Working with Smarter O2S

Your IT team handles installation and organisation approval for the first team pilot. Employees then connect with their Outlook business account.

1. Open Smarter O2S under Apps in Outlook. Start with Outlook on the web and suitable test data.
2. If approval is missing, an authorised administrator starts Approve O2S for my organisation directly in the O2S pane. They review the standard permissions together in Microsoft’s dialog.
3. Allow the separate Microsoft window if Outlook asks. After approval, O2S automatically connects the same account and checks SharePoint and personal OneDrive. Microsoft may still require sign-in or MFA.
4. Other users choose Connect Microsoft 365 account. Organisation approval covers them too; their own SharePoint access rights still apply.

Installation, permissions and trial setup

Mail saves selected Outlook messages as EML files. A location recommendation is a suggestion — check the destination yourself.

1. Open or select the emails in Outlook. Check the selected count shown in O2S.
2. Choose a suitable location under Suggestions. Alternatively, a site favorite loads that site under Open site; choose a library or folder there.
3. Check the destination shown beside the filing action. Start filing only when the selection and destination are correct.
4. Review any duplicate or filename conflict. Open the existing match or deliberately choose an available action such as File anyway, Replace or Cancel.
5. Wait for the result. Complete any requested metadata and check the saved file through Active or Recent filings.

File selection and drag & drop prepare the same upload queue. Ready to upload means the transfer has not started yet.

1. Open the destination folder in Work in SharePoint. Choose files is the first action in the sticky document toolbar; a narrow pane shows its upload icon. You do not need to select a document.
2. Choose one or more files. Alternatively, drag files or supported Outlook emails into the open folder area — including empty space — or onto a navigation folder.
3. Under Active, check the files and each item’s destination. In Mail, any suggested email context is initially unconfirmed: only Use context copies that email’s metadata. Upload independent files without confirming that context.
4. Confirm Upload items to SharePoint. Resolve any conflicts and wait for the folder contents to refresh.
5. Complete missing required metadata in the same workspace. Standard libraries with no relevant missing required fields do not open a form.

Metadata means the additional columns in your SharePoint library, such as project number or department. The file has already uploaded when the subsequent metadata step appears.

1. If O2S automatically opens the form after upload, relevant required values are still missing. Choose the content type when several are available, then review the prefilled values.
2. Complete required fields. Scroll inside the form; More fields below indicates hidden fields. Save and Close remain accessible.
3. Open Metadata values to apply a named template or the last successfully saved values to the current or remaining drafts. Review the prefilled values before saving.
4. Save writes the current item’s values. With several files, the arrow beside it offers options for the next or all remaining items. Apply to all remaining confirms and saves the current compatible business values for those items — use it deliberately.
5. Choose Metadata values → Save as template, enter a name, then choose Save template. Using the same name updates that template. Use Metadata values → Manage templates to delete templates. Saving a template does not save the document values yet.
6. For current uploads, return to Edit metadata through Active. If only metadata saving fails, retry that step without uploading the file again.

Work in SharePoint shows documents independently of the selected Outlook email. The expanded Outlook Apps pane provides room for navigation and contents side by side.

1. Switch to Work in SharePoint, shortened to SharePoint at narrow widths. Open a site, library and folder. The folder icon beside a filing destination opens its contents in this workspace.
2. Enter at least two characters in Search this folder. Search covers the open folder; Include subfolders appears only during a search. Use Load more for additional results.
3. Clear the search term to return to folder contents. Check this list first for recent uploads because SharePoint search indexing can be delayed.
4. Select exactly one document and choose Preview, under More when needed. Microsoft 365 decides whether that file can be displayed inside O2S. Expand the Outlook Apps pane for a larger preview.
5. Use Open in SharePoint if preview is unavailable. Open and Edit in browser are separate actions; not every action supports every selection.

The bar at the bottom opens current work and successful filings. You can expand or collapse it at any time.

1. Open Active for prepared or running uploads, conflict decisions, errors and metadata work from the current session.
2. Choose Recent filings for previous successful filings. The first ten entries appear initially; Show complete history opens the rest. When no current action needs attention, the activity bar opens this tab directly.
3. Choose a filename to open the file in SharePoint. The destination opens that location inside O2S.
4. Edit metadata for current uploads through Active. For older entries in Recent filings, use SharePoint instead of the internal metadata editor.

A link, a file copy and an access grant are different actions. Check the selection, recipients and access before continuing.

1. Select the documents you need. Copy links copies SharePoint references; it does not grant additional access to other people.
2. Send links by email creates an Outlook draft with links. Attach to email creates a draft with real file copies. Review the draft and send it yourself.
3. Share can change SharePoint permissions. Choose recipients and view or edit access, review the details, and confirm only the intended grant.
4. For Share in Teams channel, check the suggested Team, choose the Channel and confirm the message. This action publishes a post only after your confirmation.
5. Send & File is a separate workflow in a compose draft: choose the destination and explicitly start that action. O2S files the current draft first and sends it only after successful filing. Do not also press the normal Outlook Send button.

In the compact pane, your profile avatar opens Help and Settings. With more space, these actions can appear directly in the header.

1. Choose automatic, light or dark appearance and check the Outlook post-filing action. Categories and destination folders come from the connected mailbox.
2. Keep the original email unchanged for initial tests. Choose a category, move, archive or delete only when that follow-up action is intended.
3. Check the displayed Microsoft 365 account before switching. Favorites, history, templates and the post-filing option are stored in your OneDrive, separated by environment, tenant and account.
4. Start the free 14-day organisation trial in O2S if none exists yet. Only the initiator confirms a contact address and the terms; product news is optional. Colleagues in the same tenant use the remaining time without another contact registration.

Read the status on the affected operation first. A successful file upload and a failed metadata step need different next actions.

1. If a site or file is missing, check access directly in SharePoint with the same account. New content may not be indexed yet; open the folder without search.
2. For connection errors, check the business account, organisation approval, popup permission, and SharePoint and OneDrive access. After successful approval, use Connect instead of granting the same permissions again.
3. For upload errors, read Active and check the destination folder before uploading again. If only metadata remains incomplete, save the metadata again without creating another file.
4. Open Help through the profile avatar for contextual topics. For support, note the short O2S error reference, time, app version, Outlook client and the steps you took.
5. Start support mode in advanced settings only when needed. Explicitly copy or download the sanitized diagnostic package, then clear it. Never send tokens, passwords or confidential email content.