Using Different Versions of Microsoft Outlook for Manager/Delegate Pairs

Using different versions of Microsoft Outlook for manager/delegate pairs

Date published: November 2009

Summary: The purpose of this white paper is to discuss issues related to running different versions of Microsoft Outlook for manager/delegate pairs (for example, Microsoft Office Outlook 2003 and Microsoft Office Outlook 2007). The paper provides a statement from the Microsoft Outlook product team on the issue, and discusses general issues, customer-reported issues, and calendar risk areas for this scenario. The information contained in this document represents the current view of Microsoft Corporation on the issues discussed as of the date of publication. Because Microsoft must respond to changing market conditions, it should not be interpreted to be a commitment on the part of Microsoft, and Microsoft cannot guarantee the accuracy of any information presented after the date of publication.

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All other trademarks are property of their respective owners. Table of Contents

OFFICIAL STATEMENT FROM THE OUTLOOK PRODUCT TEAM 4

ABOUT THIS DOCUMENT 4

GENERAL INFORMATION 5 Make delegate changes from Outlook 2003 only 5 Use the most current builds 6 Calendar feature differences 6 Performance/caching issues 6 Inability to send meeting updates 7 “Sniffer” feature 7 Client-side logging 7 Informational updates 7 Conflict resolution 8

CUSTOMER-REPORTED ISSUES 8 Private item handling 8 Printing daily calendars 8 Attendee updates 8 Free/busy issues 8

GENERAL CALENDAR RISK AREAS 9 Missing/duplicate meetings 9 Troubleshooting challenges 9 Sync software integration 9

SUMMARY 9 Official Statement from the Outlook Product Team The text in the Microsoft Knowledge Base (KB) article (http://support.microsoft.com/kb/924470) is written specifically to discourage long-term cross-version solutions. For example, setting up an organizational unit of delegates on Microsoft Office Outlook 2003, and then upgrading the rest of the company including managers to Microsoft Office Outlook 2007 is discouraged. When planning to run for long periods of time with mixed versions of Outlook accessing the same Microsoft Exchange mailboxes (as in the manager/delegate scenario), customers can report inconsistencies. To minimize these inconsistencies, upgrading manager/delegate pairs together where possible is recommended. Unfortunately, the cause of these inconsistencies has proven to be extremely difficult to track down. They are often complex timing issues related to being temporarily offline, using various devices to update calendars, using add-in solutions on mixed versions of Outlook, and subtle differences between the code of Outlook 2003 and Outlook 2007. Combining all of these update semantics together and aiming them at important mailboxes like manager/delegate mailboxes can, from time to time, result in calendar inconsistencies. The Microsoft Office Outlook product team is aware of this, and has worked very hard for the Outlook 2007 Service Pack 2 (SP2) release to dramatically reduce these inconsistencies. The calendar reliability work incorporated into the SP2 release was the result of many man-years of work. Unfortunately, the code base between 2007 and 2003 is too different to take these calendar reliability fixes back to 2003, and would require significant re-engineering and risk. The best way to get the improvements of the calendar reliability in Outlook 2007 SP2 is to run Outlook 2007 SP2. Microsoft understands that corporate environments cannot be upgraded overnight. Many of our customers will run with mixed versions for extended periods of time during upgrades. This is a normal upgrade process, and in no way is the product team saying that an upgrade cannot be performed without simultaneously upgrading all manager/delegate pairs in a single sweep. However, targeting manager/delegate pairs to be upgraded in close proximity will reduce the possibility of encountering calendar inconsistencies. Should you run into inconsistencies during your upgrade, usually the simplest way to address them is to upgrade both manager and delegate to the same Outlook version. Investigating the inconsistencies with mixed versions is often a time-consuming and somewhat painful experience for our customers. Where upgrading will nearly always resolve the issue faster, we have found with experience that an issue that is resolved significantly faster is often favored by our customers.

About this document This document focuses on the scenario of upgrading a manager to Outlook 2007 while the delegate remains on Outlook 2003. If the delegates are upgraded to Outlook 2007 and the manager remains at Outlook 2003, there is a benefit that the delegate uses all the improvements for Outlook 2007 that are covered in the following sections. However, this still remains an untested scenario. The document is divided into three main sections:  General information. This section provides best practices and information about how some product changes can affect the delegate behavior.

 Customer-reported issues. This section lists some reported customer issues, their symptoms, and recommendations for handling those issues.

 General calendar risk areas. This section lists some general calendar areas that are historically involved in calendar issues and troubleshooting. This section is not specific to mixed manager/delegate pairs, but it will be important to distinguish between issues that arise from mixed versions, and ones that arise independent of version. As the product team statement confirms, the mixed version scenarios were not designed and tested during the development cycle, so this is not a complete issues list. It is a general document to help the internal support teams understand the area and the factors that might lead to problems.

General information The following are general recommendations for this manager/delegate pair scenario. Make delegate changes from Outlook 2003 only Outlook stores some delegate settings in a property in the manager’s mailbox. This property name changed from Outlook 2003 to Outlook 2007. Outlook 2007 knows how to read and use the settings written by Outlook 2003, but Outlook 2003 does not know how to read and use settings created by Outlook 2007. Therefore, it is important to make all delegate additions/removals from an Outlook 2003 client. Symptoms would include the inability to see private items (more details follow), and the free/busy publishing interval not being honored. For example, suppose the manager has specified that 6 months of free/busy should be published for their calendar, and you find that only 3 months are being published by the delegate. The first troubleshooting step for the helpdesk should be to reset the delegates by using an Outlook 2003 client. During the initial upgrade of a manager from Outlook 2003 to Outlook 2007, the delegate settings WILL be migrated. Only new or additional delegate changes that happen AFTER the migration would need to be made from an Outlook 2003 client. If the manager is running Outlook 2003 and the delegates are using Outlook 2007, this should not be a problem. Use the most current builds Within the mixed version scenarios, it is important that the version of Outlook 2003 and Outlook 2007 be up-to-date to ensure the best possible results. For example:  Outlook 2003 SP2 introduced a new architecture for how meetings transition from the tentative to the accepted state. This new architecture is used in Outlook 2007 as well, so having the manager and delegate use this same algorithm “under the hood” keeps things much more consistent. This change is documented in the following KB article:  894470 A meeting is removed from your Outlook Calendar after you accept the meeting and then delete the accepted meeting request (http://support.microsoft.com/default.aspx? scid=kb;EN-US;894470)  The “send on behalf” ability is stored as a property on the user in Active Directory. To change this property, you must have a writable Global Catalog (GC) server when adding delegates normally. With the latest versions of Outlook 2003 and Outlook 2007, the ability to add delegates even when a writable GC is not available has been added. This change is documented in the following KB article:  946208 Error message when you try to add a delegate in Outlook 2003: "The Delegates settings were not saved correctly" (http://support.microsoft.com/default.aspx?scid=kb;EN- US;946208)

 Sent and Deleted Item behaviors are controllable with the latest builds of each version. You can specify which mailbox (manager or delegate) to which the sent items and deleted items from the manager mailbox are moved. This change is documented in the following KB article:  972148 When you send an e-mail message from a shared mailbox in Outlook 2007, the sent message is not saved in the Sent Items folder of the shared mailbox (http://support.microsoft.com/default.aspx?scid=kb;EN-US;972148)  Calendar improvements have been made incrementally in practically every service pack and cumulative update that has been released for Outlook 2007, so for each version, you should strive to have the latest public builds. This change is documented in the following KB article:  968009 Outlook 2007 improvements in the February 2009 cumulative update (http://support.microsoft.com/default.aspx?scid=kb;EN-US;968009)  The current “latest builds” are available from the How to obtain the latest Office cumulative update section of the following KB article:  953878 Cumulative updates are available from the Microsoft Office team to fix reported problems (http://support.microsoft.com/default.aspx?scid=kb;EN-US;953878) Calendar feature differences The following are key calendar issues for this manager/delegate pair scenario. Performance/caching issues By default in Outlook 2007, shared calendars are cached in the .ost file. If you are a delegate using Outlook 2003, you will always be using the online version of the manager’s calendar. This results in different experiences for the delegate. For example, if the network is slow, an Outlook 2003 delegate will suffer the slowness, whereas an Outlook 2007 delegate will be working from the .ost and not experience the network delays. Inability to send meeting updates When you make a change to a meeting and try to send an update, Outlook purposefully checks to see if any changes have been made to the item by another person/process. Consider this scenario: 1. You open a meeting titled “Business Review” and change the time from 12 to 1.

2. You leave the meeting open while you take a coffee break.

3. The manager of the meeting opens the meeting and changes the attendee list.

4. You come back from the break, and send the update.

At this point you WANT Outlook to check whether the item has changed “underneath” you to ensure you do not lose the new attendee data. In Outlook 2003, several design limitations, and especially the interaction of managed code add-ins can create scenarios where this test fails. Outlook mistakenly thinks that the item has changed “underneath” you when it fact it has not. So when you try to send an update, even when nothing has changed, you are presented with an error. The solution is to close and restart Outlook, and then create and send the update again. Outlook 2007 SP2 introduced a new architecture that almost entirely removes this potential issue when running in Cached Mode. This change is documented in the following KB article:  968009 Outlook 2007 improvements in the February 2009 cumulative update (http://support.microsoft.com/default.aspx?scid=kb;EN-US;968009) “Sniffer” feature The “sniffer” feature is the part of Outlook that finds a meeting request in your Inbox and creates a tentative meeting in your calendar. In Outlook 2003, this is implemented in a way that is much more prone to “interruptions.” For example, you can have a meeting request in your Inbox, and it does not show in the manager’s calendar even after an hour of idle time. In Outlook 2007, the “sniffer” feature is implemented in a new way that makes it more robust and performs better, and these sniffer problems are much less likely. Outlook 2007 also extends the sniffer functionality so that it “sniffs” meeting requests from folders other than the Inbox. For example, if you move a meeting request with a rule to another folder, the “sniffer” process will find and process the meeting request from the new folder. Client-side logging General calendar issues are difficult to troubleshoot. Outlook 2007 SP2 introduces a new level of client- side calendar diagnostic logging that provides Microsoft Technical Support with much richer information to help customers isolate and fix calendar problems. Outlook 2003 has very basic calendar logging that provides much less diagnostic information and is more difficult to parse and translate into usable data. Informational updates Outlook 2007 introduced the idea of “informational updates” in the meeting request lifecycle. The default setting for manager/delegate configurations in Outlook 2007 is to send the meeting request to the delegate, and send only an informational copy to the manager. This lets the manager have information about the meeting, but the manager does not act on the request (accept/decline/delete). By having only the delegate respond to the meeting request, the reliability and predictability of the calendar is much higher. When using Outlook 2003, there is no choice for informational updates. You must choose to either send the meeting request to the delegate only, or to both the delegate and the manager. Either choice in Outlook 2003 can lead to problems. Either you have contentions when both parties respond to the meeting, or you have managers who do not see meeting requests and feel like they have missed meeting information. Conflict resolution The conflict resolution engine and diagnostic logging are significantly improved for Outlook 2007. Outlook 2003 delegates would not take advantage of the new improved code and potentially have to deal more often with old style “pick a winner” conflict resolution.

Customer-reported issues The following are some of the most commonly reported customer issues. Private item handling The notion of a “private” item in Outlook is not based on operating system or Exchange permissions. It is entirely a simple layer of filtering that is applied at the client level. For example, if you mark items as private in Outlook, they are only “private” to clients that enforce the filter. There is a delegate setting that controls whether delegates are allowed to see private item information. Customers report that in mixed mode scenarios, this setting is not retrieved properly in some cases. This does not mean that delegates are allowed to see private information when they should not. It means they are not able to see private item information when they should. Therefore, this issue does not lessen any privacy; it actually increases the privacy incorrectly. The most common cause of this problem is that a delegate, who never existed while the manager used Outlook 2003, is added by using Outlook 2007. As mentioned earlier, in this case, the delegate settings are written to the Outlook 2007 property only, and Outlook 2003 does not know how to retrieve the private item setting. Printing daily calendars The printing engine for calendars is redesigned in Outlook 2007. Customers have reported that printing daily calendars of a 2007 based manager from a 2003 delegate fails in some cases. This has not been reproduced internally. In fact, Outlook 2003 offers different calendar printing options for weekly and monthly views than Outlook 2007, and some customers prefer the layouts available in Outlook 2003. Attendee updates When you update the attendee list of a meeting, there are many complex possibilities. Some attendees may have been added, some may have been removed. The update might be for a recurring series, a standalone meeting, or an exception to a recurring meeting. Each of these updates requires complex and subtle handling of the meeting updates. Some customers report that in the mixed mode scenario, some of the attendee update scenarios are not consistent. This again is where it is important to have the latest builds of Outlook 2003 and Outlook 2007 since improvements and fixes in this area have been made incrementally over the years. Free/busy issues Meeting requests that are processed by Outlook 2003 delegates lose their recipient table. This means that free/busy information for the attendees is not available for the delegate. This is a long-standing design issue, and not specific to mixed version usage, but might be seen as a “symptom” of using Outlook 2003 on the delegate computers. For more information, see the following KB article:  309185 Meetings that are placed in an owner's calendar by a delegate do not display free/busy information for additional meeting attendees in Outlook (http://support.microsoft.com/default.aspx?scid=kb;EN-US;309185) Also for Outlook 2007 (with Microsoft Exchange Server 2007) there is an additional free/busy architecture (Availability Service, more granularity in the permissions options, caching of the shared folder), so free/busy issues and differences can be noticeable. This is especially true if any mailboxes are on Exchange Server 2007. General calendar risk areas The following are general calendar risk areas. Missing/duplicate meetings The Outlook calendar in today’s world is typically manipulated by a variety of software. When there is an inconsistency from any source, the result is seen in Outlook, usually in the form of a missing or duplicate calendar item. For information about how to best support and troubleshoot these issues, see the following KB articles:  899704 Description of common scenarios in which Calendar information may be removed from the Calendar or may be inaccurate (http://support.microsoft.com/default.aspx? scid=kb;EN-US;899704)  890436 How to troubleshoot missing and duplicate appointments in Outlook (http://support.microsoft.com/default.aspx?scid=kb;EN-US;890436) Troubleshooting challenges Cooperation with the Exchange Server team, significant data review, time to resolution for support cases, and need for access to executive’s computers for significant timeframes are all factors in resolving calendar issues. For information about how to help enterprise customers in their support engagements, see the following TechNet article:  Working with support to troubleshoot the Outlook calendar in an Exchange environment (http://technet.microsoft.com/en-us/library/cc891495.aspx) Sync software integration Mobile device synchronization is very popular among enterprise customers. Integration with synchronization software from RIM, GoodLink, Apple (iPhone and iPod), Windows Mobile, and Office add-ins have a large effect on calendar data. This can manifest itself as meeting lifecycle issues (“I accepted this meeting, but it says that I didn’t”), to processing issues (“this meeting never showed as tentative on my calendar”) to crashes, hangs, performance problems, etc. Being able to isolate problems to scenarios that involve the synchronization software or add-ins is often a crucial part of resolving the issues.

Summary Mixed version manager/delegate pairs were not a development or test target during the Outlook 2007 development cycle. Therefore, there is no practical way to provide a comprehensive list of potential issues or behaviors. This document attempts to present calendar differences, customer reported issues, and calendar issue handling recommendations to make the time delta where the versions are mixed more manageable.