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It seems that https can not be configured using the configuration file as described in http://wiki.eclipse.org/Orion/Server_admin_guide#Server_configuration_file. So far we can configure it only via properties in $ws/.metadata/.plugins/org.eclipse.core.runtime/.settings/org.eclipse.orion.server.configurator.prefs.
Szymon already figured this out, but making a note here so we don't lose track: This doesn't work because the code in ConfiguratorActivator#start doesn't consult the default preference scope. It accesses the instance scope directly, so it doesn't find the default values in the server config file.
Fixed with 9bd0aa59819bc4e14ba42f0f9820add05b3b7bb2 and 0cf1023b7491be5e1b1c263af77b389465efc608.