Hi Orin,
I have tested this in several versions of Thunderbird: 
52.9.1 (64-bit) 
57.0b2 (64-bit) 
60.0 (64-bit) 
I get the same result as you do.
I will report to Mozilla on this.
Thanks for detailing the steps.
:)
G

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

Title:
  Printing multiple messages to file, gets overwritten

Status in thunderbird package in Ubuntu:
  Confirmed

Bug description:
  Binary package hint: thunderbird

  When printing multiple messages (in one go) to a file, only the last
  message ends up in the file. Apparently the file gets overwritten for
  each message.

  I expected the file to contain all messages.

  To reproduce:
  1. Select multiple messages.
  2. File -> Print... , select Print To File. Printer "PostScript/default". 
Enter filename and click Print.
  3. View generated PostScript file (in Evince, for example) to see it only 
contains the last message.

  This on Ubuntu 9.10, Thunderbird version 2.0.0.23 (20090817).

  ProblemType: Bug
  Architecture: i386
  Date: Tue Jan 19 15:36:58 2010
  DistroRelease: Ubuntu 9.10
  InstallationMedia: Ubuntu 9.10 "Karmic Koala" - Release i386 (20091028.5)
  NonfreeKernelModules: nvidia
  Package: mozilla-thunderbird (not installed)
  ProcEnviron:
   LANG=en_US.UTF-8
   SHELL=/bin/bash
  ProcVersionSignature: Ubuntu 2.6.31-17.54-genUser Name
  SourcePackage: thunderbird
  Uname: Linux 2.6.31-17-generic i686
  --- 
  AddonCompatCheckDisabled: False
  ApportVersion: 2.20.7-0ubuntu3.9
  Architecture: amd64
  AudioDevicesInUse:
   USER        PID ACCESS COMMAND
   /dev/snd/controlC0:  eric       2196 F.... pulseaudio
  BuildID: 20180522092515
  Channel: Unavailable
  CurrentDesktop: ubuntu:GNOME
  DistroRelease: Ubuntu 17.10
  Extensions: extensions.sqlite corrupt or missing
  ForcedLayersAccel: False
  IfupdownConfig:
   # interfaces(5) file used by ifup(8) and ifdown(8)
   auto lo
   iface lo inet loopback
  IncompatibleExtensions: Unavailable (corrupt or non-existant 
compatibility.ini or extensions.sqlite)
  InstallationDate: Installed on 2017-06-04 (391 days ago)
  InstallationMedia: Ubuntu 17.04 "Zesty Zapus" - Release amd64 (20170412)
  IpRoute:
   default via 192.168.178.1 dev wlp14s0 proto static metric 600 
   169.254.0.0/16 dev wlp14s0 scope link metric 1000 
   192.168.178.0/24 dev wlp14s0 proto kernel scope link src 192.168.178.27 
metric 600
  Locales: extensions.sqlite corrupt or missing
  Package: thunderbird 1:52.8.0+build1-0ubuntu0.17.10.1
  PackageArchitecture: amd64
  PrefSources: prefs.js
  ProcVersionSignature: Ubuntu 4.13.0-45.50-generic 4.13.16
  Profiles: Profile0 (Default) - LastVersion=52.8.0/20180522092515 (In use)
  RunningIncompatibleAddons: False
  Tags:  artful wayland-session
  Themes: extensions.sqlite corrupt or missing
  Uname: Linux 4.13.0-45-generic x86_64
  UpgradeStatus: Upgraded to artful on 2018-01-06 (175 days ago)
  UserGroups: adm cdrom dip lpadmin plugdev sambashare sudo
  _MarkForUpload: True
  dmi.bios.date: 11/13/2012
  dmi.bios.vendor: Insyde Corp.
  dmi.bios.version: V2.13
  dmi.board.asset.tag: Type2 - Board Asset Tag
  dmi.board.name: VA70_HC
  dmi.board.vendor: Acer
  dmi.board.version: Type2 - Board Version
  dmi.chassis.type: 10
  dmi.chassis.vendor: Chassis Manufacturer
  dmi.chassis.version: Chassis Version
  dmi.modalias: 
dmi:bvnInsydeCorp.:bvrV2.13:bd11/13/2012:svnAcer:pnAspireV3-771:pvrV2.13:rvnAcer:rnVA70_HC:rvrType2-BoardVersion:cvnChassisManufacturer:ct10:cvrChassisVersion:
  dmi.product.family: Type1Family
  dmi.product.name: Aspire V3-771
  dmi.product.version: V2.13
  dmi.sys.vendor: Acer

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