izenk opened a new issue #2625: Could not connect to SMTP host URL: https://github.com/apache/cloudstack/issues/2625 <!-- Verify first that your issue/request is not already reported on GitHub. Also test if the latest release and master branch are affected too. Always add information AFTER of these HTML comments, but no need to delete the comments. --> #### ISSUE TYPE <!-- Pick one below and delete the rest --> **Other** #### COMPONENT NAME <!-- Categorize the issue, e.g. API, VR, VPN, UI, etc. --> **Management Node** #### CLOUDSTACK VERSION <!-- New line separated list of affected versions, commit ID for issues on master branch. --> **4.11.0** #### CONFIGURATION <!-- Information about the configuration if relevant, e.g. basic network, advanced networking, etc. N/A otherwise --> * **Advanced Networking** * **KVM** #### OS / ENVIRONMENT <!-- Information about the environment if relevant, N/A otherwise --> **CentOS Linux release 7.4.1708** #### Summary Goal: integrate CloudStack with external SMTP relay. SMTP relay is Office365 relay from Office365 subscription. Parameters to connect: smtp.office365.com:587 In general there are two cases for secure connection: * SSL (First SSL handshake, then SMTP HELO) * TLS (First SMTP HELO, then STARTLS) CS does not allow to specify method to use and by default use SSL, what leads to errors: ~~~ 2018-04-25 13:32:59,733 ERROR [c.c.a.AlertManagerImpl] (Email-Alerts-Sender-1:null) (logid:) Failed to send email alert javax.mail.Mes sagingException: Could not connect to SMTP host: smtp.office365.com, port: 587; nested exception is: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection? ~~~
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