Exchange Offline Address book Sync Issues

I have added an A record.
I had a look at the link you provided and just feel confused, we don't make use of the Public Folder so I'm assuming the OAB is web based.

I ran the Remote Connectivity Analyzer for Autodiscover and it failed

Please make sure your autodiscover working properly.  You can test autodiscover through "www.exchangetestconnectivity.com".


Please refer below link this might be help u out.

http://support.microsoft.com/kb/939765

http://social.technet.microsoft.com/Forums/exchange/en-US/d5673421-f1db-49c6-8e71-d6ccdc2a5369/offline-address-book-downloads-failed-during-a-manual-sendreceive-operation-witherror-0x8004010f

http://technet.microsoft.com/en-us/library/cc411331(v=exchg.80).aspx


http://blogs.technet.com/b/exchange/archive/2007/04/19/3401966.aspx

http://www.fixkar.com/articles/kb/1156/

What is the failure error mentioned?

Try all your required autodiscovertest
https://www.testexchangeconnectivity.com

The results of the autodiscover test

The Microsoft Connectivity Analyzer is attempting to test Autodiscover for djmohr@domain.co.za.
 Testing Autodiscover failed.
 
Test Steps
 
Attempting each method of contacting the Autodiscover service.
 The Autodiscover service couldn't be contacted successfully by any method.
 
Test Steps
 
Attempting to test potential Autodiscover URL https://domain.co.za/AutoDiscover/AutoDiscover.xml
 Testing of this potential Autodiscover URL failed.
 
Test Steps
 
Attempting to resolve the host name domain.co.za in DNS.
 The host name couldn't be resolved.
  Tell me more about this issue and how to resolve it
 
Additional Details
 Host domain.co.za couldn't be resolved in DNS InfoNoRecords.




Attempting to test potential Autodiscover URL https://autodiscover.domain.co.za/AutoDiscover/AutoDiscover.xml
 Testing of this potential Autodiscover URL failed.
 
Test Steps
 
Attempting to resolve the host name autodiscover.domain.co.za in DNS.
 The host name couldn't be resolved.
  Tell me more about this issue and how to resolve it
 
Additional Details
 Host autodiscover.domain.co.za couldn't be resolved in DNS InfoDomainNonexistent.




Attempting to contact the Autodiscover service using the HTTP redirect method.
 The attempt to contact Autodiscover using the HTTP Redirect method failed.
 
Test Steps
 
Attempting to resolve the host name autodiscover.domain.co.za in DNS.
 The host name couldn't be resolved.
  Tell me more about this issue and how to resolve it
 
Additional Details
 Host autodiscover.domain.co.za couldn't be resolved in DNS InfoDomainNonexistent.




Attempting to contact the Autodiscover service using the DNS SRV redirect method.
 The Microsoft Connectivity Analyzer failed to contact the Autodiscover service using the DNS SRV redirect method.
 
Test Steps
 
Attempting to locate SRV record _autodiscover._tcp.domain.co.za in DNS.
 The Autodiscover SRV record wasn't found in DNS.
  Tell me more about this issue and how to resolve it

As per the above seems your DNS name not resolving to the correct address

You please check whether it is working from inside network by typing the address
 https://autodiscover.internaldomain.com/AutoDiscover/AutoDiscover.xml
and check what is the response

Response from inside the network

<?xml version="1.0" encoding="UTF-8"?>
-<Autodiscover xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006">-<Response>-<Error Id="1548190240" Time="12:30:39.5805893"><ErrorCode>600</ErrorCode><Message>Invalid Request</Message><DebugData/></Error></Response></Autodiscover>

Did u get a password prompt?

Yes I did

ok good.

Did you enable web based distribution of OAB
Check the attachment

and try accessing OAB manually as well
https://exchangeservername.internaldomainname.com/OAB/OABGUID/oab.xml
OABerror.docx

I'm sure I did, how can I double check?

I followed the link, it prompts for username and password but then I get:

404 - File or directory not found.

The resource you are looking for might have been removed, had its name changed, or is temporarily unavailable.

Try only this and check whether it  returns
It should return something like this "The web server is configured to not list ....."
https://autodiscover.domain.com/OAB

It returns with "This page can't be displayed"

Seems your OAB directory has some issue in IIS

Forgot to ask one thing
Did you assign OAB to the Mailbox Databases?

And do this also create an A record "autodiscover" in your external DNS which points to your exchange public IP

Please check this also
https://www.experts-exchange.com/questions/26729667/How-to-recreate-OAB-virtual-directory-in-Exchange-2010-Server-2008-R2.html

Well I didn't specifically assign it to any other mailbox so I suppose it is assigned to the default one.

I will contact my ISP regarding the external DNS

Assign the mail store an OAB either through the EMC:
Organization Configuration-->Mailbox-->Database Management-->Properties on your Mailbox database/s-->Client Settings-->Offline address book
click Browse and select your addressbook

Or EMS
Get-MailboxDatabase | Set-Mailboxdatabase -offlineAddressBook "\Default Offline Address Book"

I have done that.

Did you try downloading OAB after configuring that?

Well nothing was changed, the OAB was assigned to the Mailbox that I use

Did u check the URL I posted in post#39479429 ?

No, I missed that, will have a look.

Just a question, if my autodiscover is not working would my OAB still work?

https://www.experts-exchange.com/questions/26729667/How-to-recreate-OAB-virtual-directory-in-Exchange-2010-Server-2008-R2.html

@ abbasiftt

I followed the link above and recreated the OAB will monitor and report back.

This is still a problem :(

Please make sure autodiscover is working
Try from outlook itself

is there a guide line to get autodiscover reconfigured?

Yea I looked at those links and had no luck.

So Autodiscover is not working and will not resolve?  You have a DNS record pointing to the exchange server correct?  Did you also check above on the web.config file in my earlier post?

When you open outlook there is a outlook icon in the system tray.  Do a ctrl + right-click on the outlook icon and choose connectivity test, test autodiscover and report back the results

I am trying to remove and recreate the Autodiscover Virtual directory and am running into a strange error

[PS] C:\Windows\system32>Remove-AutodiscoverVirtualDirectory -Identity MAILSRV\autodiscover
The operation couldn't be performed because object 'MAILSRV\autodiscover' couldn't be found on 'PDC.domain.za'.
    + CategoryInfo          : NotSpecified: (0:Int32) [Remove-AutodiscoverVirtualDirectory], ManagementObjectNotFoundE
   xception
    + FullyQualifiedErrorId : 986A88B,Microsoft.Exchange.Management.SystemConfigurationTasks.RemoveAutodiscoverVirtual
   Directory

For some reason Exch Management Shell is looking at my PDC and not the excahnge server.

@ NRhode

Yes the DNS entry is there. I looked for the web.config and it is not present.

The connectivity test fails

For the above you are using the exchange powershell correct?

Thats right

Try using the GUI to reset the Autodiscover VD:  http://www.exchangeitpro.com/2013/04/24/reset-exchange-2010-virtual-directories-via-gui/

Ok that did the trick, autodiscover VD has now been recreated

Ran the connectivity test again from Outlook and the Autodiscover still fails

Post the results :)

Looking for the reason of failure

Results attached

As for that error it is not detecting autodiscover.  Verify your autodiscover URLs and make sure you also have an internal & external DNS record pointing to the exchange server.

Can you ping autodiscover.domain.co.za and it sends a reply from exchange?

For autodiscover VD what is the URL?  is autodiscover also in your SSL cert?

Understanding and Troubleshooting AutoDiscover:  http://www.petri.co.il/autodiscover-configuration-exchange-2010.htm

To check the URL on the VD:  http://www.msexchange.org/blogs/walther/news/exchange-20072010-autodiscover-virtual-directory-urls-should-i-care-595.html

I can ping autodiscover.domain.za but not autodiscover.domain.co.za from inside the network. I am still waiting on my ISP to create a cname for autodiscover.domain.co.za.

The autodiscover.domain.co.za is present in my SSL cert.

I went through those links and these are the results:

[PS] C:\Windows\system32>Get-ClientAccessServer |fl


RunspaceId                           : ae63fe39-8cf2-4c9e-a48b-96a6ecacf62f
Name                                 : MAILSRV
Fqdn                                 : MAILSRV.domain.za
OutlookAnywhereEnabled               : True
AutoDiscoverServiceCN                : MAILSRV
AutoDiscoverServiceClassName         : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri       : https://mail.domain.co.za/autodiscover/autodiscover.xml
AutoDiscoverServiceGuid              : 77378f46-2c66-4aa9-a6a6-3e7a48b19596
AutoDiscoverSiteScope                : {Mail}
AlternateServiceAccountConfiguration :
IrmLogEnabled                        : True
IrmLogMaxAge                         : 30.00:00:00
IrmLogMaxDirectorySize               : 250 MB (262,144,000 bytes)
IrmLogMaxFileSize                    : 10 MB (10,485,760 bytes)
IrmLogPath                           : E:\Program Files\Microsoft\Exchange Server\V14\Logging\IRMLogs
IsOutOfService                       : False
MigrationLogLoggingLevel             : Information
MigrationLogFilePath                 :
MigrationLogMaxAge                   : 180.00:00:00
MigrationLogMaxDirectorySize         : 10 GB (10,737,418,240 bytes)
MigrationLogMaxFileSize              : 100 MB (104,857,600 bytes)
IsValid                              : True
ExchangeVersion                      : 0.1 (8.0.535.0)
DistinguishedName                    : CN=MAILSRV,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=domain,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=domain,DC=za
Identity                             : MAILSRV
Guid                                 : cb716ffa-d393-4a5a-958f-36a5b9fdb859
ObjectCategory                       : domain.za/Configuration/Schema/ms-Exch-Exchange-Server
ObjectClass                          : {top, server, msExchExchangeServer}
WhenChanged                          : 2013/09/09 07:48:29 PM
WhenCreated                          : 2013/01/30 07:54:26 AM
WhenChangedUTC                       : 2013/09/09 05:48:29 PM
WhenCreatedUTC                       : 2013/01/30 05:54:26 AM
OrganizationId                       :
OriginatingServer                    : PDC.domain.za

[PS] C:\Windows\system32>Get-AutodiscoverVirtualDirectory "MAILSRV\*" |fl


RunspaceId                      : ae63fe39-8cf2-4c9e-a48b-96a6ecacf62f
Name                            : Autodiscover (Default Web Site)
InternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated}
ExternalAuthenticationMethods   : {Basic, Ntlm, WindowsIntegrated}
LiveIdSpNegoAuthentication      : False
WSSecurityAuthentication        : False
LiveIdBasicAuthentication       : False
BasicAuthentication             : True
DigestAuthentication            : False
WindowsAuthentication           : True
MetabasePath                    : IIS://MAILSRV.domain.za/W3SVC/1/ROOT/Autodiscover
Path                            : E:\Program Files\Microsoft\Exchange Server\V14\ClientAccess\Autodiscover
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
Server                          : MAILSRV
InternalUrl                     :
ExternalUrl                     :
AdminDisplayName                :
ExchangeVersion                 : 0.10 (14.0.100.0)
DistinguishedName               : CN=Autodiscover (Default Web Site),CN=HTTP,CN=Protocols,CN=MAILSRV,CN=Servers,CN=Exch
                                  ange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=domain,CN=Mic
                                  rosoft Exchange,CN=Services,CN=Configuration,DC=csmeng,DC=za
Identity                        : MAILSRV\Autodiscover (Default Web Site)
Guid                            : 2b974ee1-c70e-41fd-8ec3-00f779844c45
ObjectCategory                  : domain.za/Configuration/Schema/ms-Exch-Auto-Discover-Virtual-Directory
ObjectClass                     : {top, msExchVirtualDirectory, msExchAutoDiscoverVirtualDirectory}
WhenChanged                     : 2013/09/11 04:42:14 PM
WhenCreated                     : 2013/09/11 04:42:14 PM
WhenChangedUTC                  : 2013/09/11 02:42:14 PM
WhenCreatedUTC                  : 2013/09/11 02:42:14 PM
OrganizationId                  :
OriginatingServer               : PDC.domain.za
IsValid                         : True

Are the InternalUrl and ExternalUrl supposed to be blank in the last output?

Create a new zone in your DNS server named "domain.co.za"
then create an A record "autodiscover" in the newly created zone and try

ok I did that and can now ping both autodiscover.domain.za and autodiscover.domain.co.za from inside the network

I followed the following link now as well

How to configure and verify Autodiscover for Exchange 2007 and 2010

Is it working now that autodiscover url is resolving with creating the new zone?  do another autodiscover test

Results of last autodiscover test

What is the results pain show?

The results pane

Something else that has popped up now since the autodiscover was fixed, some of my remote users are complaining that they have to enter their username and password serveral times before outlook connects to the Exchange.

I guess you know the format to enter username and password.

username:  domain\username
password: <password>

Yes I do, it's very strange as the first password prompt does connect it to the Exchange then it prompts for the password an addition 2 or 3 times.

Check if they have saved passwords in their credential manager.  Make sure they flushed their DNS to make sure their records are correct.

Also if you wanted to eliminate that domain\username for OWA etc you can change that by opening EMC > Server configuration > Client Access > Outlook Web Access tab > right-click and go to properties on owa > Authentication > Use forms-based authentication > Change the format to what you want

I checked the credential manager and the login details are present, but outlook still prompts for a username and password about 4 times after the first login attempt. Flushed DNS but no change.

Thanks gents problem is resolved