Sending notifications via SMPT.OFFICE365.COM work with SSL enabled

We are trying to send e-mail notifications using Exchange Online. Everything I can find online shows that this uses smtp.office365.com. This works for us if we don't select the SSL check box in Mail Options, but when we select to use SSL, it fails.

This is what a packet capture looks like on the Adaxes server when attempting to use SSL, over port 587. It is clear here that Microsoft hits the point where it says it's ready to start mail negotiation, but then Adaxes just stops. Why is this?

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by (70 points)

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by (310k points)
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Hello,

The behavior is expected and it is Microsoft’s requirement that SSL is not used. In terms of Adaxes settings it means that the The server requires an encrypted connection (SSL) checkbox is cleared. It does not mean your mail will be sent unencrypted. If you specified a secure port (465 or 587), Adaxes will use TLS, which is effectively an upgraded version of SSL with fixed security vulnerabilities.

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