Hi Andrew,
To discard any “by default” problem:
If you click the gear icon > plugins > installed plugins (not gerar icon > plugins > find plugins) do you see your plugins?
Do you have the py-winrm node executor and Ansible plugin installed? these plugins are shown in the “gear icon > plugins > find plugins > “installed” tab by default.
Probably the functionality is working but the plugins aren’t installed/deleted.
Also, can you try without the following repo lines in your rundeck-config.properties file?
rundeck.repository.plugins.provider.1.type=file rundeck.repository.plugins.provider.1.path= rundeck.repository.plugins.provider.1.config.baseDir=/opt/rundeck/libext/Regards.