Why PowerShell Scripts Might Need Updates After Microsoft Changes the Name Property for New Mailboxes

The Exchange Online name change for mailboxes will roll out at the end of May, 2022. The change only applies to new mailboxes, but its introduction creates some interesting challenges for PowerShell scripts that process mail-enabled objects, including some good side-effects. In this post, we discuss some of the issues we’ve already encountered.

Project Monarch “One Outlook” Build Leaks

A leaked build of Project Monarch’s “One Outlook” client created some excitement last week, but when you examine the details of the client and what it can do, it’s really just a prettier version of OWA for Exchange Online. That doesn’t mean that Microsoft hasn’t done a bunch of software engineering to prepare the ground to accelerate progress toward the final client. Microsoft has also provided a way to block people using the client, with promise of an official beta soon.

Countdown Accelerating to the Big Basic Auth Turnoff

October 1, 2022, is when Microsoft begins the final process of removing support for basic authentication for 7 email connection protocols from Exchange Online. The process will take several months to complete, and when it’s done, Office 365 will be a safer place that attackers will find more difficult to penetrate. But it’s time for tenants to prepare, if you haven’t already done so, and we highlight some critical points from Microsoft’s most recent post on this topic.

Outlook’s Dislike for Moderated Distribution Lists

I’m not sure people use moderated distribution lists with Exchange Online all that much, but those who do might be frustrated by a client inconsistency between OWA and Outlook. OWA can expand the membership of a moderated distribution list; Outlook for Windows cannot. It’s a small point. Maybe Project Monarch will help…

Exchange Online Plans Changes to Make Mailbox Identification More Effective

Exchange Online plans to change the format of the Name and Distinguished Name mailbox properties. The idea is to make these properties unique and improve synchronization with Azure AD. It all sounds like a good idea, but these properties have been around in Exchange for a long time, and any change will surface in unexpected places – like the output of many Exchange cmdlets. Which is why Microsoft has paused the plan for further reflection.

All About the Get-MailTrafficSummaryReport Cmdlet

The Get-MailTrafficSummaryReport cmdlet gets a lot of praise in some quarters. I am not so impressed. The Exchange Online cmdlet is useful, but it’s now showing its age in a world when better data to create a view of user activity is available elsewhere, notably in the Microsoft Graph. This doesn’t mean that the cmdlet doesn’t do a good job; it’s just that it hasn’t received much love from Microsoft since 2015.

Use Message Tracing to Report Exchange Online Email Sent to External Recipients

A management request came in to report email sent by some users to external recipients. Although you might not agree that this is the right thing for any organization to do, it’s very possible by exploiting the message trace information retained by Exchange Online for 90 days. As a bonus, we email the report generated from message tracing data to the requesting manager. Isn’t PowerShell just wonderful?

How to Find Unused Exchange Online Mailboxes

Finding and removing unused Exchange Online mailboxes used to be a good way to keep Office 365 licenses costs under control. Given the widespread use of Exchange Online as part of bundles like Office 365 and the effect of Teams on email for internal communication, looking for unused mailboxes might not be so important now. In any case, the techniques of looking for evidence of mailbox under-use are interesting and useful for tenant administrators to understand, which is why we have this article!

Microsoft Gives Tenants Opt-Out for Exchange Online Plus Addressing

Microsoft intends to make the Exchange Online plus addressing feature available by default to all Microsoft 365 tenants after April 17, 2022. If you don’t want this to happen, you need to update the Exchange Online organization configuration to update the DisablePlusAddressInRecipients setting to True. After the opt-out 30-day period finishes, Microsoft will proceed with the deployment, so don’t say you weren’t warned!

Why It’s Difficult to Transfer Membership Rules from Exchange Online to Azure AD

It seems like it should be possible to transfer a membership rule from an Exchange dynamic distribution list to a dynamic Microsoft 365 group/team, but it’s not. Different directories, schemas, properties. and syntax conspire to stop easy conversion. It’s a pity, but that’s the way life and technology sometimes go…

Converting Dynamic Distribution Lists to Microsoft 365 Groups and Teams

This article explains how to create a new Microsoft 365 group and team using the membership and properties of an Exchange Online dynamic distribution list. The process is reasonably straightforward, but as always with PowerShell, there are some interesting turns and twists that must be navigated en route.

Remote Connectivity Analyzer Diagnoses Teams Connections to Exchange Hybrid

Microsoft’s Remote Connectivity Analyzer (MRCA) utility is now able to run diagnostics to check connectivity between Teams and an Exchange hybrid organization. MRCA was in the doldrums for several years because no one inside Microsoft had any interest in providing funding for its development and support. Now the utility is roaring back with a set of new tests covering different aspects of Microsoft 365. Recommended!

Microsoft Delays Outlook Roaming Signatures Until July 2022

Outlook logo

Microsoft’s latest update for the roadmap item for Outlook roaming signatures puts general availability in July 2022, some two years after the original announcement. It’s a strange delay, even by the standards of the Outlook desktop development cycle. ISVs who make signature management software have used the delay to good effect to improve their products, so it remains to be seen what effect Outlook roaming signatures will have on that market.

Microsoft 365 Data Loss Prevention and Encrypted Message Type Exceptions

Microsoft 365 Data Loss Prevention (DLP) policies have wide-ranging capabilities when it comes to rules and exceptions. One exception covers the various types of encrypted email that can pass through the Exchange Online transport pipeline. As it happens, three message types are supported, but who could have guessed that permission controlled means rights management?

Keeping Confidential Outlook Email Private

Outlook logo

Delegates often process Outlook email for others. It’s a feature that works well. That is, until protected email arrives. Delegates shouldn’t be able to read protected email in other peoples’ mailboxes. But some versions of Outlook allow this to happen. If you want to be sure that delegates can’t access protected email, maybe you should consider using a dual-mailbox approach.

How Microsoft Teams Displays Local Time in User Profile Cards

A new Microsoft Teams feature means that local time zone information appears on user profile cards. While it seem simple, the feature is very useful when arranging meetings because you know up-front about the working hours of your colleagues. It’s a detail that makes sense!

Why Exchange Online Mailboxes have SharePoint Online Proxy Addresses

A post by the Exchange development group tried to explain why mailboxes have SharePoint Online proxy addresses. It’s all down to the Microsoft 365 substrate, which needs the proxy addresses to ingest digital twins from SharePoint Online into Exchange Online for use by shared services like Microsoft Search. The upshot is that you can’t remove a mailbox permanently without some background processes kicking in to make sure that SharePoint is taken care of.

The Strange Case of Outlook Desktop and Actionable Messages

Outlook desktop couldn’t display actionable messages generated by Teams and Yammer properly while OWA and Outlook mobile could. It’s a small issue in the context of Microsoft 365, but it irritated me. I fixed the problem but don’t know how except that the Actionable Messages Debugger for Outlook might have been involved. Another day in the life of a Microsoft 365 tenant administrator…

How to Protect Messages Sent to Dynamic Distribution Lists

Office 365 Message Encryption protection is not available for messages sent to dynamic distribution groups. It’s all to do with rights management licensing. However, if you need to protect messages sent to dynamic distribution groups, for instance to make sure that confidential messages are inaccessible to external recipients use a sensitivity label instead and assign the special tenant-wide permission to recipients.

How to Determine the Age of a Microsoft 365 Tenant

Finding the age of a Microsoft 365 tenant isn’t an important administrative operation. However, understanding how to retrieve this information (if asked) is an interesting question, which is why we spent several hours playing around with PowerShell and the Microsoft Graph to figure out how to answer the question. It’s the kind of in-depth analysis we do all the time to build content for the Office 365 for IT Pros eBook.

Planner Uses Exchange Online for Microsoft 365 eDiscovery and Compliance

Planner now creates digital twins (copies) of tasks in user mailboxes in Exchange Online to make data available for eDiscovery and compliance. Storing items in the Microsoft 365 substrate is the same approach to making data available for search and compliance as taken by Teams and Yammer.

Latest AAD Connect Removes On-Premises Disabled User Accounts from Azure AD

Microsoft pushed out version of the AAD Connect synchronization utility earlier this month. Unfortunately, the new software removes disabled on-premises user accounts from Azure AD, which means that on-premises shared mailboxes disappear for cloud users. Microsoft has released version but maybe it’s better to go back to a version that you know works. At least until after the holidays.

Microsoft 365 DLP Switches from Envelope to Header for Sender Evaluations

To make Microsoft 365 DLP policies work like Exchange transport-rule based DLP, a January change will switch evaluation of sender conditions away from envelope information to message headers. Although this change might seem to be something beloved of email geeks, it’s actually an important update for organizations who want to move away from ETR-based DLP to Microsoft 365 DLP policies.

How to Enable Users to Receive Copies of Email They Send to Microsoft 365 Groups

It might seem like a small thing, but some users are upset when they don’t receive copies of their messages sent to Outlook Groups in their Inbox. A new setting allows users and administrators to control if they receive copies of messages from groups, but only when the user is a subscriber to groups (Follow in Inbox is turned on). In this article, we explore how to set the EchoGroupMessageBackToSubscribedSender control via OWA options and PowerShell, and how to sign up to be a group subscriber by yourself or with a little help from an Exchange administrator.

Microsoft Upgrades Exchange Online Dynamic Distribution Lists

Microsoft is changing the way the Exchange Online transport service resolves the membership of dynamic distribution groups. Instead of doing this when someone sends a message to a dynamic group, Exchange resolves the membership once daily and whenever the recipient filter changes. It’s a reasonable approach designed to make messages move faster and more reliably, and it’s similar to the way that Azure AD dynamic groups maintain their memberships, so it shouldn’t make much difference.

Microsoft Flags Need to Upgrade PowerShell Scripts to Use TLS 1.2

Microsoft is removing TLS 1.0 and 1.1 from Microsoft 365. This has been well flagged, but tenants might not understand the impact on PowerShell scripts which send email using the Send-MailMessage cmdlet and SMTP AUTH. In a nutshell, unless you force PowerShell to use TLS 1.2, attempts to send messages via Exchange Online will fail. It’s time to check those scripts and ,consider how to move away from SMTP AUTH and Send-MailMessage.

Synchronizing Sensitivity Labels to Update SharePoint Online Sites

The SharePoint Online admin center displays an insight card for the number of unlabeled sites in the tenant. For some reason, many of the labels assigned to Microsoft 365 Groups and Teams had not reached SharePoint. Some PowerShell does the job to fetch the sensitivity label information from Exchange Online and update sites with the missing label information.

Some Microsoft 365 Features Highlighted at Fall Ignite 2021 You Can Use Now

To help you recover from the blizzard of Microsoft 365 information released at Fall Ignite 2021, here are some notes about features and functionality you might have missed. Like any list created by a conference (virtual) attendee, it reflects my interests and what I was looking for. Feel free to disagree on the importance of any or all of the topics discussed here… and suggest some of your own in the comments.

How to Use an Exchange Transport Rule to Copy Messages

Exchange Online transport (mail flow) rules are a powerful way to manipulate messages as they pass through the transport system. In this example, we look at how to BCC messages sent by some employees for management review. I’m not sure that this is a good idea (for many reasons), but the need does exist to copy messages automatically, so we explore the use of transport rules as a solution.

How Exchange Online Uses Mailbox Plans to Populate Mailbox Settings

Every Exchange Online tenant has four mailbox plans. Exchange uses the plans to populate some important mailbox settings based on the license assigned to the mailbox owner. This article explains the four mailbox plans, how to update the plan settings, and some of the things you can’t do with mailbox plans. We also include some PowerShell to report the mailbox plans assigned to users in your Office 365 tenant.

Improved DKIM Configuration Page is Prompt to Check Domains

A new Microsoft 365 DKIM management page is a good prompt to check that all domains used to send email in n Office 365 tenant are configured properly for DKIM. The process of enabling DKIM and key rotation is easily done through the GUI or PowerShell once the correct CNAME records are in DNS.

How to Use a Microsoft 365 Retention Policy to Manage Inactive Mailbox Content

Most Microsoft 365 tenants will have to manage the mailboxes of ex-employees. Retention policies are an excellent method to achieve this goal, if you remember to add mailboxes to a suitable retention policy before deleting their Azure AD account. In this article, we consider Microsoft’s recommendation to use a specific retention policy for inactive mailboxes and how to go about using such a policy.

Apple iOS Mail App Might Need Upgraded Configuration for Modern Authentication

The road to modern authentication for Exchange Online is littered with things to do. One action item is to check Apple iOS and iPad devices using Exchange ActiveSync to connect to mailboxes. If these devices were configured to connect to Exchange Online before iOS 12, they’re likely using basic authentication. Right now, the only way to move them to modern authentication is to remove Exchange from the mail app and add Exchange again. It’s a bump on the way to modern authentication in October 2022.

How to Manage Client Read Receipt Settings in OWA and Outlook for Windows

A reader request asked how to force users to send read receipts. This is a client-side feature so the settings involved differ from client to client. We explore how to control them in OWA and Outlook for Windows. A mixture of PowerShell and system registry settings help create a solution. We’re leaving figuring out how to manage other clients to our readers.

API Deprecations Signal the Demise of Exchange Web Services

A Microsoft October 5 announcement gives a clear signal that Exchange Web Services is on a short runway to oblivion. The first step is the removal of 25 APIs on March 31, 2022. It’s all part of the master plan to get Office 365 tenants and ISVs to move to the Microsoft Graph APIs. This is a perfectly laudable ambition but it’s complicated because of the lack of suitable Graph APIs to handle the volume of Exchange data involved in scenarios like backup/restore and migration. Teams has a new Graph Export API, but it introduces consumption metering and charging. Is a new Exchange API coming and will it use the same charging mechanism? We live in interesting times…

OWA Adds Full Support for Send from Proxy Address (Mailbox Aliases)

A recent update to OWA adds the option to allow users to choose which proxy addresses assigned to a mailbox they would like to send messages from. It’s a small change which completes the client support for the earlier server-side update to allow users to send using mailbox proxies, and it makes using proxy addresses more approachable and useful. OWA also includes a drop-down list in the compose message screen to allow users to select an address to send from, and makes sure that message headers are updated correctly so that messages go back to the right address.

How Microsoft Editor Can Make Your OWA Messages More Polite

A new Microsoft Editor feature aims to make OWA messages more polite through “tone detection.” Currently only available for U.S. English, Editor scans for impolite text and comes up with suggested replacement text. The results vary from very good to not so good, but this might be because it takes time for a learning model to accumulate enough information about a user’s writing style to be able to detect impolite text accurately. We’ll know over time.

How Exchange Online Uses Archives to Offload Recoverable Items Storage

A change rolling out in mid-October will remove storage pressure on the Recoverable Items structure in Exchange Online mailboxes by offloading some data to archive mailboxes. The idea is a good one because it means that the storage allocated to Recoverable Items won’t fill up and require intervention so often. Users won’t know anything about what’s happening under the covers as it’s all hidden from view.

How to Find Exchange Online Archive Mailboxes Close to the New 1.5 TB Limit

A 1.5 TB limit applies to Exchange Online archive mailboxes from November 1, 2021. In this article, we use PowerShell to report how close expandable archives are to the new limit. In reality, not many archive mailboxes will approach the new limit, but it’s nice to know things like the daily growth rate for an archive and how many days it will take for an archive to reach 1.5 TB. All whimsical stuff calculated with PowerShell!