in the correct case to the vm console? (Or - is there another way to get the string into the vm console?)