It looks like it has something to do with having no password for the
root user like on my dev box.

I have the same

        [ERROR] 1396  Operation ALTER USER failed for 'root'@'localhost'

in my error log and after every try a stale *.tmp file in /var/lib
/mysql-files.

The "ALTER user"  command comes from the file
 "/var/lib/dpkg/info/mysql-server-5.7.postinst"
You read in line 368:
"If there is no root password set we enable the auth_socket plugin for the root 
user."
This seems fails for some SSL related problems.

I could solve the block with these steps:

1. delete stale tmp files in /var/lib/mysql-files
2. Comment the line 370 which is :
echo "ALTER USER 'root'@'localhost' IDENTIFIED WITH 'auth_socket';"  >> 
"$initfile"

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https://bugs.launchpad.net/bugs/1817374

Title:
  mysql-server-5.7 5.7.25 upgrade did not complete properly

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