In the situation where you create a virtual printer from scratch, you can find that your printer settings you supplied are not correct. In this case, when printing from Windows, the print job will error, and in the Print Queue you'll see an 'Error - Printing' message.
Inspecting the event viewer logs doesn't yield any actionable errors.
If the error is due to something which can be fixed by the developer, for example, a missing or miss-configured printer setting or capability in the virtual printer, it would be useful to log this somewhere. Even if it's a verbose logging setting that needs to be turned on manually.
Alternatively, documenting the required settings for different virtual printer scenarios could be useful too.
For example, 'A virtual printer accepting PDF requires these settings...'.
Thanks!