It may have downloaded outlook.office365.com's server certificate against a local .pem file and that could be the error.
If you did run this check with the --ssl-ca-file option, can you search for a file that may be called ca_file.pem and remove it?
Thanks
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That error you are seeing is from the latest version of the plugin, try and go back one version and see if that works for you.
Can you run this on the XI server to see if there any errors that could be helpful to trouble shoot this?