Set up and try Smarter O2S

You need a business Microsoft 365 account with Exchange Online, SharePoint Online and a provisioned personal OneDrive. Start the pilot in Outlook on the web. Test other Outlook clients with your IT team afterwards.

Your IT team must allow the Outlook add-in and sign-in to the hosted Smarter O2S app. Choose a SharePoint library where pilot users have write access. An existing Smarter Navigation configuration can be used; installing the add-in does not install an SPFx application.

Open the Marketplace listing using the link above. Central deployment by your Microsoft 365 administrator is recommended for teams. Personal installation from the Store is an alternative if your organization’s policies allow it.

Open an email in Outlook and choose “Smarter O2S” under “Apps”. Depending on your Outlook version, “Apps” appears in the ribbon or on the message itself. Pin the pane if you want it to stay open when switching emails.

For initial setup, an authorised tenant administrator chooses “Approve O2S for my organisation” in the Outlook pane. In an already connected app, use the profile icon → Settings → Permissions, status and diagnostics. Microsoft shows the configured standard permissions together for review. Allow the separate Microsoft window if Outlook asks.

After approval, O2S automatically connects the same business account and checks SharePoint and personal OneDrive. Microsoft may still require sign-in or MFA; this is not another approval of individual product permissions. Complete that step and wait for the O2S workspace to open.

Colleagues choose “Connect Microsoft 365 account”. The organisation approval already covers them, while their own SharePoint access rights still apply. If administrator approval is required, your IT team must complete it — repeated sign-in does not replace approval.

Installing the Outlook add-in and granting Microsoft Entra consent are separate steps. Permissions are delegated: O2S acts on behalf of the signed-in user and does not grant them additional access to other SharePoint content. The scopes are nevertheless broad and require your IT team’s review.

If your organisation has no trial yet, choose “Try free for 14 days” directly in O2S. The initiator confirms their business contact email for trial setup and evaluation, and accepts the terms and privacy notice. Additional O2S product news and tips by email are a separate, optional choice.

There is no additional sign-in on a licensing website. After starting the company trial, O2S displays the shared expiry date. Other users in the same Microsoft 365 tenant do not register another contact and use the remaining trial time. Your IT team still needs to provide the add-in and the required data access.

The fully featured 14-day trial starts with the first successful registration, not installation. Different email domains, users or reinstallation do not start a new trial. There is no automatic purchase or paid renewal. After expiry, “Contact us about Smarter O2S” leads to our contact page.

Add-in privacy policySmarter O2S terms of use

Select an email in Outlook. In “Mail”, choose a suggested location, or use “Favorites” or “Open site”. A site favorite opens its navigation; select the destination library or folder there.

Check the displayed filing location, then choose the save email action. If relevant required metadata remains empty after upload, O2S opens the form: complete the values and save. No extra input is needed when no such values are missing.

Wait for the upload to finish. Check the entry under “Active” or “Recent filings” and open the saved file. O2S then shows the filing location on the email. Categories or moving the original email depend on your settings.

Complete and save required metadata: illustrated guide

Switch to “SharePoint” or “Work in SharePoint” and open your library. The expanded Outlook pane shows navigation alongside folder contents.

Use “Choose files” to prepare local files. Alternatively, drag files or supported Outlook emails onto a destination folder or into the open workspace. Check files and destination under “Active” and confirm “Upload items to SharePoint”. Complete missing required metadata afterwards. Files in the SharePoint workspace do not inherit metadata from an unrelated email that happens to be open in Outlook.

Search the current folder. Once you enter a search term, you can include subfolders. Newly uploaded files may take time to appear in SharePoint search; check the folder list first.

Select a document to open, edit, preview or use link actions. Available actions depend on file type, selection and permissions. “Recent filings” leads to previous results. The internal metadata editor is available for current uploads under “Active”; edit older documents in SharePoint. Check recipients and access permissions before sharing content.