Offline Outlook Address Book – delays in syncing Outlook and Exchange 2010 – Solved!

When an administrator makes a change in Active Directory/Exchange, why do the changes not appear in the Outlook Offline Address Book immediately?

I found that it may take up to two days for the changes to appear in Outlook.

In Exchange 2010 it takes even longer to synchronize the changes in the OAB than Exchange 2007.  After the OAB is updated, which by default is once a day, it may take up to 8hrs for the OAB to be available to the client. The reason is that the OAB is generated in the MAILBOX role and needs to be copied to the CLIENT ACCESS role. The CLIENT ACCESS role checks for changes every 8 hrs. On top of these delays, if a client does not close/open his or her Outlook, it can take even longer for a change to take place.

If you want the changes to appear in your Outlook Address Book right away, you need to do the following:

  1. Make a change or changes to the OAB. An administrator can do this by going to their Exchange server, and open the Exchange Management Console. Drill down from Microsoft Exchange to ->Microsoft Exchange On-Premises ->Recipient Configuration -> Mailbox. Right-click on the user in which you want to make changes or add another SMTP address. Add or Edit the addresses, etc.EMC1
  2. Manually update OAB  in the Exchange server. Go to the Exchange Management Console -> Microsoft Exchange -> Microsoft Exchange On-Premises -> Organization Configuration -> Right-Click on Mailbox and choose Properties. Click on the Offline Address Book tab. Right-click on the default offline address book and choose Update. EMC2
  3. Restart Microsoft Exchange File Distribution service. On the Exchange server, go to Start -> Run -> type in Services.msc and hit Enter/OK. Browse to the Microsoft Exchange File Distribution service, right-click on the service and click Restart.Services
  4. You may need to Sync the Domain Controllers between sites (in a multi-site environment).
  5. Download the OAB in Outlook. Open Outlook on the client that wants the change. Go to the File tab/menu. Click on the Account Settings button and then click on Download Address Book…OutlookDownloadAddressBook

Otherwise, the process may take up to 56  hrs (24hrs to generate OAB, 8 hrs to update the CLIENT ACCESS, and 24 hrs to update Outlook).

Exchange/SBS 2003 – You do not have permission to send to this recipient. -Solved!

There are a lot of variables where a problem like this can take a while to track down and resolve, so hopefully if you encounter this issue again, the resolution will be easy.

A user called complaining they would receive a bounceback message from Exchange whenever trying to send an email as a different user, for example, “[email protected]”. They had not previously experienced this problem trying to send on behalf of that user and “something suddenly changed.”

To make a long story short, in this case, the resolution was that the From: field contained a corrupt .NK2/NickName entry for the “Promoter” address. When auto-resolving the email address for the “From” field, I had to type in the first letter of the bad entry, arrow down to the corrupt entry in the nickname list, so that it was highlighted and hit the Delete button. Next, to put in the correct “From: Promoter” address, I had to manually click the “From” button, go to the Global Address List and select “Promoter”. This resolved the correct entry and the From: field was now populated with “Promoter” instead of “[email protected]”. The message could now be sent without a failure/bounceback/error message.

Read below for the workflow that caused the problem and what I had to do to resolve it:

The user opened a new mail message. The From field is “shown” and the user typed in the first letter of the address who the email is from. In this case, “p”. This auto-resolved the nickname as an email address “[email protected]”. The user would then type in the recipients name into the To: field (in this case [email protected]) and then supply a subject, a message body, and hit send. A moment later the following email arrived from the Exchange System:

Your message did not reach some or all of the intended recipients.

Subject: test Sent: 4/27/2011 11:43 AM
The following recipient(s) cannot be reached:
example@hotmail.com on 4/27/2011 11:42 AM            You do not have permission to send to this recipient.  For assistance, contact your system administrator.            MSEXCH:MSExchangeIS:/DC=local/DC=domain:servername

Solution:

The first thing to check was that the user has the ability to send on behalf of the “Promoter” account:

On the SBS2003 server, go to Server Management. Click on the View menu and checkmark the “Advanced Features”. Then browse   -> Active Directory Users and Computers -> Domain.local ->MyBusiness ->Users -> SBSUsers

Right click on the account that the user is trying to send on behalf of (in this case “Promoter”). Click on the Exchange General tab. Click on the Delivery Options… button. Under Send on behalf, make sure the user that is trying to send as is listed under “Grant this permission to:”. If not, click the Add button… and add the user.

Next, in Server Management, browse to Advanced Management -> EXCHANGESERVERNAME (Exchange) ->Servers -> SERVERNAME -> Protocols -> SMTP

Right-click on “Default SMTP Virtual Server” and click Properties.

SMTP Properties.jpg
Click image to enlarge

Under the Access tab, click on the Relay… button

Under Relay Restrictions, “Only the list below” should be selected and Granted: the server’s IP address/SNM; and Granted loopback 127.0.0.1

Uncheck “Allow all computers which successfully authenticate to relay, regardless of the list above. Click on the Users… button. Under Permissions – Group or user names, make sure Authenticated Users has both Submit and Relay permission set to Allow. Click OK, OK, OK.

If any changes have been made to SMTP, right-click on Default SMTP Virtual Server under Protocols/SMTP and Stop/Start the Default SMTP Virtual Server.

Now, on the client, open a new mail message, remove the bad auto-resolving address, click on the From: button, select the account you wish to send from, and hit “Send”. See the 2nd paragraph of this post for further details on how to accomplish this part. The message should now be sent to the recipeint with the correct “From” address.

 

 

 

 

ActiveSynch troubleshooting on Exchange/SBS 2003

Do you have Exchange running in your environment but are having trouble connecting iPhones and Android phones? ActiveSync is much more preferable to POP or IMAP, so hunker down and fix ActiveSync on your server to get email, calendar, and contacts synched with your smartphones. Below are two of my favorite links for troubleshooting ActiveSync on Exchange and Small Business Server 2003. I was able to resolve issues on a few servers who’s certificates had expired by using the following resources:

Alan Hardisty’s ActiveSync Configuration Guide is a great starting point:

http://alanhardisty.wordpress.com/2010/02/28/exchange-2003-and-activesync-configuration-and-troubleshooting/

Secondly, the following website can test Exchange connectivity in a number of different ways:

https://testexchangeconnectivity.com/

The site above is able to test exchange connectivity with the following tests:

Microsoft Exchange ActiveSync Connectivity Tests
Microsoft Exchange Web Services Connectivity Tests
Microsoft Office Outlook Connectivity Tests
Internet E-Mail Tests

 

 

ActiveSynch troubleshooting on Exchange/SBS 2003

Do you have Exchange running in your environment but are having trouble connecting iPhones and Android phones? ActiveSync is much more preferable to POP or IMAP, so hunker down and fix ActiveSync on your server to get email, calendar, and contacts synched with your smartphones. Below are two of my favorite links for troubleshooting ActiveSync on Exchange and Small Business Server 2003. I was able to resolve issues on a few servers who’s certificates had expired by using the following resources:

Alan Hardisty’s ActiveSync Configuration Guide is a great starting point:

http://alanhardisty.wordpress.com/2010/02/28/exchange-2003-and-activesync-configuration-and-troubleshooting/

Secondly, the following website can test Exchange connectivity in a number of different ways:

https://testexchangeconnectivity.com/

The site above is able to test exchange connectivity with the following tests:

Microsoft Exchange ActiveSync Connectivity Tests
Microsoft Exchange Web Services Connectivity Tests
Microsoft Office Outlook Connectivity Tests
Internet E-Mail Tests