> On Nov 19, 2016, at 7:04 PM, Ian Baker <idba...@gmail.com> wrote:
> 
> Hello,
> 
> We’re using CalendarServer via macOS Server.app v5.2.
> 
> Unfortunately, we’re having problems with calendar event invitations sent to 
> external users via email.  We have the com.apple.calendarserver user 
> configured in the Calendar preferences, but when the outbound invitation mail 
> is sent, the log reports authentication issues. There is a mismatch between 
> the password configured for the com.apple.calendarserver system user, and 
> that entered in the Server.app preferences.
> 
> How does one modify the password for the com.apple.calendarserver system 
> user, so that we can coordinate the two?


There are two keychain items in play here.  One is labeled 
“com.apple.servermgr_calendar" and it always stores the local 
com.apple.calendarserver account password.  The other is labeled 
“icalserver.invitations” and it stores the password for whatever IMAP/SMTP 
account(s) you are using.  Normally that account is also 
com.apple.calendarserver, but it may be different if the admin has chosen to 
use an external mail service.

So you want to open the Keychain Access app and find the 
com.apple.servermgr_calendar item.  It should contain the 
com.apple.calendarserver password.  Copy that password and paste it into 
Server.app’s “Edit invitation settings” dialog, thereby updating 
“icalserver.invitations” item.

If things are really out of sync and the com.apple.servermgr_calendar keychain 
item password does not match the com.apple.calendarserver user’s actual 
password (because perhaps someone changed it), you can delete that 
com.apple.servermgr_calendar keychain item, and then stop/start the calendar 
service — it will detect the missing keychain item, generate a new random 
password, assign it to the user and stick it in the 
com.apple.servermgr_calendar keychain item.  It would be up to you to then copy 
that into the Edit invitation settings.

Hope that helps,
~morgen

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