I'm having problems using secure SMTP in Microsoft Outlook
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If you are trying to send mail securely and you are using Microsoft Outlook you should be aware that Outlook defaults back to port 25 when trying to send securely, no matter what port you have specified. This is incorrect behaviour, other mail clients such as Thunderbird will default to the correct secured SMTP port (465).
We recommend you use Thunderbird if this is an issue for you.