Thanks for the info, Matt.

I've tried a number of versions of OpenSSL without any luck:

macOS El Capitan (where I originally had this problem) has Python 2.7.10 
with OpenSSL 0.9.8zh
FreeBSD 11.0-RELEASE has Python 2.7.12 with OpenSSL 1.0.2j
FreeBSD 11.0-RELEASE with manual build of Python 2.7 (latest) with manual 
build of OpenSSL 1.1.0b


On Thursday, October 13, 2016 at 12:53:02 PM UTC-5, Matt Davis wrote:
> Every case I've seen of this issue has come down to a problem deep in an 
> SSL/TLS implementation that causes the tunnel to get wedged. I've not dug 
> in far enough with the packet sniffer/TLS debugging to be sure which side 
> is the problem (Windows SChannel or OpenSSL), but on the machines I've seen 
> it on, it's 100% reproducible. There's not really anything we can do about 
> it at the Ansible level, as it's many dependencies away from us 
> (Ansible->pywinrm->requests->urllib3->pyopenssl->OpenSSL). 
> The only way I've been able to correct the problem on machines I've seen 
> it on is by recompiling Python against a newer OpenSSL build. Switching up 
> allowed ciphers on the Windows or OpenSSL side generally seems to just move 
> the problem around (ie, it fails in a different place but still quite 
> predictably). Switching to HTTP instead of HTTPS also makes the problem go 
> away, but, well, don't do that. Hoping to get some of the message-level 
> HTTP encryption stuff going in pywinrm soon (at least for Kerberos, and 
> jborean93 has done it for CredSSP), which could be another way to make this 
> go away in the future.
> -Matt
> On Thursday, October 13, 2016 at 8:10:34 AM UTC-7, Peter Rebholz wrote:
>> I'm also running into this issue and spent some time troubleshooting. In 
>> my case, the host I'm pushing the file to is on a separate network without 
>> incoming access to where we host the files, thus the proposed workaround of 
>> using `get_url` does not work.
>> In my troubleshooting, I've found out the following details:
>> 1. The timeout used by `pywinrm` is not relevant because the files are 
>> transferred via many small requests. You can play with this setting by 
>> defining the vars: `ansible_winrm_read_timeout_sec` and 
>> `ansible_winrm_operation_timeout_sec`. While the timeout was reflected in 
>> the error message, it had no effect.
>> 2. The temp file created by the `win_copy` always tops out at the same 
>> size: 110,840 KB
>> 3. The `winrm` connector uses 250,000 byte chunks to transfer the file. 
>> If you change the `buffer_size` parameter in 
>> `ansible/plugins/connection/` to something larger, then the temp 
>> file on the windows size will be larger than the 110,840 KB mentioned 
>> previously
>> 4. If you bump that `buffer_size` up enough, you can successfully 
>> transfer the whole file.
>> 5. By running the following command, I've always received the result 
>> "457" when the process fails, regardless of `buffer_size`. This seems to 
>> indicate that there is some bound that is being exceeded but I have not 
>> been able to figure out if it's a problem with ansible code or the WinRM 
>> service configuration on the server.
>>     ansible-playbook -vvvvv -l windows -i inventory playbook.yml | grep 
>> "WINRM PUT" | wc -l
>> That's as far as I've gone... Hopefully someone more familiar with the 
>> WinRM connector may have some ideas...
>> Peter
>> On Wednesday, August 31, 2016 at 9:21:36 AM UTC-5, Justin Dugan wrote:
>>> I am using this in the playbook:
>>> - name: copy {{eap_dir}}
>>>   win_copy: src="{{eap_dir}}" dest="c:/temp/{{eap_dir}}"
>>> And it's failing with:
>>> TASK [win_JBoss : copy] 
>>> ************************************
>>>  [WARNING]: FATAL ERROR DURING FILE TRANSFER: Traceback (most recent 
>>> call last):   File
>>> "/usr/lib/python2.7/site-packages/ansible/plugins/connection/", 
>>> line 204, in _winrm_exec
>>> self._winrm_send_input(self.protocol, self.shell_id, command_id, data, 
>>> eof=is_last)   File
>>> "/usr/lib/python2.7/site-packages/ansible/plugins/connection/", 
>>> line 185, in
>>> _winrm_send_input     rs = protocol.send_message(xmltodict.unparse(rq)) 
>>>   File "/usr/lib/python2.7
>>> /site-packages/winrm/", line 207, in send_message     return
>>> self.transport.send_message(message)   File 
>>> "/usr/lib/python2.7/site-packages/winrm/",
>>> line 173, in send_message     response = 
>>> self.session.send(prepared_request,
>>> timeout=self.read_timeout_sec)   File 
>>> "/usr/lib/python2.7/site-packages/requests/", line
>>> 596, in send     r = adapter.send(request, **kwargs)   File 
>>> "/usr/lib/python2.7/site-
>>> packages/requests/", line 499, in send     raise 
>>> ReadTimeout(e, request=request)
>>> ReadTimeout: HTTPSConnectionPool(host='host', port=5986): Read timed
>>> out. (read timeout=30)
>>> fatal: [jcinstalltest]: FAILED! => {"failed": true, "msg": "winrm 
>>> send_input failed"}
>>> Is there any way to adjust the timeout? This file is ~200Mb. I also have 
>>> a patch to copy which is ~400Mb so 30 seconds is probably too short.
>>> Thanks,
>>> Justin

You received this message because you are subscribed to the Google Groups 
"Ansible Project" group.
To unsubscribe from this group and stop receiving emails from it, send an email 
To post to this group, send email to
To view this discussion on the web visit
For more options, visit

Reply via email to