Hey Dick - thanks for your response.  I'm using sudo.  I bumped timeout to 
20s in ansible.cfg and now the playbook completes even with pipelining.  
While watching the -vvv output, I noticed "Escalation succeeded" after ~12 
seconds, so I think I was just barely hitting the timeout.  I still don't 
understand why it's timing out without attempting a connection (journalctl 
output), but honestly, I don't understand the state machine in ssh.py!  
Back in business though.

Rob

On Thursday, September 17, 2020 at 11:29:11 AM UTC-4 [email protected] 
wrote:

> Without knowing anything about those scripts, I would try
> adding/removing items to blob_ssodba_download_keys (so with 3 or 5
> items).
> This can reveal if the issue is with the 4th item - or with the last item.
>
> What is the privilege escalation method? I see the string 'oracle' -
> can it be some enterprise/corporate security measure that kicks in?
>
>
> On Thu, 17 Sep 2020 at 16:48, Rob Wagner <[email protected]> wrote:
> >
> > Hey all - I'm hitting the infamous Timeout (12s) waiting for privilege 
> escalation prompt error but only under specific conditions. The task that 
> fails is a loop:
> >
> > - name: copy files from blob
> > shell: "{{ blob_ssodba_download_working_dir }}/blob_ssodba_download.py 
> {{ item }} {{ blob_ssodba_download_dest_dir | 
> default(blob_ssodba_download_working_dir) }}"
> > with_items: "{{ blob_ssodba_download_keys }}"
> > become: "{{ blob_ssodba_become | bool }}"
> >
> > And blob_ssodba_download_keys contains for items. So the shell command 
> is running four times. The failure always occurs during the 4th iteration 
> of the loop. The error message with -vvv isn't useful:
> >
> > Using module file 
> /sso/sfw/virtualenv/ansible29/lib/python2.7/site-packages/ansible-2.9.9-py2.7.egg/ansible/modules/commands/command.py
> > Pipelining is enabled.
> > <azuseoracle01.vsp.sas.com> ESTABLISH SSH CONNECTION FOR USER: None
> > <azuseoracle01.vsp.sas.com> SSH: EXEC ssh -C -o ControlMaster=no -o 
> StrictHostKeyChecking=no -o GSSAPIAuthentication=no -o 
> KbdInteractiveAuthentication=no -o 
> PreferredAuthentications=gssapi-with-mic,gssapi-keyex,hostbased,publickey 
> -o PasswordAuthentication=no -o ConnectTimeout=10 
> azuseoracle01.vsp.sas.com '/etc/ansible-wrapper -c '"'"'sudo -H -S -p 
> "[sudo via ansible, key=yjyrdwfgvmqyevbiotnpzymsreknqtrd] password:" -u 
> root /etc/ansible-wrapper -c '"'"'"'"'"'"'"'"'echo 
> BECOME-SUCCESS-yjyrdwfgvmqyevbiotnpzymsreknqtrd ; 
> /usr/bin/python'"'"'"'"'"'"'"'"' && sleep 0'"'"''
> > fatal: [azuseoracle01.vsp.sas.com]: FAILED! => {
> > "msg": "Timeout (12s) waiting for privilege escalation prompt: "
> > }
> >
> > When I watch journalctl -f on the target, I notice a connection is not 
> even attempted during the fourth iteration of the loop. And the error only 
> occurs when pipelining is on.
> >
> > Any idea what might be going on?
> >
> > Rob
> >
> >
> > --
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> .
>
>
>
> -- 
> Dick Visser
> Trust & Identity Service Operations Manager
> GÉANT
>

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