When I close Outlook, it crashes and detects the Kleopatra Plug-in as the reason. Sometimes, when starting Outlook, Kleopatra is not found and starting procedure stops. Reproducible: Always
There was bugfix for a nasty, random crash caused by GpgOL recently. This might be your Problem. https://bugs.gnupg.org/gnupg/issue1837 If you still experience Problems with Outlook / Kleopatra please report them at bugs.gnupg.org with the component GpgOL there.