# WinRM and Kerberos. WINRM CONNECTION ERROR: Bad HTTP response returned from server. Code 500 **URL:** \ **Category:** Get Help\ **Tags:** winrm, venv, windows, python, ubuntu\ **Created:** [November 14, 2024, 10:16am UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908 "2024-11-14T10:16:01Z")\ **Posts on this page:** 16\ **Page:** 1
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 14, 2024, 10:16am UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/1 "2024-11-14T10:16:01Z")
A few months ago, I was able to set up an ansible environment in a Virtual environment on a Ubuntu 24.04 server. I use it mainly to manage Windows Servers through WinRM with a kerberos authentication. I communicate on TCP/5985 port, and everything works fine. Lately, I tried to reproduce the same configuration. I mean setting up an ansible environment in a venv to manage Windows Servers. But it became **impossible** to properly communicate with Windows Servers using WinRM and kerberos. A simple win\_ping shows the error. On the working machine: ![image](https://us1.discourse-cdn.com/ansible/original/2X/6/6ac5f205c625387b9c8160fb5ef181e6db8acf83.png) On the latest ansible environment installed: ![image](https://us1.discourse-cdn.com/ansible/original/2X/0/0dd6c21b66e3bb14d6d73a1b5349b03408518465.png) If I execute the same thing in very verbose mode on both machines: ![image](https://us1.discourse-cdn.com/ansible/original/2X/f/f6a938dfd6c64b8f5036bc5fc1584998051d920c.png) ![image](https://us1.discourse-cdn.com/ansible/original/2X/8/8f6e330d4ec2a197af1cc8d1d33f98701ae8d962.png) ![image](https://us1.discourse-cdn.com/ansible/original/2X/4/4c2d9497af33410307e49e538d643038bdddbc29.png) In text mode, the full error message: > Citation > user@semaphoreui:~$ source ~/venv/ansible2.17\_python3.12/bin/activate;ansible -m win\_ping -i ~/windows\_hosts SERVER -k -vvvvvv;deactivate > ansible [core 2.18.0] > config file = None > configured module search path = [‘/home/user/.ansible/plugins/modules’, ‘/usr/share/ansible/plugins/modules’] > ansible python module location = /home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/ansible > ansible collection location = /home/user/.ansible/collections:/usr/share/ansible/collections > executable location = /home/user/venv/ansible2.17\_python3.12/bin/ansible > python version = 3.12.3 (main, Sep 11 2024, 14:17:37) [GCC 13.2.0] (/home/user/venv/ansible2.17\_python3.12/bin/python3.12) > jinja version = 3.1.4 > libyaml = True > No config file found; using defaults > SSH password: > setting up inventory plugins > Loading collection ansible.builtin from > host\_list declined parsing /home/user/windows\_hosts as it did not pass its verify\_file() method > script declined parsing /home/user/windows\_hosts as it did not pass its verify\_file() method > auto declined parsing /home/user/windows\_hosts as it did not pass its verify\_file() method > Parsed /home/user/windows\_hosts inventory source with ini plugin > redirecting (type: modules) ansible.builtin.win\_ping to ansible.windows.win\_ping > Loading collection ansible.windows from /home/user/.ansible/collections/ansible\_collections/ansible/windows > Loading callback plugin minimal of type stdout, v2.0 from /home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/ansible/plugins/callback/minimal.py > Attempting to use ‘default’ callback. > Skipping callback ‘default’, as we already have a stdout callback. > Attempting to use ‘junit’ callback. > Attempting to use ‘minimal’ callback. > Skipping callback ‘minimal’, as we already have a stdout callback. > Attempting to use ‘oneline’ callback. > Skipping callback ‘oneline’, as we already have a stdout callback. > Attempting to use ‘tree’ callback. > redirecting (type: modules) ansible.builtin.win\_ping to ansible.windows.win\_ping > redirecting (type: modules) ansible.builtin.win\_ping to ansible.windows.win\_ping > Using module file /home/user/.ansible/collections/ansible\_collections/ansible/windows/plugins/modules/win\_ping.ps1 > Pipelining is enabled. > \<[SERVER.ENTERPRISE.COM](http://SERVER.ENTERPRISE.COM)\> ESTABLISH WINRM CONNECTION FOR USER: [THE-WINUSER@ENTERPRISE.COM](mailto:THE-WINUSER@ENTERPRISE.COM) on PORT 5985 TO [SERVER.ENTERPRISE.COM](http://SERVER.ENTERPRISE.COM) > creating Kerberos CC at /tmp/tmpfeohiy61 > calling kinit with subprocess for principal [THE-WINUSER@ENTERPRISE.COM](mailto:THE-WINUSER@ENTERPRISE.COM) > kinit succeeded for principal [THE-WINUSER@ENTERPRISE.COM](mailto:THE-WINUSER@ENTERPRISE.COM) > \<[SERVER.ENTERPRISE.COM](http://SERVER.ENTERPRISE.COM)\> WINRM CONNECT: transport=kerberos endpoint=[http://SERVER.ENTERPRISE.COM:5985/wsman](http://SERVER.ENTERPRISE.COM:5985/wsman) > \<[SERVER.ENTERPRISE.COM](http://SERVER.ENTERPRISE.COM)\> WINRM CONNECTION ERROR: Bad HTTP response returned from server. Code 500 > Traceback (most recent call last): > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 268, in send\_message > root = ET.fromstring(ex.response\_text) > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ > File “/usr/lib/python3.12/xml/etree/ElementTree.py”, line 1336, in XML > return parser.close() > ^^^^^^^^^^^^^^ > xml.etree.ElementTree.ParseError: no element found: line 1, column 0 During handling of the above exception, another exception occurred: Traceback (most recent call last): File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/ansible/plugins/connection/winrm.py”, line 483, in \_winrm\_connect self.shell\_id = protocol.open\_shell(codepage=65001) # UTF-8 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 193, in open\_shell res = self.send\_message(xmltodict.unparse(req)) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 271, in send\_message raise ex File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 263, in send\_message resp = self.transport.send\_message(message) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/transport.py”, line 336, in send\_message response = self.\_send\_message\_request(session, prepared\_request) ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/transport.py”, line 352, in \_send\_message\_request raise WinRMTransportError(“http”, ex.response.status\_code, response\_text.decode()) winrm.exceptions.WinRMTransportError: Bad HTTP response returned from server. Code 500 SERVER | UNREACHABLE! =\> { “changed”: false, “msg”: “kerberos: Bad HTTP response returned from server. Code 500”, “unreachable”: true } Here is the environment details on the running machine: > Distributor ID: Ubuntu > Description: Ubuntu 24.04.1 LTS > Release: 24.04 > Codename: noble > pip freeze > ansible-core==2.17.3 > certifi==2024.8.30 > cffi==1.17.0 > charset-normalizer==3.3.2 > cryptography==43.0.0 > decorator==5.1.1 > gssapi==1.8.3 > idna==3.8 > Jinja2==3.1.4 > jmespath==1.0.1 > kerberos==1.3.1 > krb5==0.6.0 > MarkupSafe==2.1.5 > packaging==24.1 > pycparser==2.22 > pykerberos==1.2.4 > pyspnego==0.11.1 > pywinrm==0.5.0 > PyYAML==6.0.2 > requests==2.32.3 > requests-kerberos==0.15.0 > requests\_ntlm==1.3.0 > resolvelib==1.0.1 > urllib3==2.2.2 > xmltodict==0.13.0 > Collection Version > ansible.posix 1.5.4 > ansible.utils 5.1.1 > ansible.windows 2.4.0 > chocolatey.chocolatey 1.5.1 > community.crypto 2.21.1 > community.dns 3.0.2 > community.general 9.1.0 > community.library\_inventory\_filtering\_v1 1.0.1 > community.mysql 3.10.3 > community.vmware 4.5.0 > community.windows 2.2.0 > microsoft.ad 1.6.0 > vmware.vmware 1.3.0 On the **non-working** machines, I’ve tried to install exactly the same pip packages’ version or the latest version. Whatever I try, I always get this: > kerberos: Bad HTTP response returned from server. Code 500 error message. As we can see, the WinRM connection is clearly established: > ESTABLISH WINRM CONNECTION FOR USER: [USER@ENTERPRISE.COM](mailto:USER@ENTERPRISE.COM) on PORT 5985 TO [SERVER.ENTERPRISE.COM](http://SERVER.ENTERPRISE.COM) > creating Kerberos CC at /tmp/tmpfeohiy61 and the kerberos authentication is OK: > calling kinit with subprocess for principal [USER@ENTERPRISE.COM](mailto:USER@ENTERPRISE.COM) > kinit succeeded for principal [USER@ENTERPRISE.COM](mailto:USER@ENTERPRISE.COM) > \<[SERVER.ENTERPRISE.COM](http://SERVER.ENTERPRISE.COM)\> WINRM CONNECT: transport=kerberos endpoint=[http://SERVER.ENTERPRISE.COM:5985/wsman](http://SERVER.ENTERPRISE.COM:5985/wsman) And then: > \<[SERVER.ENTERPRISE.COM](http://SERVER.ENTERPRISE.COM)\> WINRM CONNECTION ERROR: Bad HTTP response returned from server. Code 500 > Traceback (most recent call last): > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 268, in send\_message > root = ET.fromstring(ex.response\_text) > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ > File “/usr/lib/python3.12/xml/etree/ElementTree.py”, line 1336, in XML > return parser.close() > ^^^^^^^^^^^^^^ > xml.etree.ElementTree.ParseError: no element found: line 1, column 0 > During handling of the above exception, another exception occurred: > Traceback (most recent call last): > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/ansible/plugins/connection/winrm.py”, line 483, in \_winrm\_connect > self.shell\_id = protocol.open\_shell(codepage=65001) # UTF-8 > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 193, in open\_shell > res = self.send\_message(xmltodict.unparse(req)) > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 271, in send\_message > raise ex > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/protocol.py”, line 263, in send\_message > resp = self.transport.send\_message(message) > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/transport.py”, line 336, in send\_message > response = self.\_send\_message\_request(session, prepared\_request) > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ > File “/home/user/venv/ansible2.17\_python3.12/lib/python3.12/site-packages/winrm/transport.py”, line 352, in \_send\_message\_request > raise WinRMTransportError(“http”, ex.response.status\_code, response\_text.decode()) > winrm.exceptions.WinRMTransportError: Bad HTTP response returned from server. Code 500 > SERVER | UNREACHABLE! =\> { > “changed”: false, > “msg”: “kerberos: Bad HTTP response returned from server. Code 500”, > “unreachable”: true > } I’ve tried many things, and I do know how to fix this very annoying issue. I really need you **help**. ---
**Author:** ![motorbass](https://avatars.discourse-cdn.com/v4/letter/m/13edae/32.png) [@motorbass](https://forum.ansible.com/u/motorbass)\ **Post date:** [November 14, 2024, 1:01pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/2 "2024-11-14T13:01:08Z")
> [@Iwan](#): > > Bad HTTP response returned from server. Code 500 Hi 🙂 For testing purpose, are you able to allow unencrypted connection with something like this : ```auto Set-Item -Path WSMan:\localhost\Service\AllowUnencrypted -Value true ``` And then re-run your playbook to check if it behaves the same or not. (my idea is to check if your venv and collections may be impacted by this setting) ---
**Author:** ![anon81884396](https://avatars.discourse-cdn.com/v4/letter/a/b782af/32.png) [@anon81884396](https://forum.ansible.com/u/anon81884396)\ **Post date:** [November 14, 2024, 1:11pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/3 "2024-11-14T13:11:26Z")
Working with Kerberos in Linux is extremely frustrating and the error messages are rarely useful. I feel your pain, man. I encountered this relatively recently and my issue was that I had one too many “kerberos”-related pip packages installed and it somehow lead to winrm connectivity not working. My currently working requirements.txt is ```auto ansible==8.7.0 ansible-runner==2.4.0 pywinrm==0.4.3 pywinrm[kerberos] receptorctl ``` I can’t account for why it used to work for you but no longer does, but it’s worth a shot. ---
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 14, 2024, 1:20pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/4 "2024-11-14T13:20:31Z")
> [@motorbass](#): > > `AllowUnencrypted` Before changing anything: ![image](https://us1.discourse-cdn.com/ansible/original/2X/b/bd4e5f46d4305b2b3d9d8dcfb0f51e9ece0fbca8.png) Then: ![image](https://us1.discourse-cdn.com/ansible/original/2X/4/42d09031a1bd17b7a05aa3db29ec3b6652486e39.png) Indeed, it seems the encryption is clearly the issue: ![image](https://us1.discourse-cdn.com/ansible/original/2X/b/b718a56f7a370bcdcee917fe63e2e109f8c2c78c.png) As I want to keep everything encrypted, I restore the encryption: ![image](https://us1.discourse-cdn.com/ansible/original/2X/b/bcb08f8cfb591419cf97974d968683f279fa6c6c.png) So I retry the win\_ping on the server that does not support the encryption: ![image](https://us1.discourse-cdn.com/ansible/original/2X/f/f8be30a990e072f3bbc0c650a0621234f7cc1555.png) My questions: - As I do not want to allow unencrypted transaction on thousands of servers, how can I fix this issue ? - Why the server installed and configured a few months ago has no issues with encryption ? Anyway, thank you for your help @motorbass ---
**Author:** ![motorbass](https://avatars.discourse-cdn.com/v4/letter/m/13edae/32.png) [@motorbass](https://forum.ansible.com/u/motorbass)\ **Post date:** [November 14, 2024, 1:23pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/5 "2024-11-14T13:23:01Z")
In addition to your test, @Iwan could you share your vars.yml or vars statement that configure ansible winRM settings please ? ---
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 14, 2024, 1:31pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/6 "2024-11-14T13:31:39Z")
For testing purposes, I’m using a simple hosts file: ![image](https://us1.discourse-cdn.com/ansible/original/2X/8/8a8226d471b507c5bbf23a6fb673ee0b783306d9.png) ![image](https://us1.discourse-cdn.com/ansible/original/2X/a/abdfa0ac04778deda0e3719898cdf7afef4da2dd.png) ---
**Author:** ![motorbass](https://avatars.discourse-cdn.com/v4/letter/m/13edae/32.png) [@motorbass](https://forum.ansible.com/u/motorbass)\ **Post date:** [November 14, 2024, 1:32pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/7 "2024-11-14T13:32:48Z")
Ok i was 99% sure you were using 5985. 5985 is for HTTP (so unencrypted) and 5986 is for HTTPS (so encrypted communication) Could you give a try using `ansible_port=5986` ? ---
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 14, 2024, 1:44pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/8 "2024-11-14T13:44:24Z")
The WinRM remains with the default configuration and listens on port 5985 only. ![image](https://us1.discourse-cdn.com/ansible/original/2X/5/50f0594868e8107a82c2d2363586970ef7edac29.png) so: ![image](https://us1.discourse-cdn.com/ansible/original/2X/8/83cf10d9a28d98a443ffd02e540aebcaf967203c.png) My historic server works without any issue on port 5985 and mandatory encryption. ---
**Author:** ![mariolenz](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/mariolenz/32/108_2.png) [@mariolenz](https://forum.ansible.com/u/mariolenz)\ **Post date:** [November 14, 2024, 1:59pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/9 "2024-11-14T13:59:48Z")
Why did you add the `vmware` tag? This doesn’t look like a VMware related issue at all, or am I wrong? ---
**Author:** ![motorbass](https://avatars.discourse-cdn.com/v4/letter/m/13edae/32.png) [@motorbass](https://forum.ansible.com/u/motorbass)\ **Post date:** [November 14, 2024, 2:01pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/10 "2024-11-14T14:01:36Z")
Ok, so as Microsoft said “_AllowUnencrypted : Allows the client computer to request unencrypted traffic_” so in our case, client requests only encrypted traffic. So probably the error code 500 means : the windows target received the request but doesn’t process it well and/or ansible doesn’t understand it as it should. So probably we should have a look at the Ansible venv. I had a look to my windows vars for winrm, could you give a try using only : ```auto ansible_connection: winrm ansible_port: 5985 ansible_winrm_transport: kerberos ``` Depending on the result we’ll have a look to the ansible collection version, pip version, pip collections version. ---
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 14, 2024, 2:33pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/11 "2024-11-14T14:33:50Z")
Indeed, it is clearly a mistake. It is not VMware related. ---
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 14, 2024, 3:39pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/13 "2024-11-14T15:39:03Z")
As requested: ![image](https://us1.discourse-cdn.com/ansible/original/2X/d/dbf367cfe9ba11918bd48b15dd5d84feefcdf0b8.png) It is still not working ---
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 14, 2024, 4:23pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/14 "2024-11-14T16:23:35Z")
On the running server: > ansible-core 2.17.3 > certifi 2024.8.30 > cffi 1.17.0 > charset-normalizer 3.3.2 > cryptography 43.0.0 > decorator 5.1.1 > gssapi 1.8.3 > idna 3.8 > Jinja2 3.1.4 > jmespath 1.0.1 > kerberos 1.3.1 > krb5 0.6.0 > MarkupSafe 2.1.5 > packaging 24.1 > pip 24.2 > pycparser 2.22 > pykerberos 1.2.4 > pyspnego 0.11.1 > pywinrm 0.5.0 > PyYAML 6.0.2 > requests 2.32.3 > requests-kerberos 0.15.0 > requests\_ntlm 1.3.0 > resolvelib 1.0.1 > urllib3 2.2.2 > xmltodict 0.13.0 On the NOT running server: > ansible-core 2.18.0 > certifi 2024.8.30 > cffi 1.17.1 > charset-normalizer 3.4.0 > cryptography 43.0.3 > decorator 5.1.1 > gssapi 1.9.0 > idna 3.10 > Jinja2 3.1.4 > kerberos 1.3.1 > krb5 0.7.0 > MarkupSafe 3.0.2 > packaging 24.2 > pip 24.3.1 > pycparser 2.22 > pyspnego 0.11.2 > pywinrm 0.5.0 > PyYAML 6.0.2 > requests 2.32.3 > requests-kerberos 0.15.0 > requests\_ntlm 1.3.0 > resolvelib 1.0.1 > urllib3 2.2.3 > xmltodict 0.14.2 Not so different. I’ve tried to install the pip packages from a ‘pip freeze’ on the running server, and install the very same version on the newly created server. It did not fix the issue… My questions: - Can it be related to the gcc version ? Some packages are built, and on the running server, they were built in July. - Should I try to reinstall everything on an Ubuntu 22.04 so the GCC version is older ? - Any other idea ? Suggestion ? ---
**Author:** ![jborean](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/jborean/32/1525_2.png) [@jborean](https://forum.ansible.com/u/jborean)\ **Post date:** [November 14, 2024, 10:04pm UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/15 "2024-11-14T22:04:04Z")
I see you have both kerberos and pykerberos installed. Both of these packages use the same Python namespace `kerberos` but the `kerberos` package does not have the extra bits to enable message encryption. Uninstall both `kerberos` and `pykerberos` if they are present and just do `pip install pywinrm[kerberos]`. By mixing and matching you are disabling message encryption over HTTP causing the connection to fail. ---
**Author:** ![Iwan](https://sea1.discourse-cdn.com/ansible/user_avatar/forum.ansible.com/iwan/32/5429_2.png) [@Iwan](https://forum.ansible.com/u/Iwan)\ **Post date:** [November 15, 2024, 8:28am UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/16 "2024-11-15T08:28:55Z")
> [@jborean](#): > > pywinrm[kerberos] Big big thank you ! Here’d what I did: Before uninstalling anything ![image](https://us1.discourse-cdn.com/ansible/original/2X/2/2ffdb237de1ddb89faf18697bcdabbf3a26673ee.png) What i executed: - pip uninstall kerberos pywinrm - pip uninstall requests\_ntlm and then: - pip install pywinrm[kerberos] ![image](https://us1.discourse-cdn.com/ansible/original/2X/1/108c50112b9a901fa5cd1ad9c1a37f4ecf098e32.png) And the final result: ![image](https://us1.discourse-cdn.com/ansible/original/2X/f/fb7477d6e4abe68c2825372e1e97ed826150ea3d.png) You made my day ! Thank you again ! 👍 ---
**Author:** ![system](https://us1.discourse-cdn.com/ansible/original/1X/1882d9a01da5d8996a862359b0913cc568a39b84.svg) [@system](https://forum.ansible.com/u/system)\ **Post date:** [December 15, 2024, 8:29am UTC](https://forum.ansible.com/t/winrm-and-kerberos-winrm-connection-error-bad-http-response-returned-from-server-code-500/10908/17 "2024-12-15T08:29:47Z")
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