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DiskCheckup only supports the most common form of SMTP authentication (AUTH LOGIN). There is no support for the more secure (AUTH CRAM-MD5) authentication or encryption. So if your SMTP server expects either of the two, DiskCheckup would be unable to send notification e-mails.
As a workaround, if your SMTP server maintains the previous session, you can try sending an e-mail from your mail client first (in order to authenticate), and then try sending the test e-mail again without authentication enabled (as the SMTP server has already authenticated).
I'm using version 3.1 build 1006 and I'm having the same issue. I've verified I can authenticate with other programs using AUTH LOGIN, however I still get authentication not supported in DiskCheckup.
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