Hi @hyphencoding - welcome to the Local Community! 
Thank you for bringing your question here.
When you’re using the font, are you using the full URL or just the relative URL?
(ie: example.com/heres-my-link versus /heres-my-link)
I’m wondering if you’re using the full URL and then with Live Links enabled it’s not seeing that file.
Let me know if that makes sense,
Sam 