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I'm running an Mac OS X Server (10.6.7) with iCal, Address Book and Mail enabled. My issue is that the clients (iCal and Calendar in iOS) keeps asking for passwords on strange intervals, and it usually results in it not accepting the right password until you restart the client. It can run smoothly for days and some times it just goes completely bananas. It makes no difference if its a regular user or a Open Directory user.

This happens to all the services mentioned above but iCal is the worst.

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Is your OpenDirectory LDAP service running properly? What about Kereberos? – tegbains Jun 4 '11 at 16:34
Everything seems to be in order, not anomalies in the error logs. The kerberos log has this kinda of records: Jun 05 12:17:16 servername krb5kdc[73](info): got routing msg type 5(RTM_LOSING) v5 Jun 05 12:17:16 servername krb5kdc[73](debug): routing msg not interesting – Christoffer Winterkvist Jun 5 '11 at 10:17

This is a known issue. In my own testing, it appears to be fixed in Mac OS X Server v10.6.8. The release notes for the update mention:

Calendar Service
- Improves authentication support for iOS devices.

If this does not resolve your problem, then the workaround used until now was to edit /private/etc/caldavd/caldavd.plist to enable Basic authentication and disable Digest. Note that this is a bad idea if users communicate with the server over an untrusted network without SSL or VPN.

The same configuration changes can be applied to the Address Book service by editing /private/etc/carddavd/carddavd.plist. Look for Authentication / Basic / Enabled and change it to true, and Authentication / Digest / Enabled to false.

Again, do not use this workaround if the traffic is unencrypted. Without SSL or VPN the passwords are clearly visible to anyone monitoring the network.

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It still prompts me for passwords, not just as often. I hope iOS 5 will fix this, I believe the problems revolves around the clients and not the server. – Christoffer Winterkvist Jul 6 '11 at 8:29
This issue still persists in iOS5 and Lion. – Christoffer Winterkvist Oct 9 '11 at 10:57

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