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Validation Error: SMTP Error: Could not connect to SMTP host.

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Microsoft is stopping to provide basic-auth with POP, IMAP and SMTP, customers must use OAUTH, could be this your problem? Or simply your server is deny any outbound connections with remote SMTP?

If you have SSH access to your server try with "telnet smtp.office365.com 587" and look for a reply/open port.

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