Both menus should work the same way. Set the two different shortcuts and set both "Show menu on" options to None in Preferences/Start Menu #1 and #2.

Not sure I understand. Ending characters (which trigger the substitution) can be defined in Preferences/Text Expander. You can also select a "Trigger immediately" option.

What's new in FastKeys 4.16:
27th January 2019

Release notes:
- Optimized gestures context sensitivity,
- Updated translations,
- Several small improvements,
- Bug fixes

As always, your comments, suggestions or bug reports are highly appreciated.
Thanks!

Download FastKeys HERE!.

Tested on our computers and all characters are sent correctly. It could be that your console is using different input language. For example, when FastKeys sends a virtual key-code of the character :, the console wrongly interprets it as ^. Try in Notepad to see if it works.

This is not possible, internal shortcuts cannot be triggered by keystrokes produced by FastKeys.

If the command is the same there is no reason this would not work. For example, I tried the similar code below and it works in both, Shortcuts and Start Menu.

Maybe a short pause is needed before FileRead.

I'm not familiar with Bash. How you run is dependent on it's folder location on your system. Most probably you can run the script directly like this (one of the two should work): Run C:\Windows\System32\bash.exe /home/jjussi/randpass.sh Run C:\Windows\Sysnative\bash.exe /home/jjussi/randpass.sh Then...

You can use built-in variables like
A_WorkingDir
A_ScriptDir
A_WinDir
A_ProgramFiles
A_AppData
A_MyDocuments
etc...
https://www.autohotkey.com/docs/Variables.htm#prop

../ type syntax should also work.

By default, commands are never triggered by keystrokes produced by FastKeys. This avoids the possibility of an infinite loop where commands trigger each other over and over. By the way, your usage of StringSplit is incorrect, just use my script and only change "LongDate" to "dddd d MM...