web_delivery, powershell, SSL and you

Powershell delivery for metasploit payloads has become extremely popular for its flexibility and AV avoidance.

Metasploit recently deprecated psh_web_delivery with web_delivery which offers the ability to deliver Ruby, Python, and Powershell payloads over a webserver.



psh_web_delivery deprecated



New web_delivery module



One of the nice features is the ability to serve payloads over SSL helping to avoid detection however the default syntax will not function correctly with a self signed certificate


Executing web_delivery

Executing web_delivery


I removed the “-w hidden” command so we can see the output instead of having it execute, fail, and close the window.


Self signed SSL error

Self signed SSL error

Self signed SSL certificate could not be trusted and execution fails


However you can suppress the SSL certificate validation by adding “[System.Net.ServicePointManager]::ServerCertificateValidationCallback = {$true}”


Disable SSL validation

This results in successful download and execution of the powershell payload.

When I first ran into this issue I couldn’t find any posts directly related to metasploit or powershell payloads and SSL validation after some digging I found this command.

Hopefully this saves someone else a few minutes of troubleshooting.



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Posted in InfoSec, metasploit

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