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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

Reply
151 replies

Jan 18, 2011 5:13 AM in response to josephcorbett

This problem has been "mostly" resolved for me. However, it seems to still occur on occasion. Only now, it even occurs on iCal on desktops and other clients. It also seems to occur when a Time Machine backup is running on the server. If you get the error dialog and then wait a few moments, it will start working again with no effort. It's a little strange. This appears to affect more than just calDAV though.

Jan 23, 2011 7:56 AM in response to e.f.

Same problems as described (also with CardDAV). The problem for me only exists when working in 3G mode. With WiFi enabled there is no problem (tried with different 3g operators).


Strangely, When going to the iPhone's Settings (in 3g mode) >> Mail, Contacts, Calendars >> Cal/Card-DAV account: When I insert the right credentials it's verifying and leaves. Server log is showing normal data.

Later, When the login box shows and the correct credentials are typed in. The server log responds normal and accepts the credentials! even though the iPhone does not want to accept this.

I also tried to import the signed certificate with the "iPhone Configuration Utility" but had no luck so far...

Tried with a iPhone 2g 3.1.3 and there is no problem at all.

Feb 11, 2011 7:11 AM in response to racso-nl

hi folks

I applied the patch mentionned above a few months ago and it perfectly helped - Problem was gone (have around 10 usere connected to the server, all of them had the issue). Now about 2 weeks ago I installed 10.6.6 and bingo, the problem is back.... get password prompts again for CalDAV as well as for CardDAV on both iPhones as well as iPads. annoying.

I checked the settings in the plst, but they are now as they were before the update.

Anyone with similar issues or solutions?

Feb 15, 2011 11:20 AM in response to Mackeroni72

Anyone had any progress with this one? I get this on my iPad, and some users of the same CalDav calendar also get it. Seems to happen after an extended period of non-usage. I use my iPad for work pretty regularly, and usually need to re-enter the password every morning when I unlock the iPad.

Worse is that now this happens on my iPhone too! I am on a 3GS and had 3.1.2 - over the weekend I installed 4.2.1 and now get the same thing on my iPhone - only the interval is MORE frequent. Maybe after 1 or 2 hours if I don't use my phone I will be asked to re-enter my CalDav password.

Pretty annoying this one.

Mar 26, 2011 3:08 PM in response to e.f.

iOS 4.3.1 lists as a bug fix:

- Resolves an issue authenticating with some enterprise web services

Unfortunately the "enterprise web service" doesn't appear to be CalDAV, as I installed it and within hours I saw the password request popup as usual.

So, that's also a "still happening for me" too... Even with the very latest iOS version.

Apr 4, 2011 4:01 PM in response to e.f.

I am running Snow Leopard Server 10.6.7 with SSL enabled and iOS 4.3.1 on all my devices and experience this problem all the time. Wondering if Apple is aware of the problem and if it is being worked on? Perhaps one of the Apple moderators could chime in!? Any other fixes other than the one discussed? I don'd really want to revert to an outdated and less secure authentication method.

Apr 7, 2011 6:41 PM in response to jpawelchak

I am slowly being driven insane by this. I can't find any reason for this constant password nagging. It happens on all my iOS devices, CalDAV AND CardDAV now (that's a new torture).

How can a company that claims moral ownership over 'user experience' have such a shoddy and inconsistent implementation when it comes to THIER OWN groupware? This is an ALL APPLE ecosystem we are talking about here. How can they justify such poor interoperability between their own sets of products? If iCal Server can't be optimized for even the mobile devices in the same family with native support for CalDAV built in, well what's the point?

This is just one aggravation in Apple's string of leftover aggravations they are constantly creating by enforcing conformity to their ecosystem, constantly creating new technology avenues and restricting their environment to them, and then walking away from them without warning after their users have gone to great pains and expense in an effort to comply with their technology mandates. Apple makes my life as a sysadmin both a blessing and a curse, and lately I identify more and more with the later.

Anyone found anything new in their own examination of this issue yet?

Sorry for the rant, sometimes it's just gotta come out.

Apr 16, 2011 11:32 PM in response to e.f.

I am running Mac OS X Server 10.6.7 (10J869) on a Mac Mini and had the same problem for some time now. A couple of days ago I installed the latest security updates AND changed a setting for the web service (German):

Server-Admin, Web, Einstellungen, Allgemein, "Dauerhafte Verbindung trennen nach:" was 15 is now 150 seconds.

My English translation (it is the last entry on the page):

Server-Admin, Web, settings, general, "disconnect permanent connection after:" was 15 is now 150 seconds.


I have not seen the password prompt since... 🙂


Does it work for you? Any other ideas?

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

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