I’ve inherited an old Mac mini that used to be running a circa March 2016 
version of CalendarServer on it as a manually process launched from the bin/run 
-n script.  In the spirit of transparency, I set this up for the original user, 
wrote up instructions on how to start things, and haven’t really touched it 
since. 

The Mac mini has since been upgraded from macOS 10.11 directly to 10.14 Mojave, 
and to no one’s huge surprise, the CalendarServer will not start up, throwing a 
bunch of python-related errors.  After consulting with the owner, it was 
decided that the easiest thing to do would be to just install a new version and 
go from there.

I downloaded the latest 9.0 branch 
https://github.com/apple/ccs-calendarserver/archive/CalendarServer-9.0.tar.gz 
to a temp working directory and ran the develop script to download all the 
dependencies, which appears to have worked.  When I start the server using run 
-n though, I see the usual quick popup that asks if I want to allow python to 
receive incoming connections, which I click, but then things fail anyway saying 
that a connection to the database could not be established.

Log files are as follows:

=================
MiniMe:ccs-calendarserver-CalendarServer-9.0 julian$ ./bin/run -n
Using 
/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/.develop/virtualenv/bin/python
 as Python
Keychain already unlocked

Starting server...
:0: UserWarning: Your version of pyOpenSSL, 0.0, is out of date.  Please 
upgrade to at least 0.12 and install service_identity from 
<https://pypi.python.org/pypi/service_identity>.  Without the service_identity 
module and a recent enough pyOpenSSL to support it, Twisted can perform only 
rudimentary TLS client hostname verification.  Many valid certificate/hostname 
mappings may be rejected.
Reading configuration from file: 
/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/conf/caldavd-dev.plist
2018-12-09T19:42:29-0600 [-] Log opened.
2018-12-09T19:42:29-0600 [-] twistd 15.4.0 
(/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/.develop/virtualenv/bin/python
 2.7.10) starting up.
2018-12-09T19:42:29-0600 [-] reactor class: 
twisted.internet.selectreactor.SelectReactor.
2018-12-09T19:42:29-0600 [-] AMPPushNotifierFactory starting on 62311
2018-12-09T19:42:29-0600 [-] ControlSocket starting on 
'./data/Logs/state/caldavd.sock'
2018-12-09T19:42:29-0600 [txdav.base.datastore.subpostgres#info] Cluster 
already exists at 
/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/data/Data/Database/cluster
2018-12-09T19:42:29-0600 [txdav.base.datastore.subpostgres#info] Requesting 
postgres start via: 
['/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/.develop/roots/PostgreSQL/bin/pg_ctl',
 'start', 
'--log=/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/data/Logs/postgres.log',
 '--timeout=86400', '-w', '-o', "-c listen_addresses='' -c 
unix_socket_directories=/tmp/ccs_postgres_a9d519e9bbd00110455cda2e11f25c15 -c 
shared_buffers=79 -c max_connections=53 -c standard_conforming_strings=on -c 
unix_socket_permissions=0770 -c log_line_prefix=%t"]
2018-12-09T19:42:29-0600 [memcached-Default] [warn] kq_init: detected broken 
kqueue; not using.: Undefined error: 0
2018-12-09T19:42:29-0600 [memcached-Default] [warn] kq_init: detected broken 
kqueue; not using.: Undefined error: 0
2018-12-09T19:42:29-0600 [memcached-Default] [warn] kq_init: detected broken 
kqueue; not using.: Undefined error: 0
2018-12-09T19:42:29-0600 [memcached-Default] [warn] kq_init: detected broken 
kqueue; not using.: Undefined error: 0
2018-12-09T19:42:29-0600 [memcached-Default] [warn] kq_init: detected broken 
kqueue; not using.: Undefined error: 0
2018-12-09T19:42:29-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info] waiting for server to 
start....
2018-12-09T19:42:30-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info]  done
2018-12-09T19:42:30-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info] server started
2018-12-09T19:42:30-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info] pg_ctl process ended 
with status=0
2018-12-09T19:42:30-0600 [txdav.base.datastore.subpostgres#info] 
/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/.develop/roots/PostgreSQL/bin/pg_ctl
 exited
2018-12-09T19:42:31-0600 [txdav.base.datastore.subpostgres#critical] Can't 
start or connect to postgres: 'twistedcaldav.directory.augment.AugmentXMLDB'
2018-12-09T19:42:31-0600 [txdav.base.datastore.subpostgres#info] Requesting 
postgres stop via: 
['/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/.develop/roots/PostgreSQL/bin/pg_ctl',
 'stop', 
'--log=/Users/julian/Downloads/ccs-calendarserver-CalendarServer-9.0/data/Logs/postgres.log']
2018-12-09T19:42:31-0600 [memcached-Default] Signal handled: Terminated: 15.
2018-12-09T19:42:31-0600 [-] (UNIX Port ./data/Logs/state/caldavd.sock Closed)
2018-12-09T19:42:31-0600 [-] (TCP Port 62311 Closed)
2018-12-09T19:42:31-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info] waiting for server to 
shut down....
2018-12-09T19:42:32-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info]  done
2018-12-09T19:42:32-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info] server stopped
2018-12-09T19:42:32-0600 
[txdav.base.datastore.subpostgres.PostgresMonitor#info] pg_ctl process ended 
with status=0
2018-12-09T19:42:32-0600 [-] Main loop terminated.
2018-12-09T19:42:32-0600 [-] Server Shut Down.
============

Any word of advice?  I looked in this mailing list archive and the list of 
issues on github, but no one seems to have documented this issue yet.

Thanks!

-- 
Julian Y. Koh

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