VBoxManage guestcontrol [vmname] run/start
I managed to open Calculator on my Windows 10 guest VM from my Ubuntu 23.04 host using the command:
VBoxManage guestcontrol $MY_VM_NAME run --exe "C:\\Windows\\System32\\calc.exe" --username $MY_USERNAME --password $MY_PASSWORD
Problem
However, when doing the same for WordPad, Microsoft Office applications or Adobe Acrobat Reader, it doesn't work:
VBoxManage guestcontrol $MY_VM_NAME run --exe "C:\\Program Files\\Windows NT\\Accessories\\wordpad.exe" --username $MY_USERNAME --password $MY_PASSWORD
Note: run and start give the same results.
Details
On the Ubuntu host, when I execute the last command, the cursor flashes and the prompt is never returned. In the Windows 10 VM, looking at the Task Manager, I note that the application (WordPad in this example) appears in the background processes list. When I try, using the same command, to execute a personal script I've converted into .exe file instead of an application, the outputs I'm used to see in the guest Windows "Terminal" appear in the host Ubuntu Terminal (see Test section below). It is like if the guestcontrol process attempts to redirect the output of the app to the host. However, I don't know why I have no problem when opening Calculator.
Using the --verbose option returns:
$ VBoxManage guestcontrol $MY_VM_NAME start --verbose --exe "C:\\Windows\\System32\\calc.exe" --username $MY_USERNAME --password $MY_PASSWORD
Executing:
Image : C:\Windows\System32\calc.exe
arg[0]: C:\Windows\System32\calc.exe
Creating guest session as user 'toto'...
Waiting for guest session to start...
Successfully started guest session (ID 8)
Starting guest process ...
[1284 - Session 8]
Wait result is 'started' (1)
Process successfully started!
Guest session detached
$ VBoxManage guestcontrol $MY_VM_NAME start --verbose --exe "C:\\Program Files\\Windows NT\\Accessories\\wordpad.exe" --username $MY_USERNAME --password $MY_PASSWORD
Executing:
Image : C:\Program Files\Windows NT\Accessories\wordpad.exe
arg[0]: C:\Program Files\Windows NT\Accessories\wordpad.exe
Creating guest session as user 'toto'...
Waiting for guest session to start...
Successfully started guest session (ID 9)
Starting guest process ...
[8812 - Session 9]
Wait result is 'started' (1)
Process successfully started!
Guest session detached
Ubuntu, Windows and VirtualBox tested versions
I got same results for both VirtualBox v6.1 and v7.0. I've also tried with VMs created from Win10_21H2_English_x64.iso and Win10_22H2_English_x64v1.iso. However, no matter the version of VirtualBox, if I'm using Ubuntu 22.04, then it works perfectly.
EDIT 1: Exact same behavior on Ubuntu 23.10 than on Ubuntu 23.04.
EDIT 2: The problem is still going on with VirtualBox v7.0.12.
Test
I've create a HelloWorld script that I converted to an executable file on the guest. From the host, when I do
toto@toto-pc:~$ VBoxManage guestcontrol $MY_VM_NAME run --exe "C:\\Users\\Toto\\Desktop\\runapp\\runHello.exe" --username $MY_USERNAME --password $MY_PASSWORD
Hello, World!
toto@toto-pc:~$
note that "Hello, World!" shows up in the Terminal of my host instead of the guest.

"C:\\Program\ Files\\Windows\ NT\\Accessories\\wordpad.exe".runseems to wait forwordpaduntil it's closed whilestartinstead worked as expected ... So try that like:VBoxManage guestcontrol $MY_VM_NAME start --exe "C:\\...... If that didn't work then most likely it's a Windows issue.startis most likely certainly the one to use for your purpose.