[ Yeah, it should have been -vvv and not --debug. I am missing up apps. :) My 
apologies. ] 




On August 5, 2019 at 4:45:33 PM, Andrew Morgan 
(alonsoamor...@gmail.com(mailto:alonsoamor...@gmail.com)) wrote:
> <54.236.183.46> ESTABLISH SSH CONNECTION FOR USER: andrewm
> <54.236.183.46> SSH: EXEC sshpass -d42 ssh -C -o ControlMaster=auto -o 
> ControlPersist=60s -o StrictHostKeyChecking=no -o 
> 'IdentityFile="/Users/confluencetrades/Desktop/andrewm.pem"' -o 
> 'User="andrewm"' -o ConnectTimeout=10 -o 
> ControlPath=/private/var/root/.ansible/cp/a3358dc28d -tt 54.236.183.46 
> '/bin/sh -c '"'"'sudo -H -S -p "[sudo via ansible, 
> key=fahckbxvjwfjuwfziuxflwkbjtwbsyfl] password:" -u root /bin/sh -c 
> '"'"'"'"'"'"'"'"'echo BECOME-SUCCESS-fahckbxvjwfjuwfziuxflwkbjtwbsyfl ; 
> /usr/bin/python 
> /home/andrewm/.ansible/tmp/ansible-tmp-1565048685.95-166747859799287/AnsiballZ_command.py'"'"'"'"'"'"'"'"'
>  && sleep 0'"'"''
> Escalation succeeded
> <54.236.183.46> (1, '\r\n', 'Shared connection to 54.236.183.46 closed.\r\n')
> <54.236.183.46> Failed to connect to the host via ssh: Shared connection to 
> 54.236.183.46 closed.

At this point, the only possible problem I can think of is sudo restrictions.

Are you sure you can run arbitrary commands via sudo on your box. My workplace 
doesn't let me execute shells via sudo, for example. We use a workaround to 
make sensible work.

e.g. Can you run on your remote box something like this?

    sudo /bin/sh -c "echo hello from bash; python -c 'print \"hello\"' "

- Sandip


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