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As 2025 begins, Microsoft is launching the automatic transition of personal and Microsoft 365 Business accounts to the “new” Outlook.
Although most users should have the ability to toggle the switch back to the “old” Outlook, it may not be that easy for everyone.
This re-designed Outlook was built to incorporate newer security protocols, integrate with Microsoft Co-Pilot AI, improve responsiveness, and provide a more modern look and feel that resembles “Outlook on the web.”
However, this new framework lacks several key features which could prove to be very problematic, especially for those in the legal industry.
Let’s dig in and explore several exciting new features that have emerged and reflect upon some of the critical functionality that is no longer available.
Features no longer available
Since its initial debut, Outlook has continued to revise the capabilities of its new structure over the last couple of years. Despite significant online backlash, there are still several crucial components that are not available.
Microsoft has not provided any clear definition as to what, if any, additional functionality is forthcoming or corresponding timeframes.
Broken integrations: Most firms have custom integrations with other 3rd party tools which allow saving emails to a document management system, syncing contacts to a CRM, tracking time in email, integrating with the case management system’s calendar, and even security and archiving tools to protect against phishing and other threats.
With the revamping of Outlook’s underlying architecture, Microsoft no longer supports “COM Add-Ins”. Consequently, the critical integrations that firms rely on to enhance the standard Outlook functionality, specifically tailored for legal needs, are no longer available
Unfortunately, this requires the other vendors to redesign their programs to align with Microsoft’s new structure and the timeline for this remains unclear.
No export option: In the legal industry, it is quite common to export Outlook data to a separate file known as a PST file as part of the discovery process and/or for archiving data. Likewise, importing PST files from other users or from old mailboxes is prevalent to see all data from a single location.
However, the “new” Outlook has really locked down these capabilities stating that “Only read-only access in the Mail module is available at this time. Other features will be added in the future.”
Therefore, it is currently not possible to export Outlook data to a PST file from the “new” Outlook or to modify a PST file that has been imported.
Quick Steps: From filing messages to a specific folder, to creating pre-addressed emails with specific content, Quick Steps have increased in popularity since their introduction over a decade ago.
Setting these automations up can save considerable time and help bolster accuracy by preventing user error in routine tasks. Unfortunately, they do not automatically transfer between the Outlook versions thus requiring users to manually recreate them in the “new” Outlook.
No QuickParts: As part of this programming overhaul, Microsoft is transitioning Outlook away from its reliance upon Word as an underlying editor.
As such the capability to create re-usable text and graphics known as QuickParts, is no longer available as part of the “new” Outlook.
Limitations of rules: Rules to automatically send certain emails to a “listserv” folder or forward emails from a specific address to other people have long been in play.
The “new” Outlook has greatly improved the interface making setting up and managing rules easier than ever, but there are now fewer options. Most of the key options are still present, but options like the ability to “play a sound” or “display a desktop alert” when certain conditions are met are no longer present.
New features
Despite the challenges listed above, the “new” Outlook features a simplified toolbar to enhance usability and introduces several enhancements too.
Sweep: The goal of Sweep is to help you clean up your mailbox as efficiently as possible. After clicking on an email from a specific person, you can click the Sweep button to choose one of the following options:
• Move all messages in the Inbox folder from that Sender to a selected folder one time.
• Move all messages in the Inbox folder from that Sender to a selected folder continuously so that it bypasses the inbox.
• Move all messages in the Inbox folder from that Sender to a selected folder continuously but leave the most recent message in the inbox.
• Move all messages older than 10 days in the Inbox folder from that Sender to a selected folder continuously but leaves most recent message in the inbox for 10 days.
Pin: Previously you may have marked important messages with a flag or category so that they did not get lost in the shuffle. Now, the “pin” function allows you to have the message moved or “pinned” to the top of the list to keep it in your line of sight until you choose to unpin it.
Scheduling poll: Rather than sending multiple emails to find times that work well for everyone, “scheduling poll” allows you to quickly select time slots from your calendar (and other internal recipients) to suggest to all recipients as a meeting time. Recipients can then vote upon the desired time slots and the sender can determine the best meeting time for everyone.
Conditional formatting: Similar to conditional formatting in Excel, you can now automatically color code emails that match specific criteria to help you visualize things in your mailbox more effectively. Conditions can include who the email is from, to, or the subject line and if the criteria is met a designated color will be used on the side of the message and for the preview font color.
Automatic responses: When automatic responses are setup, users can now choose a couple of additional options; block their calendar for that period of time to demonstrate they are out of office, and/or automatically decline any appointments sent during that period to ensure visibility to others that the person is unavailable.
Respond with emojis: In our world of “reactions” to social media posts or even text messages, Outlook now allows you to react to a message with a variety of emojis to acknowledge receipt rather than responding with a full email.
As Microsoft strives to stay current by incorporating the latest trends into Outlook, this modernization effort has regrettably come at the cost of several crucial functionalities that law firms have come to rely upon.
To ensure smooth operations, Microsoft must quickly address these critical gaps. In the meantime, utilizing Outlook.com can also give you a preview of the “new” Outlook without making any changes in your desktop application.•
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Deanna Marquez ([email protected]) is a co-owner of the Indianapolis based legal technology company, Modern Information Solutions LLC. It provides traditional IT services, software training, and litigation support specifically within the legal industry.
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