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Auditing Privileged Operations and Mailbox Access in Office 365 Exchange Online

Tue, 27 Dec 2016 10:16:02 GMT

Email remains one of the most heavily used communications mediums within organizations today. With as much as 75 percent of your organization’s intellectual property stored in email[1], Microsoft Exchange is for all practical purposes a treasure trove of organization’s most valuable secrets—just waiting for inappropriate access.

Regulatory bodies realize this and therefore email and compliance go hand in hand-in-hand. So IT needs to keep a watchful eye on exactly who is accessing what within Exchange Online. And that focus shouldn’t be only on the people you trust, such as those who have been granted access to a given mailbox, but on any user. IT needs to help ensure visibility into the actions of potential threat actors who might have hijacked privileged accounts. The first thing external threat actors do after infiltrating your network is attempt to identify accounts that have elevated permissions. And those accounts can have access to the sensitive information stored within Exchange Online.

For years, Microsoft has enabled an audit trail within on-premises Exchange Server. The same capability exists for Exchange Online—with some improvements to boot—giving IT organizations visibility into actions performed by administrators and regular users alike. But be forewarned: You’re largely on your own here. Microsoft has provided some functionality via administrative consoles, but the ability to successfully enable, configure, and audit Exchange Online events depends fairly heavily on PowerShell[LP1].

The challenge isn’t configuring the auditing of events; that part is simple. Rather, the challenge is finding the event or events that are pertinent to the auditing query in question. If you’ve spent any time in Event Viewer, you know how it feels to rummage through countless thousands of event entries, trying to find the one entry you’re looking for.

Microsoft has taken great strides to provide you the tools necessary to simplify the process of auditing. Still, a bit of work remains to enable, configure, and retrieve meaningful audit data.

This whitepaper explains those necessary steps and provides guidance for properly auditing changes to your Exchange Online environment within Office 365. The paper also covers ways to focus your auditing lens on the right what, who, and where so that you can quickly and accurately find answers to those sometimes difficult auditing questions. 

Auditing Experts – Quest


Understanding what’s going on within Exchange Online involves much more than the ability to centralize audit data. To truly audit such complex environments, you need a deeper understanding of each event and its detail, how audit events correlate, and what that information means to the organization—along with the ability to make the data understood.


Quest Change Auditor is the culmination of tens of thousands of hours of work dissecting every auditable event over a variety of platforms and applications. This effort turns raw, indecipherable information into intelligent detail, from which an IT organization can obtain actionable insight.


Look for auditing insights from Quest throughout this paper.

Connecting to Office 365 to Enable and Configure Auditing

The first step is to enable auditing. Auditing is disabled by default, as not every organization is required to — or even interested in — auditing what happens within Exchange Online. As previously mentioned, much of this step happens in PowerShell. You’ll need to connect to Exchange Online via PowerShell so that all commands are run against your instance of Exchange Online.

Open a PowerShell window. You don’t need to be a local admin to run Exchange commands against the cloud, but you do need appropriate permissions within Exchange Online; more on these permissions soon. To connect to Exchange Online, you’ll run four commands.

Set-ExecutionPolicy RemoteSigned

This command tells PowerShell that any scripts that are downloaded by a trusted publisher (Microsoft, in this case) can run on the local computer.

$UserCredential = Get-Credential

This command displays a login dialog box that you use to store an Office 365 admin credential (which does not necessarily need to be the same credential you used to start the PowerShell window) as a parameter for use in the third command.

$Session = New-PSSession –ConfigurationName Microsoft.Exchange –ConnectionUri -Credential $UserCredential –Authentication Basic –AllowRedirection

This command establishes a new PowerShell session with Office 365, using the provided credentials and the specified URL. The command stores all this information in the $Session variable.

Import-PSSession $Session

This command imports commands (e.g., cmdlets, functions, aliases) from the remote computer (i.e., Office 365) into the current session. At this point, you’re properly connected to Exchange Online and can begin auditing your Exchange Online environment. 

Quest Insight – What Should You Be Auditing?

Exchange Online can be configured to generate a ton of information—which, of course, means more data for you to sift through. Because you are essentially in control of how much audit data is generated, you can determine which activities to include. You can focus on three categories of audit activity:


·         Message tracking is the actual flow of messages from one user to another. At a minimum, this category can be used to show who is emailing whom, such as whether email is being sent to a competitor. On a larger scale, message tracking can be used with analytics to see how the business uses email. This tracking is useful to see how internal messaging flows; for example, from one department to another. Message tracking can also be used to see the flow of traffic in and out of the organization; for example, which domains send or receive the most email. You can use the Get-MessageTrace cmdlet to retrieve a list of messages that meet query criteria such as sender or recipient address, date range, or source IP address. This activity is most appropriate when a review of specific sent and received messages is needed in addition to a review of mailbox contents. This tracking can also be useful when connected to a SIEM solution, using keyword alerts to identify inappropriate messages.

·         Admin operations involve any actions that are taken within Office 365, including actions by your IT team or Microsoft (which maintains the Exchange Online instance). Admin operations, such as assigning permissions to a mailbox or setting up forwarding rules, can play a key role during an audit; even IT can play a role in inappropriate behaviors.

·         Non-owner mailbox access occurs whenever someone other than the owner accesses a mailbox. This category is important when sensitive information has been inappropriately accessed or forwarded, and the focus is on identifying who is responsible.


Because message tracking typically falls outside an IT security audit, this paper foregoes that topic and focuses on the other two audit areas, which directly affect your organization’s ability to document access, changes, and actions that would be of interest during an audit.

Auditing Admin Operations

Auditors are big believers in the ability to watch the watchers. Questions around changes that IT has made are just as important as those that focus on users exercising access that IT has granted. For example, if an audit revolves around the CEO forwarding intellectual property to a competitor, a good auditor doesn’t just accept that the CEO forwarded the information. Rather, the auditor also asks who has been granted permissions to the CEO’s mailbox—and who in IT granted those permissions.

Both security and compliance initiatives are useless without auditing admin operations. Because there are no preventative controls for admins (who need the ability to do “everything” to get their job done), the need for controls that detect and deter inappropriate behavior is necessary. By putting an audit trail in place, you create accountability. After all, knowing that they’re being audited tends to encourage admins to keep their behavior in check.

When it comes to Exchange Online, a number of actions can indicate malicious activity. For example, the exporting of a mailbox doesn’t require logging on to the mailbox; IT can simply export and review the local PST. Therefore, IT logging on to an exported mailbox should trigger non-owner mailbox auditing. Another example is granting permissions: IT could assign a cohort inappropriate permissions to another user’s mailbox, and then remove those permissions after improper access is completed. Unless you have non-owner mailbox auditing enabled, this access would go completely unnoticed.

You can see why admin operations need to be included as part of your auditing strategy. Everything an admin does within Exchange Online is ultimately a PowerShell command, so Exchange audits admin activity at the PowerShell level. Each time an audited cmdlet is run, the action is logged.

To check which auditing is enabled within your organization, you can use the Get-AdminAuditConfig command, shown in the following figure.

Place specific focus on the AdminAuditLogCmdlets, AdminAuditLogExcludedCmdlets, and AdminAuditLogParameters fields, which identify whether every admin operation is audited or a subset.

Quest Insight – Age Limits

By default, admin audit data is kept for 90 days (as indicated by the AdminAuditLogAgeLimit value in the previous figure). You might want to consider extending the retention time. Organizations that perform annual audits should consider extending this value to more than 365 days (one year).

To enable auditing, you need to leverage the Set-AdminAuditLogConfig cmdlet:

Set-AdminAuditLogConfig –AdminAuditLogEnabled $true

Quest Insight – Enabling Just the Right Amount of Admin Auditing

Each organization has different auditing requirements, so auditing of admin actions isn’t always as simple as “just audit everything.” If you simply enable all admin auditing, you’ll see all the changes that Microsoft makes on the back end, which might be something you don’t care to filter through during an audit.


Because admin auditing is based on the premise that every performed action relates to running a PowerShell cmdlet, the Set-AdminAuditLogConfig cmdlet enables you to specify which cmdlets and cmdlet parameters to include or exclude. Be sure to note that auditing of commands in Exchange Online does not include read-only types of commands, such as any Get and Search commands.


You can specify individual cmdlets or use wildcard characters to denote a group of cmdlets:


Set-AdminAuditLogConfig –AdminAuditLogEnabled $true

-AdminAuditLogCmdlets * -AdminAuditLogParameters *

-AdminAuditLogExcludedCmdlets *Mailbox*, *TransportRule*


 So, how do you get this information out of Office 365?


There are two ways to extract admin auditing information from Office 365: via PowerShell or by using the Office 365 Security & Compliance portal.

Auditing via PowerShell

Using PowerShell to audit can be accomplished by using the Search-AdminAuditLog cmdlet. When you use this cmdlet with no filtering parameters, you obtain the last 1000 entries. This information shows the cmdlets and parameters that were used, who ran each action, whether the action was successful, the object affected, and more, as shown in the following figure.

The Search-AdminAuditLog cmdlet results don’t provide comprehensive detail; for example, the Caller field, which specifies which users called the cmdlet, is blank. So the cmdlet is more useful if you’re trying to get an overview of changes made rather than performing an actual audit.

You can alternatively use the New-AdminAuditLogSearch cmdlet to receive an emailed XML report of the log entries within a specified date. For example, in the following figure, you can see that an admin is adding full mailbox permissions to the user bbrooks.


Quest Insight – Filtering Cmdlet Searches

The basic cmdlets return a large amount of data that might include the behind-the-scenes management actions performed by Microsoft. So it’s important to use the cmdlet’s parameters to filter the noise of all the resulting data.


Both the Search-AdminAuditLog and New-AdminAuditLogSearch cmdlets enable you to filter by date, cmdlet used, parameters used, the user who performed the action, whether that user is external to the organization, and the objects that the action affected.


By using some of these filters, you can hone down the results to a more pertinent set of data, increasing your productivity by more quickly finding the answers you need. 

Auditing via the Office 365 Security & Compliance Portal

Those who simply aren’t “PowerShell people” and would rather use a management console can take advantage of the Audit Log Search functionality in the Office 365 Security & Compliance Portal. In the pre-created Activities, you can begin your audit by simply selecting a management action, such as the delegation of mailbox permissions in the following figure. You can use the additional filter fields to further refine the results to the few that meet your criteria.

Be aware that the Activities are a double-edged sword. You are limited to those activities (with the supported filters) and cannot generate custom search scenarios of your own. For example, you can’t search for every time someone exported a mailbox (at the time of this writing).

Results can be exported as well, for reporting and further analysis.

You will experience a few limitations should you choose to use the console. First, you’re limited to only 90 days of audit data — and there’s no way around that. In addition, although audit data is available to PowerShell cmdlets within 30 minutes, accessing the same data via the console can take up to 24 hours.

Auditing Non-Owner-Mailboxes

Auditing administrative actions helps to identify the events leading up to inappropriate activity within Exchange. But the real value is found in auditing access to the data that is stored within Exchange. The assumption with non-owner mailbox auditing is that the mailbox owner is using the mailbox appropriately. (Sure, cases of insider misuse by a mailbox owner exist, but those issues are addressed by message tracking.) So, the focus shifts to any non-owners that access a given mailbox.

In general, you should be concerned any time a non-owner views, sends email on behalf of, or deletes email in another user’s mailbox. Delegates — a part of Exchange for as long as the product has been available — are a vital part of the productivity of many users who require assistance from other employees. But because delegate access exists, and because inappropriate delegate access can be granted, auditing non-owner access to mailboxes provides an important piece of data. 

Quest Insight – Which Mailboxes Should You Audit?

Which mailboxes to audit is a valid question. Find the answer by considering these questions:


·         Is there any delegate access? If so, turn on auditing. This way, you have an audit trail of every time the delegate accesses the owner’s mailbox and what was done.

·         Does the mailbox contain sensitive data? Mailboxes that are owned by users who regularly send and receive financials, intellectual property, legal documents, and so on might be prime targets for insider activity. Even when no delegates are assigned to a mailbox that contains sensitive data, enable auditing proactively so that you have an audit trail of any and all access to the mailbox.


Unlike admin auditing, which is an organizational-wide audit setting, non-owner mailbox auditing is enabled on a per-mailbox basis. Audit log entries are retained, by default, for 90 days—a value that can be customized.

You can enable non-owner mailbox auditing at three levels, each with specific audited actions:

  • Admin. This level audits actions by admins who have not been granted delegate permissions to a mailbox.
  • Delegate. Anyone who is assigned permissions or given Send on Behalf of permissions is considered a delegate.
  • Owner. Auditing for the mailbox owner is typically disabled, as it isn’t relevant to audits. In addition, enabling owner auditing generates a great deal of information. Non-owner access is generally infrequent and limited in scope (e.g., an assistant sending out calendar invites for their boss, someone in IT finding a specific message), whereas audits of owner access encompass every email created, read, filed, deleted, and so on.






















































Enabling Non-Owner Mailbox Auditing

Like admin auditing, non-owner mailbox auditing is enabled by using PowerShell via the Set-Mailbox cmdlet. As previously mentioned, this action is accomplished on a per-mailbox basis and requires that you specify which level or levels of auditing (admin, delegate, or owner) you want to enable:


Set-Mailbox –Identity “John Smith” –AuditDelegate SendOnBehalf,FolderBind –AuditEnabled $true


AuditDelegate in this command. This parameter enables mailbox auditing, but only for delegate access and only for the specified actions. You either need to perform this command a second time to configure auditing of Administrator access, specifying which actions should be audited (as shown in the following command), or include the AuditAdmin parameters in the same execution of this cmdlet:


Set-Mailbox –Identity “John Smith” –AuditAdmin Copy,MessageBind

-AuditEnabled $true


Organizations that audit the mailbox access of every user must enable mailbox auditing for new users. This approach might require a bit more PowerShell scripting, to continuously perform a search for a user account with a recent create date and to run the previous commands against that account.

Quest Insight – Which Actions Should You Audit?

You should enable both admin and delegate access to help ensure that any (and every) instance of non-owner access is recorded. Auditing of most of the previously mentioned admin actions is automatic whenever auditing is enabled for a given mailbox, with the exception of MessageBind (which for all intents and purposes can be considered a reading of a message) and Copy. Auditing of these actions needs to be enabled separately (as explained earlier). Also note that whenever an admin is assigned Full Access to a mailbox, that admin is considered a delegate user and is audited as such.


Like admin, some delegate actions (i.e., Create, HardDelete, SendAs, SoftDelete, and Update) are also automatically audited. Therefore, you need to enable auditing for any other actions that you want to log.


Some organizations use solutions that scan mailboxes for compliance, identification of sensitive data, categorization for legal purposes, and so on. Such solutions might trigger bogus events because of their access of a given mailbox. In such situation, you can use the Set-MailboxAuditBypassAssociation cmdlet to bypass auditing for a specific, trusted account.

Now that you have enabled mailbox auditing, how do you get your audit logs out?

This process is a bit complicated, as it depends on how many mailboxes you need to audit, how much detail you want to obtain, and whether you need the raw audit data or a report format. You have a few options:

  • Synchronously via PowerShell. You can use the Search-MailboxAuditLog cmdlet to search a single mailbox’s audit log entries. The cmdlet displays search results in the Exchange Management Shell window and provides limited detail that might not meet your auditing requirements.
  • Asynchronously via PowerShell. You can use the New-MailboxAuditLogSearch cmdlet to search through the audit logs of one or more mailboxes, with the results sent to a specified email address as an XML file. If you want to pull audit data into your SIEM solution, use this option. Should your cmdlet query criteria generate too many results, then the received email simply informs you that the query was a failure. You’ll need to further hone the results to a smaller data set, potentially requiring the combination of multiple XML files to represent a complete audit of all actions. Be aware that Exchange 2016 allows only 10 searches of this type per mailbox within a 24-hour period.Exchange admin center reports. From within the Exchange admin center’s reports section (not the Office 365 Security & Compliance portal), you can run a Search for mailboxes accessed by non-owners report. However, you cannot export this data.
  • Office 365 Management Activity API. Microsoft provides a RESTful API to access audit data. This API requires some significant development, so it might not be an option for most organizations. However this is the only viable option for getting your all your audit data out of the cloud and into a compliance-ready secure archival and monitoring platform. To be compliant you have to use this API.

It can take up to 24 hours for events to show up in the unified audit log where they are stored, so you should expect some latency around audit requests. Also note that none of these options make it truly easy to obtain the information you need. Some don’t provide the necessary granularity, whereas others require that granularity if they are to be valuable. Think of each option more as another tool to access raw data than as an auditing solution designed to provide you with correlated, formatted intelligence around performed actions.

Meeting Compliance and Security Requirements

The good news is that Office 365 does capture the audit data you need. But compliance and security require more than just capture audit data. You have to protect, archive and most importantly monitor that audit data. And monitoring means correlating with other security information from your environment so that you can actually detect attacks and misuse.

So the bad news is that if there is no way you can meet enterprise compliance and security requirements with the out of box functionality of Office 365. You must either write your own application to access the Management Activity API or exploit a solution that does that for you.

Enter Quest Change Auditor. Change Auditor now integrates audit logs from Exchange Online with the rest of the activity Change Auditor collects, normalizes and monitors from all over your network. The latest version of Change Auditor implements the Management Activity API and other APIs from Office 365 to automatically collect Exchange Online mailbox and administrator audit logs. Change Auditor brings to Exchange Online the same Who, What, When and Where capability ChangeAuditor is famous for. And the cool thing is now you see what a given user like Bob is doing both in the cloud and on your internal network because ChangeAuditor already monitors

  • Active Directory
  • SharePoint
  • Windows
  • SQL Server
  • Network Attached Storage
  • Lync
  • VMware

You can’t be compliance without monitoring your environment and that fact doesn’t go away when you move to the cloud. Office 365 captures the activity required by enterprises for compliance but it’s up to you after that. Change Auditor solves this issue and puts cloud activity and on-prem events on the same pane of glass.


About Randy Franklin Smith

Randy Franklin Smith is an internationally recognized expert on the security and control of Windows and AD security. Randy publishes and wrote The Windows Server 2008 Security Log Revealed—the only book devoted to the Windows security log. Randy is the creator of LOGbinder software, which makes cryptic application logs understandable and available to log-management and SIEM solutions. As a Certified Information Systems Auditor, Randy performs security reviews for clients ranging from small, privately held firms to Fortune 500 companies, national, and international organizations. Randy is also a Microsoft Security Most Valuable Professional.


Monterey Technology Group, Inc. and Dell Software make no claim that use of this white paper will assure a successful outcome. Readers use all information within this document at their own risk.

[L1] Osterman Research, 2015

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