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Recurring CalDAV login issues with iPhones and SLS (10.6 Server)

I have 10.6.4 Snow Leopard Server running on a Mac Mini and am having intermittent problems with various iPhones logging into CalDAV calendars. The iPhones are a 3G running iOS 3.1.3 and a 3GS running iOS 4.1.

iCal server works perfectly, with Push, on desktop clients.

The iPhones do work occasionally. Push is still not possible (AFAIK) but 15 minute fetch interval is acceptable for now (when is push coming to iPhones btw?). However, a few times per week, sometimes as many as 5 times in a single day, the iPhone will report "Password Incorrect." This happens on its on, presumably after one of the fetch intervals. Re-entering the password usually works, and is stored correctly for hours or days, but eventually it happens again. Sometimes password is accepted after re-entry but sync will silently stop working, which is even worse than the error popping up.

Each iPhone has 3 CalDAV accounts, one of which is a delegate, one of which is shared by all. The password issue happens with all of them, but far more often with the shared account. The password incorrect prompt does NOT always happen with all of them at once, sometimes just one of the accounts will throw the login error and the others will work for a while.

On the server, iCal has Authentication set to "any method", port 8008 and SSL on, Port 8443

The iPhones connect to CalDAV with SSL on port 8443 using "server" set to server.companyname.com

I have deleted the Calendar accounts on the phones repeatedly, hardware reset the phones, deleted all data and set up accounts again. This fixes the problem for a few days but then it comes back.

I don't see much in the iCal server logs, but I might not know what to look for. What should I look for or try next?

Thanks for any help.

Mac Mini 2Ghz Intel Core 2 Duo, 4GB RAM, Mac OS X (10.6.4)

Posted on Oct 13, 2010 12:58 PM

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151 replies

Dec 5, 2010 8:30 AM in response to Vermyndax

I'm not surprised by that. This problem used to be much worse for me, It would crop up on the desktop apps even mail.app would get hit with a random password authentication request, specifically when attempting to send an email. I'm not sure why my issue has been reduced to calendar on the iOS 4.2.1 but so far that is the only time I see it.

Things I have done that may have helped to improve the situation are...

- Running disk permission repair frequently
- Setting mail.app to only send from port 587
- blocking traffic to all unnecessary ports
- using SSL and blocking non- SSL ports (careful with blocking non SSL smtp ports you may inhibit outside emails from reaching your clients)

I think the snow leopard server team really focused on making an enterprise solution for closed networks, while implementing mobile access and of course supporting VPN to allow clients to access the corporate network externally. Thats pretty lame in my opinion because that type of setup is less desirable to smaller business that just want a mail/calendar/contact server. Oh well fingers crossed that an update will remedy the situation.

Ironically this could probably have been avoided if they had supported push for the iPhone. :-/

Dec 7, 2010 6:00 AM in response to Vermyndax

This is great! Although I feel a bit noobish about attempting this without asking for greater detail from all of you very capable administrators. Can someone break it down for me step by step? I even need the instructions on what app to run to mount the specific folder to edit the plist, admittedly I could not run this server if it was not for the extensive yet buggy GUI which is probably the source of this problem in the first place. Also once the plist has been edited I imagine making any changes to the calendar server using the admin console would not be recommended am I right?

Anyway if someone could lay it out for me in very basic steps me and my entire office would be tremendously grateful.

Recurring CalDAV login issues with iPhones and SLS (10.6 Server)

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