Hi caitlinokane,
Thanks for your feedback. From the scree shot, I understand that you’re using Outlook on your Windows 8 machine. And when trying to set up the Office 365 account, an error “An encrypted connection to your mail services is not available” is reported.
This issue occurs if the Autodiscover CNAME record for your domain doesn’t exist or isn’t set up correctly. Autodiscover record lets Outlook clients connect to the cloud-based service by using the Autodiscover service. Therefore, Outlook profile settings can be configured automatically by simply entering the e-mail address and password.
I suggest you make sure that the Autodiscover CNAME record is created correctly for your email domain at your Domain Name System (DNS) host. You can refer to this article to resolve the connecting issue.
support.microsoft.com/.../2404385
Reference
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Autodiscover record
@Brian, thanks for your information.
Best regards,
Young Yang