If your trying to restore to Outlook from the BB make sure the settings are correct. Normally when an appointment is made on the BB it flows to the Outlook Calendar either by direct sync or wireless. Check your options. Dont lose the backup.
When you installed the new OS it was clean so a sync with good data on the BB from a backup should work.
Try reading this for some additional info.
Overview
Wireless calendar synchronization occurs only one-way from the Microsoft® Outlook® calendar to the BlackBerry smartphone calendar. It does not synchronize from the BlackBerry smartphone to the Microsoft Outlook calendar.
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Cause
This issue may be caused by one of the following:
The BlackBerry Enterprise Server services are not running under the BlackBerry Enterprise Server service account.
The BlackBerry Enterprise Server service account does not have the appropriate permissions.
The Collaboration Data Object (CDO) is not present or supported with the Microsoft Exchange environment.
The BlackBerry Enterprise Server service account is a Domain Administrator.
The Microsoft Exchange Server's Public Folder database is not mounted.
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Resolution
Complete the appropriate resolution for your cause.
Cause 1
The BlackBerry Enterprise Server services are not running under the BlackBerry Enterprise Server service account.
Resolution 1
Verify that all BlackBerry Enterprise Server services are running under the appropriate BlackBerry Enterprise Server service account.
Note: Several BlackBerry Enterprise Server services run under the Local System account (for example, the BlackBerry Attachment Service or the BlackBerry MDS Services - Apache Tomcatxxx8482; Service).
To confirm that the correct account is specified, complete the following steps:
In Administrative Tools, select Services and double-click the BlackBerry Enterprise Server services.
From the Log On As tab, verify that the correct BlackBerry Enterprise Server service account name is specified.
If a different BlackBerry Enterprise Server service account name is specified, complete one of the following steps:
If the BlackBerry Enterprise Server was installed using the administrator account or another administrative account, switch the service account to the BlackBerry Enterprise Server service account. For instructions, see one of the following articles:
For BlackBerry Enterprise Server software version 3.6, see KB04334.
For BlackBerry Enterprise Server software versions 4.0 to 5.0, see KB04293.
OR
If the BlackBerry Enterprise Server was installed using the BlackBerry Enterprise Server service account, switch the service account to the one that corresponds to the BlackBerry Enterprise Server services.
Note: This occurs if a BlackBerry Enterprise Server service pack or hotfix was not installed using the BlackBerry Enterprise Server service account.
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Cause 2
The BlackBerry Enterprise Server service account does not have the appropriate permissions.
Resolution 2
To update BlackBerry smartphone users' mailboxes, the appropriate permissions are needed. Modify the BlackBerry Enterprise Server service account permissions by completing the following steps:
Microsoft Exchange Server 2000 and Microsoft Exchange Server 2003
In the Exchange System Manager, right-click the Exchange administrative group name and click Delegate Control.
Click Next, then click Add to open the Delegate Control window.
Click Browse to open the Select Users, Computers or Groups window, and select the new BlackBerry Enterprise Server service account.
From the Role drop-down list, select Exchange View Only Administrator and click OK.
Click Next, then click Finish.
Open Exchange System Manager, and go to Administrative Groups/First Administrative Group/Servers.
Right-click the Microsoft Exchange Server name, click Properties, then click the Security tab.
Verify the Allow inheritable permissions from parent to propagate to this object check box is selected.
Choose the service account name and select the appropriate check boxes to allow Administer information store,Receive As, and Send As permissions.
Verify that no denied permissions are selected for the BlackBerry Enterprise Server service account.
Click Apply, then click OK.
In Administrative Tools, select Active Directory Users and Computers.
Right-click the BlackBerry Enterprise Server service account, then click Properties.
On the Member of tab, verify that Domain Users is displayed in the list.
If the BlackBerry Enterprise Server is installed on a domain controller, verify that Administrators is listed.
Microsoft Exchange Server 5.5
In Exchange Administrator, enable the Service Account Admin permission for the new BlackBerry Enterprise Server service account in both the Site and Configuration containers.
For more information, see KB00886. For more information on setting permissions on Microsoft Exchange Server 5.5, visit the Microsoft Support web site.
Microsoft Exchange Server 2007
Open the Microsoft Exchange Shell by going to Start > Programs > Microsoft Exchange Server 2007 > Exchange Management Shell.
To set the Exchange View Only Administrator role, type the following command:
add-exchangeadministrator BESAdmin -role ViewOnlyAdmin
Where BESAdmin is the name of the BlackBerry Enterprise Server service account.
To check the Exchange View-Only Administrator role, type the following command:
get-exchangeadministrator | Format-List
The BlackBerry Enterprise Server service account should be displayed with a ViewOnlyAdmin role.
To set the Send As, Receive As, and Administer Information Store permissions, type the following command:
get-mailboxserver server_name | add-adpermission -user BESAdmin -accessrights GenericRead, GenericWrite -extendedrights Send-As, Receive-As, ms-Exch-Store-Admin
Where server_name is the name of the Microsoft Exchange Server 2007 or Microsoft Exchange Cluster, and BESAdmin is the name of the BlackBerry Enterprise Server service account.
To check the Send As, Receive As, and Administer Information Store permissions, type the following command:
get-mailboxserver server_name | get-ADpermission -user BESAdmin | Format-List
Where server_name is the name of the Microsoft Exchange Server 2007 or Microsoft Exchange Cluster and BESAdmin is the name of the BlackBerry Enterprise Server service account.
Important: Make sure that the BlackBerry Enterprise Server service account is not a member of any Microsoft® Active Directory® groups that have the required permissions denied. For more information, see KB04557.
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Cause 3
The Collaboration Data Object (CDO) is not present or supported with the Microsoft Exchange environment.
Resolution 3
Verify that the CDO.DLL file is supported with the Microsoft Exchange Server environment.
For Microsoft Exchange Server 2007 SP2
Verify Service Pack 1 for BlackBerry Enterprise Server 5.0 has been applied.
Verify Maintanence Release 1 for BlackBerry Enterprise Server 5.0.1 has been applied.
For Microsoft Exchange Server 2007 SP1 and below
Go to Control Panel - Add or remove programs on the BlackBerry Enterprise Server.
Verify that Messaging API and Collaboration Data Objects 1.2.1 is present.
If not present, download and install the Exchangemapicdo.exe 1.2.1 installer package from the Microsoft support site.
For Microsoft Exchange Server 2000 and Microsoft Exchange Server 2003
Go to the Exchsrvr\bin directory to check the version of the CDO.DLL file on your Microsoft Exchange Server.
Verify that the CDO.DLL file on the BlackBerry Enterprise Server is the same or later version of the CDO.DLL file on the Microsoft Exchange Server.
Note: If multiple versions of the CDO.DLL file exist, verify that all copies match.
At a command prompt, go to the directory where the CDO.DLL file is located.
Type regsvr32 cdo.dll, and press ENTER. A confirmation will display indicating that the file registered successfully.
For Microsoft Exchange 5.5
Go to the System32 directory to check the version of the CDO.DLL file on the Microsoft Exchange Server.
Verify that the CDO.DLL file on the BlackBerry Enterprise Server is the same or later version of the CDO.DLL file on the Microsoft Exchange Server.
Note: If multiple versions of the CDO.DLL file exist, verify that all copies match.
At a command prompt, go to the directory where the CDO.DLL file is located.
Type regsvr32 cdo.dll and press ENTER. A confirmation will display indicating that the file registered successfully.
Note: For information on how to obtain and apply the CDO.DLL file, see KB02937. To verify that the CDO.DLL file is registered, see KB04912.
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Cause 4
The BlackBerry Enterprise Server service account is a Domain Administrator.
Resolution 4
Verify that the BlackBerry Enterprise Server service account is not a Domain Administrator.
Note: If Domain Administrator is found under the member of tab, perform a switch BlackBerry Enterprise Server service accounts, see KB04293.
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Cause 5
The Microsoft Exchange Server's Public Folder database is not mounted.
Resolution 5
Mount the Public Folder database on the Microsoft Exchange Server.
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Additional Information
If the BlackBerry Enterprise Server service account is a member of any protected group such as the Domain Administrators or Enterprise Administrators groups, the Send As permission will be expressly denied from the exchange mail store. Without the Send As permission, the BlackBerry Enterprise Server will not be able to update the BlackBerry smartphone userxxx8217;s calendar on the Microsoft Exchange Server. Verify that the BlackBerry Enterprise Server service account does not inherit this role from Microsoft Active Directory groups, is not a member of any protected group, or does get any protected group inherited in the Exchange System Manager or Exchange Management Console.
See KB02466 for more information on one-way calendar synchronization when connected to BlackBerry Enterprise Server version 3.5.
See KB03784 for more information on the Windows Server® 2003 domain controller memory leak that affects wireless calendar synchronization.
Visit the Microsoft Support web site at
Microsoft Corporation for additional information on how to assign service account access to all mailboxes in Microsoft Exchange Server 2003.