WebAdaptor certificate not recognized

For a dev environment, I created a fake Certificate Authority using OpenSSL.
I first generated a key and certificate PEM then used the files to export a PFX. I then created a server key and request file. I signed the request file with the CA -adding a config file with subject alternative names- that I had created and exported a PFX.

For the next steps I added the CA to my trusted root of CAs on windows, added the server PFX in IIS to my site, then bound port 443 to the certificate.
Despite this, I still get the error that the server could not prove its identity because of its name.

Am I missing something? Do I need to do use the same server certificate I created to replace the one by default in server admin?
Note that I am operating on a VM in Azure. I added localhost and the server hostname on Azure to the list of SAN.