extend error message for timeouts to include more detail to user

[zgoldman-r7]

Partially addresses #6274 - specifically implements #6274 (comment) for all functions that use that timeout error.

Verification

List the steps needed to make sure this thing works
Short version - trigger any Rex::TimeoutError and verify more verbose text
Longer version:
For interactive:

• Start msfconsole
• Open up a reverse shell (ie in windows/meterpreter/reverse_http)
• `sessions -i your_session_id
• Send a command that triggers the timeout error (ie powershell_execute 'sleep 20; echo abc')
• Error should read "Send timed out. Timeout currently 15 seconds, you can configure this with sessions --interact --timeout "

For script:

• create a foo.rc file with the following contents:

<ruby>
puts run_single("load powershell")
puts run_single("powershell_execute 'sleep 20; echo abc'")
</ruby>

• start msfconsole
• sessions --script foo.rc your_session_id
• verify the output reads "Send timed out. Timeout currently 15 seconds, you can configure this with sessions --timeout --script <script> "

For command:

• start msfconsole
• Open up a reverse shell (ie in windows/meterpreter/reverse_http)
• sessions -C "load powershell" your_session_id
• sessions -C "powershell_execute 'sleep 20; echo abc'" your_session_id
• verify the output reads "Send timed out. Timeout currently 15 seconds, you can configure this with sessions -C --timeout "

[adfoster-r7]

Let's rename that final variable, and squash the commits down for git hygiene purposes

[adfoster-r7]

OSX osx/x64/shell_reverse_tcp

⚪ No timeout error printed, the timeout also seems to be lower than Meterpreter

msf6 payload(osx/x64/shell_reverse_tcp) > time sessions -i -1 -c 'sleep 20; echo abc'
[*] Running 'sleep 20; echo abc' on shell session -1 (127.0.0.1)

[+] Command "sessions -i -1 -c sleep\\ 20\\;\\ echo\\ abc" completed in 5.006230000006326 seconds

It looks like this is because the shell first tcp session has no configurable timeout

# osx/x64/shell_reverse_tcp
>> framework.sessions.values.last.methods.grep /timeout/
=> []
# osx Meterpreter
>> framework.sessions.values.first.methods.grep /timeout/
=> [:response_timeout, :response_timeout=, :comm_timeout, :comm_timeout

OSX Meterpreter

🔴 Looks like this doesn't work with the OSX Meterpreter with the -c flag

msf6 payload(osx/x64/meterpreter_reverse_tcp) > time sessions -c 'sleep 20; echo abc; echo abc'
[+] Command "sessions -c sleep\\ 20\\;\\ echo\\ abc\\;\\ echo\\ abc" completed in 14.324570000004314 seconds

The timeout exception is swallowed deeper down in the stack and the channel response is just read as being empty

Windows Meterpreter

🍏 Original windows UX improvement is working as expected:

meterpreter > powershell_execute 'sleep 20; echo abc'
[-] Send timed out. Timeout currently 15 seconds, you can configure this with sessions --interact <id> --timeout <value>

🍏 via sessions -C

msf6 exploit(windows/smb/psexec) > sessions -C "powershell_execute 'sleep 20; echo abc'"
[*] Running 'powershell_execute 'sleep 20; echo abc'' on meterpreter session 2 (192.168.123.133)

[-] Send timed out. Timeout currently 15 seconds, you can configure this with sessions -C <cmd> --timeout <value>

🍏 Works with the -c flag:

msf6 exploit(windows/smb/psexec) > sessions -i -1 -c 'powershell -command "Start-Sleep -s 20; echo abc"'
[*] Running 'powershell -command "Start-Sleep -s 20; echo abc"' on meterpreter session -1 (192.168.123.133)
[-] Operation timed out. Timeout currently 15 seconds, you can configure this with sessions -c <cmd> --timeout <value>

[adfoster-r7]

I don't think the OSX edgecase is a blocker, as we've made improvements to the powershell side of things now which was our main focus/target user workflow 👍

[adfoster-r7]

Release Notes

Improves error messages for timeouts when interacting with a Meterpreter session. Before an unclear error was printed. Now the user is notified how to increase the timeout limit.