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GMail detects Rockstor as a 'Less Secure' application #1083
With the default setup Rockstor can't use GMail, login is not allowed.
This error turns you to this page: https://support.google.com/mail/answer/78754
After reading that I got to this support page: https://support.google.com/accounts/answer/6010255
Enabling the special gmail address for rockstor I made for 'Access for less secure apps' the issue was resolved and the test email now arrives.