Hi @gongomgra thanks for the reply again,
I was able to fix this issue, I think your first reply was correct, that this was more so a Canvas problem.
I read the production start guide provided by Instructure and it mentions that there is an optional file domain that can be set in the domain.yml located at
The issue I was having was that I was using the Azure VM's DNS name for both the
Firstly I had to make two subdomains so for
example.com, I used
canvas.example.com as the domain and for the files domain I used
Thanks for the help, I hope this helps people in the future.