Exchange 2010 Offers Compelling Reasons to Upgrade

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1 Exchange 2010 Offers Compelling Reasons to Upgrade By Shoshana Mahler and Paul Robichaux

2 Contents Journaling...2 Personal Archives...3 E-Discovery...4 Retention Policies and Tagging...7 Migrating to Exchange A Compelling Upgrade...9 Exchange 2010 Offers Compelling Reasons to Upgrade Exchange 2010, the latest release of Microsoft s very popular messaging and communication software, is being adopted by organizations of all sizes, both for use in their own data centers and also as a hosted solution. This adoption comes about because Exchange is a mature, robust product that has benefited from more than ten years of steady development, with continuous input from Microsoft customers driving its design and implementation. Microsoft cites three basic goals that guided the design of Exchange 2010: providing flexibility and reliability to reduce costs, increasing user productivity and satisfaction by giving them better tools to manage messaging, and providing improved compliance, retention, discovery, and governance tools. Flexibility, reliability, and productivity benefits in Exchange 2010 come from a combination of new features and refinements of existing ones. For example, the ignore thread feature in Exchange, which acts like a mute button for , is a new feature, while the new architecture of Database Availability Groups (DAGs) is arguably a refinement of the continuous replication features from Exchange Many of the compliance and retention features in Exchange 2010 are refinements of older features, but there are new ones as well. How well do these features work? Are they robust enough for enterprise use? What s their intended audience, and do they meet the needs of that audience? This paper will answer these questions by discussing key Exchange features in four areas: journaling, online archiving, e-discovery, and retention policy. We ll also discuss considerations for migrating to and implementing Exchange Journaling On its face, journaling seems like a very simple feature to implement. The goal of journaling is to make sure that a messaging system preserves an accurate copy of every message sent or received by any system user. As with so 2 Exchange 2010 Offers Compelling Reasons to Upgrade Sponsored by Sherpa Software

3 many other things, the devil is in the details. For example, a robust journaling implementation has to take into account the fact that a single message might have many recipients, some of which might be distribution groups. This means that the final addressee list of the message might contain the same person more than once. It must also take into account the fact that messages might be duplicated during transport, a process known in the Exchange world as bifurcation. Ideally, these duplicate messages should be recognized and omitted from the journal, without losing other messages that might superficially appear to be duplicates but are not. It s important to understand that journaling is a means of capturing messages, not storing them. In that light, the journaling features in Exchange are simple to understand because they only do one thing: capture messages. In Exchange 2010, the Hub Transport server is a central point of processing for all mail in the organization, whether it arrives from the outside or is internally generated. That is, every message must pass through a Hub Transport server by design. It may seem odd, but even if you have only one Exchange server, every message generated on that server passes through the Hub Transport. This is necessary because the Hub Transport server applies a variety of message policies, including Hub Transport roles and the journaling agent. The journaling agent is the Exchange component that is responsible for inspecting and capturing messages when they are submitted for delivery and when they are routed for further processing. This processing can take place according to rules you create that select which messages are journaled, which recipients are journaled, and where the collective messages should be sent. You might choose to collect only internal messages, only external messages, or all messages. The standard Exchange Client Access License [CAL] allows you to enable journaling at the mailbox database level; when you do so, all mailboxes resident in the database will be journaled. If you prefer, you may enable journaling for selected recipients, but that requires you to purchase the enterprise CAL for each user you want to include. There aren t many changes to the journaling features in Exchange 2010 compared to Exchange 2007, which isn t surprising because journaling is fundamentally a simple feature. One noticeable improvement is that it s somewhat easier to control the journaling of voic -related messages, including missed call notifications. Another, more significant new feature is that Exchange 2010 properly handles journaling of messages protected with Active Directory Rights Management Services. It s important to remember that journaling captures messages. What happens to them after they are captured, such as being archived, is more complex from both a technical and compliance perspective. Personal Archives Personal archives, a new feature in Exchange 2010, are specialized mailboxes linked to users primary mailboxes. Each primary mailbox can have one archive mailbox, and each can have a Figure 1: Creating a New Local Move Request Sponsored by Sherpa Software Exchange 2010 Offers Compelling Reasons to Upgrade 3

4 separate quota size. With SP1, the archive and primary mailboxes don t have to reside on the same database. Additionally, moving the archive database to a new location from the Exchange Management Console (EMC) is simple with the New Local Move Request wizard (Figure 1). With the flexibility in having the archive and primary mailboxes on separate databases, you can implement separate storage strategies for less frequently accessed mail. However, there have been reported performance hits from an end-user s perspective when the archive and primary mailboxes reside on separate servers. For the end-users, accessing the archive is like accessing another folder in Outlook (Figure 2). To make the transition even more seamless, endusers can search their archive in the same manner they would search another folder. End-users can even drag-and-drop messages into their personal archive. The only restriction end-users will have in accessing their personal archive is that it requires Outlook 2010 (in non-cache mode), Outlook Figure 2: Accessing Archives from Outlook Web App [OWA] or Outlook 2007 (requires the December 14, 2010 hotfix package). As mentioned, end-users can manually add data to the archives. You also can add data to the archives through retention policies. Administrators can use retention policies to automatically move data of a certain age from the primary mailbox into the archive mailbox. Currently in Exchange 2010, you can only base your retention policies on message age; there is no way to automatically move data into the archive based on any other criteria (e.g., message size, attachment size, and so on). Retention policies will be discussed in further detail later in this paper. Administrators can also add data to the archives by importing their PST files back into Exchange using PowerShell scripts. In fact, one of the goals of the personal archives is to replace the need for PST files. Both PST files and personal archives offer end-users a separate location to store their historical . However, PST files can be dispersed across your network, can contain duplicate messages, and are usually out of the control of administrators, making regulatory compliance and e-discovery challenging. By moving this data into the centralized personal archives, administrators can manage their archives using EMC or PowerShell in the same manner they would manage their mailboxes. Therefore, a major driver for organizations to replace PST files with personal archives is to promote better information management. E-Discovery Another new feature implemented in Exchange 2010 is e-discovery. E-Discovery is a complicated topic because it involves legal precedents, government regulation, corporate governance, and a number of other non-technical domains. Generally, the term discovery is understood to mean the process of searching for all the information that matches a subpoena or other legal demand. There are all sorts of well-defined laws that determine which types of business records are subject to e-discovery, the time frame in which they need to be produced, and so forth. Exchange 2010 does very little to help you understand which e-discovery requirements you may be subject to meeting. However, it does provide some tools to make things easier in the event that you receive an e-discovery request. 4 Exchange 2010 Offers Compelling Reasons to Upgrade Sponsored by Sherpa Software

5 Figure 3: The ECP Interface for Multi-Mailbox Searches in Exchange 2010 The core of e-discovery for electronic messaging systems is the ability to search a set of mail servers and find all the messages that match some type of criteria, such as who sent them, who received them, what s in them, and so on. The primary Exchange 2010 feature for meeting e-discovery demands is its ability to perform search operations across multiple mailboxes, a feature known as Multi-Mailbox Search. This feature itself might not seem like such a big deal; after all, searching a mailbox or mailboxes for content is a ubiquitous feature of most mail clients and many mail servers. However, one key difference in Exchange 2010 is the interface for performing the searches: the new Exchange Control Panel (ECP). ECP provides a search interface that can be given to non-technical users, such as corporate legal teams or even outside counsel. Figure 3 shows some interesting things about the new ECP interface for performing Multi-Mailbox Searches. As you can see, there is one search pending, named Project Orion. The time, date, and user associated with the search are shown, along with indication that Exchange is estimating how long Sponsored by Sherpa Software the search will take a useful thing to know when you re searching many mailboxes. Exchange 2010 supports the following basic search criteria: Sender or recipient addresses Date ranges A set of mailboxes Data types (including IM conversations recorded to the Conversation History folder, calendar items, notes, and Journal entries) Attachment types Attachment content You may combine these criteria using the standard Boolean AND and OR operators. Figure 4 demonstrates a New Mailbox search in Exchange When you create a new search, you specify the target mailbox where results should be stored. This target mailbox is a special mailbox called a discovery mailbox. A folder with the same name as the search will be created in the discovery mailbox. You also have the option to enable the deduplication of search results. In such searches, Exchange will remove redundant messages from Exchange 2010 Offers Compelling Reasons to Upgrade 5

6 name Discovery Search Mailbox. More discovery mailboxes can be created by using the PowerShell (not the EMC), and will be created with no access permissions. Therefore, you will need to assign who has access to the discovery mailboxes, as well as who may perform searches. An important aspect of Exchange 2010 s e-discovery capabilities is its associated access controls. Prior versions of Exchange had a limited number of administrative roles that could be assigned to users, such that each user who needs to perform e-discovery searches has to have administrative rights. In Exchange 2010, Role-Based Access Controls (RBACs) are used to delegate access to specific functions. Every user who needs to perform e-discovery searches must be a member of the RBAC group called Discovery Management. All other users (and even administrators) cannot perform e-discovery searches. For example, your legal team can be members of the Discovery Management group so they can perform e-discovery searches without having any other type of administrative access to Exchange It is considered a best practice to leave the Discovery Management group empty, and to only assign members when they need to perform a search. This helps reduce the risk of unauthorized searching or searches which exceed the authority given to the role holders. However, RBAC s flexibility somewhat increases the complexity of Exchange Figure 4: A New Mailbox Search your search results. Depending on the reasons you're performing an e-discovery search, deduplication can be a significant time savings, but it may not be legally permissible. When creating a new search, it s important to consider the question of where the search results go. Because Exchange 2010 copies messages to a discovery mailbox, you re guaranteed that the discovery mailbox will have a complete set of search results, which can then be acted upon without touching the original source. However, if all you want to do is a quick scan for items of interest, you may contend with having these items stored in a shared discovery mailbox. By default, there is one discovery mailbox with the display In addition to the basic mechanism of being able to search multiple mailboxes for a given set of words, phrases, or attachments, Exchange 2010 lets you save the searches and repeat them as necessary. This is a useful way to quickly define a set of standardized search terms and check to see who has been, or is, using them. In Exchange 2010 SP1, you can add annotations to individual search results. For instance, Microsoft uses the example of adding a case number to messages that you find, but you can add any other kind of metadata that makes sense. In addition, a script on the Exchange team blog allows you to schedule searches that run periodically. This can be very useful if you regularly perform the same searches, or if you need to see how search results change over time. It is not, however, a complete substitute for an e-discovery 6 Exchange 2010 Offers Compelling Reasons to Upgrade Sponsored by Sherpa Software

7 system that can perform live searches updated on demand. Exchange 2010 s Multi-Mailbox Search has a couple of limitations. First, it can only search Exchange 2010 servers. Mailboxes that exist on legacy Exchange servers, as well as non-exchange servers, cannot be searched. Additionally, PST files cannot be searched. Second, the Multi-Mailbox Search requires the enterprise CAL for each user s mailbox you wish to search. Therefore, it s a good idea to determine how many mailboxes you actually need to search to ensure that you have the correct number of CALs. (You can always search individual mailboxes using the search-mailbox command, which gives you a simple way to quickly search a single mailbox when needed.) Retention Policies and Tagging Exchange 2010 introduces automated retention policies and retention tags, which make up the core of Microsoft s Messaging Records Management (MRM) feature. The MRM allows you to create Exchange policies to comply with company policy, government regulation or legal needs, and thereby reducing your legal risks. The MRM was introduced in Exchange 2007, but it required frequent or active user interaction in practice. Accordingly, the new MRM features in Exchange 2010 are more highly automated. To implement a retention policy, you will first need to define your retention tags. There are three types of retention tags: Personal Tags, Retention Policy Tags [RPTs], and Default Policy Tags [DPTs]. Personal tags are applied to folders or individual items by the end-user in Outlook 2010 or OWA. A built-in set of personal tags is available, including delete after 180 days and business-critical. However, Personal Tags require enterprise CAL. RPT applies to the default folders such as the Inbox or Sent Items (but not the Contacts folder). DPT, which might be the most confusing, applies to any item that does not have another tag applied to it (either an RPT or a Personal Tags). Each retention tag has its own retention age and action. The retention age specifies how long a message is kept after it arrives in a mailbox, and the retention action determines if the item is moved to the personal archive, moved to the Recoverable Items folder (dumpster folder) or permanently deleted. The set of available actions varies according to the type of tag. Under some circumstances, items that are deleted may be retained by the Exchange 2010 litigation hold feature (a topic outside the scope of this paper), whose job it is to keep an accurate record of items in a mailbox even when users attempt to delete them. One of the major limitations with this feature is that there is no other criterion other than age for retention tags. Therefore, you cannot apply retention tags based on size, keywords, and so forth. Retention tags can be overridden with disable tags, such as the disabled personal tag Never Delete. Once you have defined your tags, the next step is to define your retention policies. Retention policies are essentially sets of tags that you apply to individual mailboxes. That is, you add one or more retention tags to a retention policy, and then apply the retention policy to a mailbox. Each policy may contain one DPT, one RPT for each of the default mailbox folders (calendar, inbox, and so on), and any number of Personal Tags. A mailbox can be linked to several retention policies or none. Each of these policies will apply a mix of tags to ensure that you retain the correct items for the right length of time and in the appropriate locations. The policies themselves are applied to the mailboxes by an Exchange service known as the Managed Folder Assistant. When it applies the policy, the Managed Folder Assistant scans through each item and determines if it meets the retention tag s retention age. If the item does not qualify for retention (i.e., past its retention age), the Managed Folder Assistant applies the retention tag s retention action. Prior to Exchange 2010 SP1, the Managed Folder Assistant ran on a schedule. In SP1, this service is now a throttle-based assistant; that is, the Managed Folder Assistant can always be running or running for a specified period or interval. The implementation of this feature is complex. For example, it's important to remember that Personal Tags trump the other retention tags. If you have a Personal Tags available to users that counteracts a DPT or RPT and users are free to apply it, it may have a negative effect on your retention policy. For instance, users could apply the Never Move or Never Delete Personal Tags to keep items in their mailbox even if there was an RPT or a DPT that would have moved the item. This may or may not be what you actually want, Sponsored by Sherpa Software Exchange 2010 Offers Compelling Reasons to Upgrade 7

8 which is why implementing retention policies requires a great deal of thought, planning, and testing. The best way to take advantage of this feature is to carefully test your proposed policies to verify that they work the way you expect and that they meet your actual retention needs prior to actually deploying the policies. Microsoft has attempted to simplify things by providing a default policy for archiving and retention in SP1, named the Default Archive and Retention Policy. This policy includes: Several personal tags with various retention ages, ranging from one week to never, for deletion The DPT that moves items to the user s personal archive after two years An RPT that moves items from the Recoverable Items Folder to the personal archives after 14 days The Default Archive and Retention Policy is automatically applied to a mailbox if it does not already have a retention policy when its personal archive is enabled. However, you will need to configure and start the Managed Folder assistant, which can only be done through PowerShell in Exchange 2010 SP1. Migrating to Exchange 2010 If you have decided to migrate to Exchange 2010, one of the first things you will need to consider is its requirements. If you re currently using Exchange 2000 or earlier versions, you will have to upgrade to Exchange 2003 or 2007 prior to migrating to In fact, Exchange 2000 and 2010 cannot exist in the same domain. Even if you re transitioning from Exchange 2007 to 2010, which is supposed to allow end-users continued access to their mailboxes during the move process, there is still a potential for workflow disruptions. You should keep this in mind while planning the migration. Additionally, you will have to consider upgrading Outlook. Exchange 2010 only supports Outlook 2003, 2007, and 2010 versions (and OWA). However, if you would like your end-users to have access to their personal archives through Outlook, they will require Outlook 2010 or Outlook 2007 with the December 14, 2010 hotfix package installed; you will need to take this into consideration when planning your rollout. Also, if you plan on allowing continued use of Outlook 2003, you will need to enable Public Folders because information such as the free/busy data needed for Outlook 2003 calendars is stored in the Public Folders. Other compatibility issues you will need to address are your third-party add-ons, such as your anti-virus and mail management software. It s possible that you may need to purchase new versions in order to support Exchange To complicate matters even more, many third-party add-ons do not currently support Exchange 2010, or they do not natively support a mixed Exchange environment. Once your organization decides to migrate to Exchange 2010, proper planning and testing are essential to ensure a smooth and timely transition, and will ensure all of the Exchange 2010 requirements can actually be met prior to deployment. Because you re introducing new hardware and software into your environment, testing is essential to a successful migration. Testing will help you identify and potentially mitigate any risks that you may encounter during the migration process, and will help you prevent any workflow disruptions. For instance, there have been reported issues with updating AD through the EMC. If you run into such issues, using PowerShell to update AD will likely resolve them. However, if you failed to discover this prior to migrating all of your end-users, they could lose access to their mailboxes until AD is properly updated. With testing, you will identify this problem and will know if PowerShell is needed to update AD. Additionally, proper planning and testing will help to ensure all the necessary resources required for the migration are obtained. Therefore, if you re considering migrating to Exchange 2010, good project management is crucial. Once your organization has decided to migrate to Exchange 2010, it s likely that you will have to take on another migration challenge: moving the items from your PST files back into the Exchange server. With Exchange 2010, you have the option to move data from PST files into the end-users archive mailbox as well as their primary mailbox. 8 Exchange 2010 Offers Compelling Reasons to Upgrade Sponsored by Sherpa Software

9 As mentioned before, there are many reasons organizations are interested in importing their PST files into the Exchange server. For instance, managing data that is dispersed across the network is much more difficult than managing data that exists in a centralized location. If your organization decides to migrate your PST files into your Exchange server, you can have end-users open the PST files in Outlook and copy the items into their Exchange mailbox or archive (Outlook 2010 only) use PowerShell scripts to move items into a mailbox or archive use third-party solutions The seemingly least complicated option would be to have your end-users manually copy the items from their PST files into your Exchange server using Outlook. However, this is a very laborintensive task that may be too much for a typical end-user to perform. Additionally, administrators have little to no way of ensuring that all of the data has been moved. The risks that are introduced with this method make it an unreasonable and unlikely option. Another way you can import your PST files into Exchange is by using PowerShell scripts. If you are not familiar with using the command shell, it is not the most user-friendly interface. For example, the PowerShell command below takes the items from the PST files in a specified network share and imports the data into the appropriate mailbox: Dir \\SERVER01\PSTshareRO\Recovered\*.pst %{ New-MailboxImportRequest Name RecoveredPST -BatchName Recovered -Mailbox $_.BaseName -FilePath $_.FullName -TargetRootFolder SubFolderInPrimary} In addition to its lack of intuitiveness, several other limitations exist. First, you will still need to locate the PST files. Second, there is no way to circumvent encrypted or password protected PST files. And finally, there is no way to process a PST file that is open in Outlook. To circumvent this and other issues, Group Policy can be used. Group Policies can be used to locate the PST files located on your end-users desktops, copy the PST files to a network share, and then prevent new PST files from being created. Although applying a Group Policy relies on the end-users to log off and on, this will also ensure that the PST files are no longer open in Outlook. By combining Group Policies and the import feature in Exchange 2010, you can successfully import your PST files into Exchange. However, the limitations that exist with this method still make it an impractical method for many organizations. For such organizations, using a third-party solution would likely meet their migration needs. There are many third-party solutions available that, through a Graphical User Interface (GUI), can import your PST files into your Exchange server. Each third-party solution is different, so it s important that you research and test these solutions prior to implementing them. For example, Sherpa Software s Mail Attender for Exchange can import your PST files back into Exchange, including into the primary mailbox, archive mailbox, and Public Folders. Additionally, Mail Attender can automatically find and process PST files across the network (server-based PST files) as well as on end-users desktops (desktop-based PST files) process desktop-based PST files that are currently open (and locked) in Outlook process encrypted or password protected PST files Mail Attender will even attempt to recover corrupted PST files, and can provide reporting features for quality assurance and project planning. Because of the added capabilities, many organizations require third-party solutions to migrate their PST files back into Exchange. A Compelling Upgrade With all the added features, Exchange 2010 is proving to be a compelling Upgrade for many organizations. Microsoft has clearly delivered many of the benefits they were aiming for in their tripod strategy of reducing cost, increasing user productivity, and enabling more robust security, compliance, and discovery. However, it s clear that not every aspect of these new features is completely developed, or even has inherent limitations. As a result, there are still a number of functional areas where Exchange 2010 might still benefit from third-party products that enhance its features, or provide capabilities that Microsoft simply does not implement: PST management Although Exchange 2010 includes tools for importing and exporting data Sponsored by Sherpa Software Exchange 2010 Offers Compelling Reasons to Upgrade 9

10 in PST files from the server, without requiring a separate client, it does not include tools for discovering PST files, auditing their use or contents, or otherwise managing. Before you can import them, you have to find and analyze them. One third-party software that provides this capability is Sherpa Software s Mail Attender for Exchange. With its desktop agent, all PST files that exist in your network can be discovered, analyzed, and migrated back into your Exchange server. Archiving The concept of an integrated personal archive is a solid one, because it enables users to retain access to their mail without requiring them to deal with PST files. However, that access is limited at present to OWA, Outlook 2010 and Outlook 2007 (with the December 14, 2010 hotfix package), with no current facility for Macintosh or mobile users to gain access to their archived material. Additionally, the criteria in which you implement archiving is restricted solely to message age. Third-party solutions, such as Sherpa Software s Archive Attender for Exchange, overcome many of these limitations. You can archive messages based on size, keywords, and so forth as well as archive only attachments while leaving the message intact in Exchange. Additionally Archive Attender can provide archiving solutions that are not limited to Exchange 2010 mailboxes as well as provide end-user access to their archives through all versions of Outlook and OWA. E-Discovery One of the major limitations with the Multi-Mailbox Search is that it requires purchasing enterprise CAL s for every mailbox you wish to perform such searches on. This means that the price to implement Exchange 2010 and perform these searches will be more expensive. The built-in Multi-Mailbox Search functionality is a major improvement over the tools available in previous versions of Exchange, but it lacks features commonly found in standalone e-discovery systems, including Sherpa Software s Discovery Attender for Exchange. For organizations with light to medium discovery requirements, the built-in capability is probably enough. But for organizations that must frequently perform discovery searches and require something more than simple Boolean searches or that would like to search for items outside of Exchange 2010 mailboxes, a third-party solution may be appropriate. Retention The retention system in Exchange 2010 is very flexible, but also quite complex. It will take a good bit of study, and a great deal more deployment experience, before the best practices for deploying and using this feature are well understood. Even with its increased flexibility, retention policies can only be applied to Exchange 2010 mailboxes. If you would like to apply such polices to other Exchange mailboxes or PST files, you will need a third-party solution such as Sherpa Software s Mail Attender for Exchange. As previously mentioned, Mail Attender allows you to manage any Exchange store that may exist in your environment. Therefore, any organizational policies or government regulations that you must comply with can be done so with Mail Attender for all of your Exchange mailboxes and PST files. Shoshana (Shani) Mahler is the Technical Support Specialist for the Microsoft Exchange products at Sherpa Software. Primarily responsible for pre-sales technical support, she is also a major contributor to Sherpa Software s technical documents and is one of the lead consultants for Sherpa Software s professional services. Paul Robichaux is a senior contributing editor for Windows IT Pro and a Microsoft Exchange MVP and MCSE who specializes in helping people understand how to get the most from Exchange. Paul's most recent book is the Exchange Server Cookbook (O'Reilly and Associates) and he blogs at 10 Exchange 2010 Offers Compelling Reasons to Upgrade Sponsored by Sherpa Software

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