Hi Orin,
I have Thunderbird 52.9.1 (64-bit) and I am on Ubuntu 18.04.

I tried the steps above but they are slightly different.

To reproduce:
1. Select multiple messages
2. Click on menu in the top right of the window 
3. Click Print... 
4. Select Print To File 
5. Select Postscript or PDF (no difference)
6. Enter filename  
7. Click the green "Print" button at top right of window


I have a different result than you do.
I selected three emails. The first gets printed to the file. The second and 
third get printed on the regular printer. No difference if Postscript or PDF is 
selected (both produce same result).

What version of Ubuntu and Thunderbird are you using?
Thanks
G

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https://bugs.launchpad.net/bugs/509665

Title:
  Printing multiple messages to file, gets overwritten

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