Microsoft has been nudging users toward the new Outlook for a while now. If you are a NetDocuments user at a law firm, you are probably wondering what that means for saving emails and attachments. The short answer: it works, but it is different — and as of May 14, 2026, the classic Outlook experience is still ahead in at least one important area.
Here is a breakdown of both approaches so you know what you are getting into.
Classic Outlook: Two Tools, Two Jobs
In the traditional (classic) Outlook on Windows, NetDocuments gives you two separate programs:
ndSave comes bundled with ndOffice. It lets you select one or several emails and save them directly to NetDocuments. You choose where they go, navigate the folder tree, and you are done. You can also switch from saving the email itself to saving its attachments — handy when someone sends you a multi-file email, and you need all of them in a single workspace.
ndMail is the predictive layer. It monitors your inbox and suggests where to file emails based on your history and matter data. If the prediction is right, filing is a one-click operation. If it is wrong, you can override it.
You also get ndAttach for the outbound side. When composing an email, ndAttach lets you pull documents out of NetDocuments and attach them directly, keeping everything in the DMS rather than forcing you to save locally first.
These tools are installed on each computer. That means each user needs a working install, which creates some IT overhead — but it also means everything runs locally and predictably.
New Outlook: One Add-In, Cloud-Delivered
When you switch to the new Outlook, ndSave and ndMail are gone. The ndOffice ribbon disappears. In its place is the NetDocuments M365 Outlook Add-In, which is deployed through Microsoft 365 and pushed to users without requiring a per-machine installation. That is a real advantage for IT — one deployment, everyone gets it.
The add-in is under active development, and NetDocuments is regularly releasing new features. The goal is for it to eventually replace ndSave and ndMail entirely, including in classic Outlook.
Here is what it does today:
Saving emails works well. Select an email, click the NetDocuments button in the ribbon, and the add-in shows you its filing predictions. You can accept the prediction or search for a different workspace or folder. You can also select multiple emails and file them all at once. Once filed, the email gets a category tag called “ND Filed,” which you can use in Outlook rules to automatically move filed messages out of your inbox.
Sending with NetDocuments documents works too. When composing a new email, you can access your recent documents, favorites, or search NetDocuments directly. From there, you can attach documents as files, insert them as links, or deliver them as secured links. You can also convert attachments to PDF before sending, and reorder or rename them before they go out.
Saving email attachments is where the new Outlook falls short. In classic Outlook, you could switch ndSave from “email” mode to “attachment” mode and save files directly into NetDocuments as documents. In the new Outlook, that workflow does not exist in a clean, obvious way. There is no drop-down to switch modes. This is the one meaningful gap between the two experiences as of this writing.
Feature Comparison: Classic Outlook vs. New Outlook
| Feature | Classic Outlook | New Outlook |
|---|---|---|
| Saving an email | ✅ | ✅ |
| Saving multiple emails at once | ✅ | ✅ |
| Converting attachments to PDFs | ✅ | ✅ |
| Converting attachments to zip files | ✅ | ✅ |
| Renaming emails before saving | ✅ | ✅ |
| Creating a new email and adding attachments from NetDocuments | ✅ | ✅ |
| Adding document links to new emails | ✅ | ✅ |
| Adding a deliver secured link to new emails | ✅ | ✅ |
| Folder mapping | ✅ | ✅ |
| Prompt to file emails when sending | ✅ | ✅ |
| Saving email attachments directly to NetDocuments | ✅ | ❌ |
When Will You Be Forced to Switch?
This is the question I hear most often from firms using classic Outlook. The honest answer is: not as soon as Microsoft originally said — and the deadline has moved more than once.
When Microsoft first announced the transition, they set April 2026 as the date when the new Outlook would become the default for enterprise users. That date came and went. In February 2026, Microsoft pushed the opt-out phase back a full year to March 2027. That is when the new Outlook is now scheduled to become the default, but even then, users will be able to switch back to classic Outlook manually.
The current timeline looks like this:
Now through March 2027 — Classic Outlook remains the default. No forced change, no action required.
March 2027 — New Outlook becomes the default for Microsoft 365 enterprise users. Classic Outlook is still accessible, but you will need to switch back to it manually.
March 2028 (earliest) — The “Cutover” phase. After this point, users will no longer be able to revert to classic Outlook, and new Microsoft 365 deployments will only include new Outlook.
2029 — Full end of life for classic Outlook. Security updates, bug fixes, and patches stop entirely.
Given that Microsoft has already pushed these dates back once, they may push them back again. The new Outlook still has gaps — the attachment-saving limitation described above is one example — and Microsoft has acknowledged they are still working to close them before forcing the switch.
For most law firms, the practical takeaway is this: you have time, but not unlimited time. The window to evaluate the M365 add-in, identify any workflow gaps specific to your firm, and plan your transition is now, not in 2028 when you are up against a hard deadline.
Should You Switch Now?
Classic Outlook still has an edge in one area: saving attachments from incoming emails directly into NetDocuments. If that workflow is part of your daily routine, it is worth waiting for the M365 add-in to close that gap before making the switch firm-wide.
That said, if you are deploying NetDocuments to a firm that is already on the new Outlook, the M365 add-in handles email filing well, avoids the per-machine install headache, and gives administrators more firm-wide control than the classic tools ever did. NetDocuments is also still actively maintaining ndMail — version 1.17 is current as of this writing — so the classic tools are not going anywhere in the near term either.
Either way, now is a good time to open the new Outlook, install the M365 add-in, and see how it fits your firm’s workflow before the decision is made for you.
Questions about which setup is right for your firm? Schedule a consultation or contact us here.

