Unable to Connect to Mail Server via Windows Mail

My YunoHost server

Hardware: VPS from SkySilk
YunoHost version:
I have access to my server : Through SSH & the Web Portal
Are you in a special context or did you perform some particular tweaking on your YunoHost instance ? : no
If yes, please explain: N/A

Description of my issue

When attempting to add my mail server to the Windows 10 Mail client, everything works and no connection issues are reported. I am able to receive emails normally, they appear fine. When sending, replying, or doing any other modification action on the client, the SMTP server cannot work and no specific error is provided. When using a localhost webmail client, it functions. On Outlook 365, it prompts for a valid certificate, as it’s currently self-generated.

To combat my certificate issue, I disabled CloudFlare’s routing and let it go directly to the machine. I then enabled Let’s Encrypt and it works. Once again, the system works I’m just unsure of why the connection fails. The firewall is open.

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