With fresh eyes on the problem today, the last response in the GitHub issue 
clicked for me. I was defining "user@ip" in my ansible hosts file, instead 
of declaring the user with the `--user=` flag in the playbook command. 
Solved my own problem, hopefully this helps someone else.

On Tuesday, August 23, 2016 at 8:22:05 PM UTC-4, jguil...@g.harvard.edu 
wrote:
>
> Hi there,
>
> I'm new to Ansible, and jumping into it for a project at work. Right now 
> I'm trying to update our AWS instance machine using ansible-playbook. More 
> specifically, I'm running 
> ansible-playbook --private-key ~/keys/OasSDev.pem --sudo linux-toolbox.yml 
> -vvv
>
>
> What I'm getting is that this (with IP edited out):
>
> ansible-playbook --private-key ~/path/to/key.pem linux-toolbox.yml -vvv
>
>
> No config file found; using defaults
> [DEPRECATION WARNING]: Instead of sudo/sudo_user, use become/become_user 
> and make sure 
> become_method is 'sudo' (default).
> This feature will be removed in a future release. 
> Deprecation warnings can be disabled by setting deprecation_warnings=False 
> in ansible.cfg.
> Loaded callback default of type stdout, v2.0
>
>
> PLAYBOOK: linux-toolbox.yml 
> ****************************************************
> 1 plays in linux-toolbox.yml
>
>
> PLAY [linux-toolbox] 
> ***********************************************************
>
>
> TASK [setup] 
> *******************************************************************
> <ubu...@my.ip.goes.here> ESTABLISH SSH CONNECTION FOR USER: ubuntu
> <ubu...@my.ip.goes.here> SSH: EXEC ssh -C -vvv -o ControlMaster=auto -o 
> ControlPersist=60s -o 'IdentityFile="/Users/jguillette/keys/OasSDev.pem"' 
> -o KbdInteractiveAuthentication=no -o PreferredAuthentications=gssapi-with
> -mic,gssapi-keyex,hostbased,publickey -o PasswordAuthentication=no -o User
> =ubuntu -o ConnectTimeout=10 -o ControlPath=/Users/jguillette/.ansible/cp/
> ansible-ssh-%h-%p-%r ubu...@my.ip.goes.here '/bin/sh -c '"'"'( umask 77 
> && mkdir -p "` echo 
> $HOME/.ansible/tmp/ansible-tmp-1471991079.97-57666739369328 `" && echo 
> ansible-tmp-1471991079.97-57666739369328="` echo 
> $HOME/.ansible/tmp/ansible-tmp-1471991079.97-57666739369328 `" ) && sleep 
> 0'"'"''
> <ubu...@my.ip.goes.here> PUT /var/folders/k8/
> g7tw63ps1xx8dl39rs6p6nfh91wzbh/T/tmpgow_gt TO /home/ubuntu/.ansible/tmp/
> ansible-tmp-1471991079.97-57666739369328/setup
> <ubu...@my.ip.goes.here> SSH: EXEC sftp -b - -C -vvv -o ControlMaster=auto 
> -o ControlPersist=60s -o 
> 'IdentityFile="/Users/jguillette/keys/OasSDev.pem"' -o 
> KbdInteractiveAuthentication=no -o PreferredAuthentications=gssapi-with-
> mic,gssapi-keyex,hostbased,publickey -o PasswordAuthentication=no -o 
> User=ubuntu 
> -o ConnectTimeout=10 -o ControlPath=/Users/jguillette/.ansible/cp/ansible-
> ssh-%h-%p-%r '[ubu...@my.ip.goes.here]'
> fatal: [ubu...@my.ip.goes.here]: UNREACHABLE! => {"changed": false, "msg": 
> "SSH 
> Error: data could not be sent to the remote host. Make sure this host can 
> be reached over ssh", "unreachable": true}
>  [WARNING]: Could not create retry file 'linux-toolbox.retry'.         [
> Errno 2] No such file
> or directory: ''
>
>
>
>
> PLAY RECAP 
> *********************************************************************
> ubu...@my.ip.goes.here       : ok=0    changed=0    unreachable=1   
>  failed=0
>
> I'm able to ssh into the remote machine, and I'm able to connect with sftp 
> via this command:
>
> sftp -vvv -o ControlMaster=auto -o ControlPersist=60s -o 
> 'IdentityFile="/Users/jguillette/keys/OasSDev.pem"' -o 
> KbdInteractiveAuthentication=no -o PreferredAuthentications=gssapi-with-
> mic,gssapi-keyex,hostbased,publickey -o PasswordAuthentication=no -o 
> User=ubuntu 
> -o ConnectTimeout=10 -o ControlPath=/Users/jguillette/.ansible/cp/ansible-
> ssh-%h-%p-%r 'ubu...@my.ip.goes.here'
>
>
> Original for comparison, removed the flags -b - -C and the brackets around 
> the user@ip:
> sftp -b - -C -vvv -o ControlMaster=auto -o ControlPersist=60s -o 
> 'IdentityFile="/Users/jguillette/keys/OasSDev.pem"' -o 
> KbdInteractiveAuthentication=no -o PreferredAuthentications=gssapi-with-
> mic,gssapi-keyex,hostbased,publickey -o PasswordAuthentication=no -o 
> User=ubuntu 
> -o ConnectTimeout=10 -o ControlPath=/Users/jguillette/.ansible/cp/ansible-
> ssh-%h-%p-%r '[ubu...@my.ip.goes.here]'
>
> I'm not sure if I need to make some edits to my local Ansible 
> configuration, or if there are some issues on the remote. I found an issue 
> on GitHub <https://github.com/ansible/ansible/issues/16066> that sounds 
> like what I'm seeing, but I haven't been able to turn that into a working 
> solution. I did look at /etc/ssh/sshd_config and didn't find anything 
> related to sftp. That seems like a problem, but I also haven't done sftp 
> setup before, so I don't know for sure.
>
> Any help or insight would be greatly appreciated.
>
>

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