Hello and thanks for your post here. I am sorry to hear you're having trouble connecting from Outlook after renewing your certificate. Can I have you try exporting the newly renewed certificate as a PFX file with a strong password, then update your port bindings with this file and password before retesting? If you continue to have trouble with this please submit a ticket with support and we'd be happy to investigate further.
Kyle Kerst
IT Coordinator
SmarterTools Inc.
www.smartertools.com