SOLVED (Partially):

Turns out  there were two issues here:

When generating the private key and csr with keytool or openssl - The .p12
did not have a nickname so when imported into the certutil database (via
pk12util) certutil would create a nickname using the text name of the
certificate. The solution was to add -n $NICKNAME to openssl pkcs12 command
used to create the .p12. 

When generating the private key & csr with certutil - The key is listed in
the certutil database as orphaned even after importing the signed
certificate. As a result even though the certificate had the right name it
was not associated with a key and couldn't be used. The behavior looked like
this old bug Windows certutil
(https://bugzilla.mozilla.org/show_bug.cgi/show_activity.cgi?id=452391) that
should have been fixed a while ago.





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