For years I printed any type of document from my MacBook Pro running MacOS 10.13.6 to a LaserJet 5 with parallel connection installed on a Windows XP machine used solely as a print server. Never had a single failure until an electrical storm this spring with a nearby lightning strike fried that XP machine. It was a very good machine, state of the art at the time I built it, with Tyan 2x processor MB vintage 2001. Very sad that it died. Acquired a USB to parallel cable and connected the printer to a USB port on a hub connected to my Pro. Absolutely no problem to add and share printer in MacOS as generic PCL type. Here is USB definition of that printer:
MANUFACTURER:Hewlett-Packard;COMMAND SET:PJL,MLC,PCL,PCLXL;MODEL:HP LaserJet 5;CLASS:PRINTER;DESCRIPTION:Hewlett-Packard LaserJet 5
I can again print any file type from any application running in MacOS and/or Windows stuff in VirtualBox except PDF in Adobe reader. The only way I can print any PDF is to open the PDF file in Preview. If I try to print a PDF from Adobe the file fails to print usually with a "filter failed" notation in the error log. I can see the aborted file in the printer queue but nothing, and I mean nothing will get that file to print. The quene entry usually says something like "28% file prited," but the print function is completely stalled. On occassion (meaning not every time) the file actually will print when I restart the machine, as if MacOS recognized an unfinished task and restarted it. Why sometimes and not others is a mystery.
I have tried every remedy reported on the net; renove printer, reset printer system, restart machine, add new printer, again and again ad infinitum. I have invested many hours, at leasrt 25 researching and trying reported solutions, all for naught. I am a retired software engineer, 31 years experience, the last 5 with Google, so I can read English (Spanish and French too) and can follow instructions, but I conclude the Adobe print function in the MacOS version (11.0.23) is the squirriest piece of printer functionality ever written. My guess is the bits inside Reader cannot correctly convert PDF to PCL, thus the "filter failed" error message. But, all is not lost. Preview, written by, ..., drum role, Apple, can perform that conversion.
I doubt anything positive will come from this post, but I had to get my frustration off my chest.