Gilles Gravier, as per Google
https://support.google.com/mail/troubleshooter/1668960?hl=en&from=75726&rd=1#ts=1665018,1665144
if port 465 doesn't work, then one would use 587 as an alternative.
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** Changed in: libreoffice (Ubuntu)
       Status: Expired => New

** Changed in: libreoffice (Ubuntu)
       Status: New => Invalid

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https://bugs.launchpad.net/bugs/1178248

Title:
  LO (4.0.3) hangs when testing mail merge settings in writer

Status in “libreoffice” package in Ubuntu:
  Invalid

Bug description:
  It hangs when I Launch Writer:
  - Tools->Options->LibreOffice Writer->Mail Merge E-mail
  - Fill in the details (I use Gmail's smtp.gmail.com, with SSL enabled
  and port 465).
  - Select Server Authentication, check "Server requires authentication".
  - Enter Username (@gmail.com address) and password.
  - Click OK.
  - Close the settings by clicking OK.
  - Open Tools->Options->LibreOffice Writer->Mail Merge E-mail
  - Check settings are properly memorized.
  - Click "Test settings"... and that hangs.

  WORKAROUND: If you change the port from 465 to 587 it works fine.

  ---
  ApportVersion: 2.0.1-0ubuntu17.2
  Architecture: i386
  DistroRelease: Ubuntu 12.04
  InstallationMedia: Ubuntu 12.04.2 LTS "Precise Pangolin" - Release i386 
(20130213)
  MarkForUpload: True
  Package: libreoffice 1:3.5.7-0ubuntu4
  PackageArchitecture: i386
  ProcEnviron:
   TERM=xterm
   PATH=(custom, no user)
   LANG=fr_FR.UTF-8
   SHELL=/bin/bash
  ProcVersionSignature: Ubuntu 3.5.0-28.48~precise1-generic 3.5.7.9
  Tags:  precise running-unity
  Uname: Linux 3.5.0-28-generic i686
  UpgradeStatus: No upgrade log present (probably fresh install)
  UserGroups: adm cdrom dip lpadmin plugdev sambashare sudo

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