@PickleRick In case you are interested this is the only solution I found for my issue. So short story ... There is an issue with python3 that it can't/won't respect self signed certs, there is no workaround to make it recognize your CA. You can create a unique SSL context in each of the SSE config files that don't check SSL Steps: (reference:https://stackoverflow.com/questions/27835619/urllib-and-ssl-certificate-verify-failed-error?page=1&tab=scoredesc#tab-top) cd /opt/splunk/etc/apps/Splunk_Security_Essentials/bin grep -r "urlopen(request)" /opt/splunk/etc/apps/Splunk_Security_Essentials/bin In each config file that has a urlopen command you need to modify the following: At the top of the file: import ssl context = ssl._create_unverified_context() At each urlopen line (search in vi using /urlopen) add context=context like this: urlopen(request, context=context) Re-run the grep command to make sure you have modified everything. As you noted above with all these edits we won't be able to update SSE unless we then go through this process again after updating, but unless Python changes how they do SSL verification we don't really have a choice. Thanks again for your assistance in pointing me in the right direction.       ... View more