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Microsoft 365 Copilot Arrives in OneDrive for Windows: File Explorer AI Actions

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Microsoft’s push to fold generative AI into everyday file management just moved a major step closer to most Windows users: Microsoft 365’s Copilot is now integrated with OneDrive inside Windows, letting subscribers invoke Copilot actions from File Explorer and the OneDrive Activity Center on the taskbar as well as continuing to use the web experience. This expansion delivers inline summarization, Q&A, and multi-file comparison directly where users already manage files — and it changes how people will find, vet, and act on stored documents across personal and work accounts. (techcommunity.microsoft.com) (support.microsoft.com)

Windows desktop with floating Copilot and OneDine windows over a blue abstract background.Background​

Microsoft has been layering Copilot into its productivity stack since the initial Copilot announcement and ongoing rollouts. Copilot for OneDrive began as a web-first capability for commercial customers in late 2024 and expanded to Microsoft 365 Personal and Family subscribers in 2025 on OneDrive for the web. That web rollout introduced the now-familiar Copilot chat and file actions: summarization, Q&A, and the ability to compare multiple files. (techcommunity.microsoft.com) (techcommunity.microsoft.com)
The most recent change is important because it brings that same assistance closer to the Windows desktop: instead of switching to a browser and opening OneDrive.com, users can now access Copilot features from the File Explorer context menu and from the OneDrive Activity Center in the taskbar. This aligns with Microsoft’s broader strategy to weave AI into the Windows shell and reduce friction between context and action. Early coverage and product previews signaled Microsoft’s intention to add AI actions into File Explorer; the practical rollout makes that signal actionable for consumers with eligible Microsoft 365 subscriptions. (theverge.com)

What’s new — feature rundown​

Microsoft is bringing the following Copilot-enabled features directly into Windows for eligible Microsoft 365 subscribers who store files on OneDrive:
  • Context‑menu Copilot actions in File Explorer: Right-click a supported file, hover over OneDrive in the menu, and select Copilot actions (Summarize, Ask, Compare, Generate FAQ, etc.). This places AI assistance into the familiar right‑click workflow used for quick file operations. (theverge.com)
  • Copilot actions in the OneDrive Activity Center: From the OneDrive icon in the Windows taskbar, open the Activity Center, click the three‑dot menu next to a file, and call Copilot actions without leaving the taskbar. This provides micro-interactions for quick checks and light editing tasks. (learn.microsoft.com, support.microsoft.com)
  • Compare up to five files: Select up to five supported files and run a comparison; Copilot generates a comparison table that highlights metadata and content differences across versions or related documents. This is optimized for contract review, resume screening, quote comparison, and version reconciliation. (support.microsoft.com)
  • Summarization and Q&A: Generate short summaries, extract key points, or ask specific questions about file content (single file or combined across up to five files) and receive concise, context-aware answers. (support.microsoft.com)
  • Supported file formats: Office files (DOC/DOCX, PPT/PPTX, XLSX), new Microsoft 365 formats such as FLUID and LOOP, universal formats (PDF, TXT, RTF), certain web files (HTM, HTML), and OpenDocument formats (ODT, ODP). Note that images and videos are not currently supported for these Copilot actions. (support.microsoft.com)
These Windows surface-level integrations do not create new file types or change the underlying storage model; they simply offer Copilot’s conversational and analytic layer inside the native file management experiences that Windows users already rely upon. (techcommunity.microsoft.com)

How the UX works: practical walkthroughs​

File Explorer context menu (right‑click)​

  • Select or right‑click a supported file in File Explorer.
  • Hover over the OneDrive submenu in the context menu.
  • Choose a Copilot action: Summarize, Ask a question, Generate FAQs, or Compare files (when multiple files are selected). The Copilot panel appears and delivers immediate, actionable output.
This keeps AI interactions close to the task at hand — for example, pulling a quick executive summary for a long report or extracting negotiation points from a contract without launching Word or the browser. Early previews of "AI actions" in File Explorer anticipated this pattern and Microsoft has started shipping those micro-actions to customers with the proper Copilot entitlement. (theverge.com, learn.microsoft.com)

OneDrive Activity Center (taskbar)​

  • Open the OneDrive Activity Center via the taskbar icon.
  • Click the three-dot menu next to a specific file and select Copilot actions.
  • For lightweight workflows (e.g., checking an emailed attachment you saved to OneDrive), this avoids full app switching entirely.
Because the Activity Center sits in the taskbar, these micro-interactions can be used while staying in the middle of other work — a small but meaningful reduction in context switching. (learn.microsoft.com)

Supported file types, limits, and notable exclusions​

Microsoft’s published guidance and FAQs make clear which formats Copilot supports today and what to expect soon:
  • Supported today: DOC, DOCX, PPT, PPTX, XLSX, FLUID, LOOP, PDF, TXT, RTF, HTM, HTML, ODT, ODP. (support.microsoft.com)
  • Not supported (yet): images and videos for these Copilot file actions; folder-level Q&A is also currently unsupported. Microsoft lists planned support for images, meeting recordings and other videos, and OneNote notebooks in future updates. (support.microsoft.com)
  • File size limits: Some Copilot features are limited by file-size caps (for example, items under 150 MB for certain actions), with Microsoft stating that support for larger files is coming soon. Administrators and power users should expect these practical boundaries while the feature set scales. (support.microsoft.com)
  • Multi‑file operations: Summaries, comparisons, and Q&A actions can run over up to five files at once; Microsoft is explicit about that five‑file limit at launch. (support.microsoft.com)
These constraints matter for complex workflows: legal discovery, large-scale data analysis, and multimedia-heavy archives will still need a different workflow until broader content support and higher size limits arrive.

Enterprise and admin considerations​

Microsoft’s Copilot rollout strategy includes administrative controls and tenant-level settings that IT teams should note before enabling these capabilities across an organization:
  • Licensing and access: Copilot in OneDrive requires the appropriate Copilot or Microsoft 365 subscription (Copilot license for commercial tenants; Microsoft 365 Personal/Family entitlements for consumer usage on OneDrive web). Administrators must verify license assignments to enable broad access. (techcommunity.microsoft.com)
  • Taskbar/Copilot app policies: IT admins can pin or withhold the Copilot app from users’ Windows taskbars via the Microsoft 365 admin center and device management policies. This gives IT a lever to control exposure and adoption across endpoints. (learn.microsoft.com)
  • Permissions and compliance: Copilot respects existing Microsoft 365 and OneDrive permissions. That means users will only be able to run Copilot actions on files they can already access. For regulated environments, data governance workflows must be updated to account for AI-assisted summary and extraction operations. Microsoft also notes that Copilot honors Microsoft Purview encryption and usage rights. (support.microsoft.com)
  • Rollout cadence: Microsoft has staged the feature delivery across commercial tenants, then consumer subscribers, with stated rollouts spanning toward mid‑2025 on web and subsequent Windows integrations following as eligible Windows updates and OneDrive client versions ship. Enterprises should expect staggered availability and test in pilot groups before broad enablement. (techcommunity.microsoft.com, theverge.com)
IT teams will need to balance productivity gains with governance objectives — and plan training, acceptable-use guidelines, and logging/monitoring changes to account for Copilot‑driven interactions.

Security, privacy, and data governance analysis​

Copilot’s value depends on models that access and process user content. That raises obvious security and privacy questions that organizations and individuals should weigh carefully.
  • Permission model: Copilot actions in OneDrive honor existing file permissions and Microsoft Purview protection. If a user cannot open a file, they won’t be able to ask Copilot to summarize it. This limits some exposure but does not eliminate data‑handling concerns when broader access is granted. (support.microsoft.com)
  • Processing location and telemetry: Microsoft states that Copilot processes content in Microsoft’s cloud services. For organizations bound by strict data sovereignty requirements, administrators must verify how and where content is processed and whether any export or derivative outputs are retained in logs or telemetry. Microsoft’s documentation explains some Purview protections but organizations in regulated industries should validate compliance against legal obligations. (support.microsoft.com, techcommunity.microsoft.com)
  • Local versus cloud actions: The File Explorer and Activity Center integrations act as UI surfaces — the processing still occurs in the cloud. Users may mistakenly believe a native, local action is private; organizations should train staff that Copilot’s understanding of files requires cloud processing even when invoked via File Explorer. (theverge.com)
  • Risk of automated summaries: Summaries and Q&A can be highly useful but are imperfect. Copilot can omit nuances, misinterpret legal or financial subtleties, or produce overconfident outputs. Outputs should be treated as assistive rather than authoritative — a human verification step remains essential for critical documents. This is a core governance recommendation whenever LLMs are applied to substantive content. (support.microsoft.com)
In short: Copilot respects access controls but does not replace the need for policies, audits, and training. Organizations should update information‑handling procedures and test Copilot behavior on representative content to understand privacy implications before broad adoption.

Productivity upside — where this helps most​

The integration of Copilot into File Explorer and the OneDrive Activity Center is a pragmatic move that unlocks several productivity gains:
  • Faster triage: Quickly summarizing long reports or extracting action items saves time during triage and review, especially for busy contributors who need a rapid read of many documents. (support.microsoft.com)
  • Version and vendor comparisons: Comparing up to five files in a single view is an obvious time-saver when reconciling contract drafts, supplier quotes, or resumes. The automatically generated comparison table reduces manual inspection. (support.microsoft.com)
  • Reduced context switching: Running Copilot from File Explorer or the Activity Center reduces the need to open each file or switch to the browser, which is a small change but one that compounds across repeated tasks. (learn.microsoft.com)
  • Creative prompts from stored content: Copilot can synthesize ideas from repository files — for example, generating a draft proposal from project artifacts — which accelerates creative work and reduces the time to first draft. (techcommunity.microsoft.com)
These gains are particularly useful for knowledge workers, small business owners, and consumers managing personal documents who want to extract utility from stored files without heavy manual review.

Potential pitfalls and practical recommendations​

The feature is promising, but adoption without guardrails can create problems. The following caveats and recommendations are based on how similar AI integrations have behaved in the wild:
  • Do not treat Copilot outputs as legal or financial advice: Summaries and comparisons are aids, not replacements for expert review. Always validate Copilot conclusions in critical workflows.
  • Pilot and log: IT should pilot the integration with a subset of users and log Copilot interactions to understand usage patterns and any accidental disclosures. Use administrative controls to limit exposure initially. (learn.microsoft.com)
  • Train staff on file hygiene: Since Copilot’s power depends on accessible content, accidental retention of drafts with sensitive content can be amplified. Encourage versioning discipline and sensitivity labeling. (support.microsoft.com)
  • Beware of multimedia gaps: If your workflows rely heavily on images or video (e.g., marketing assets or meeting recordings), be aware that these are not yet handled by Copilot in OneDrive; plan alternate review flows until Microsoft adds broader media support. (support.microsoft.com)
  • Monitor cost and licensing: Copilot features can be limited to paid SKUs; organizations should project licensing and potential add‑on costs for broad internal deployment. (techcommunity.microsoft.com)

How this compares with competitors​

Microsoft’s advantage is a native, Windows-centric surface for Copilot tied directly to OneDrive and Microsoft 365 file permissions. Competitors offer their own AI integrations (for example, Google’s Workspace and Drive integrations), but Microsoft’s approach emphasizes deeper OS-level touchpoints — the right‑click menu and taskbar Activity Center — which is a differentiator for Windows users. Early reporting on File Explorer AI actions highlighted the same trend: embedding AI where people actually touch files rather than forcing a full web workflow. (theverge.com, windowscentral.com)
However, the competitor landscape is fast-moving. File support, the range of allowed actions, privacy assurances, and pricing will be the axes on which customers decide which platform best matches their needs.

What’s still unclear or evolving​

Microsoft’s documentation is comprehensive but several rollout-specific details remain fluid:
  • Exact client and OS prerequisites: The File Explorer integration will depend on Windows updates and OneDrive client versions; specifics can change as Microsoft ships new builds. Administrators should verify their environment against Microsoft’s published prerequisites before expecting universal availability. (learn.microsoft.com)
  • Timing across tenants: Microsoft has committed to staged rollouts. While commercial tenants received early access in late 2024, consumer subscribers were added in 2025, with the Windows client integrations arriving in phases thereafter. The exact schedule for any given tenant or device may differ. Treat any published rollout window as an estimate and confirm via admin portals. (techcommunity.microsoft.com)
  • Feature parity across surfaces: Some Copilot features exist on the OneDrive web experience before they appear in File Explorer or the Activity Center. Expect an initial disparity and then gradual parity as Microsoft ports the actions and mitigates technical constraints. (techcommunity.microsoft.com)
Because these are actively evolving, any claim about precise availability or capability is time-sensitive and should be re‑checked against Microsoft’s official channels before planning large deployments.

Conclusion​

Bringing Microsoft 365 Copilot into OneDrive inside Windows represents a pragmatic and meaningful expansion of AI into core productivity flows. The ability to summon summarization, ask precise questions, and compare multiple documents without leaving File Explorer or the taskbar shrinks friction in everyday workflows and will be immediately valuable to many users. However, the value depends on who has the feature (commercial vs. consumer licensing), what content is supported (text formats now; media later), and how organizations manage permissions and governance.
For Windows users and IT teams, the guidance is clear: pilot the integration, update governance and training, and treat Copilot outputs as enablement rather than final authority. When properly managed, the integration promises to turn OneDrive from a passive repository into an active productivity assistant — right where users already work. (support.microsoft.com, theverge.com)
Source: Neowin Microsoft 365 now offers deeper integration with OneDrive in Windows
 

Click to expand...
Microsoft is surfacing Copilot directly inside Windows file management: eligible Microsoft 365 subscribers can now invoke Copilot actions from File Explorer and the OneDrive Activity Center to summarize documents, ask questions, generate FAQs, and compare multiple files without opening Office or a browser. This expands Copilot from a web and app experience into the native Windows right‑click workflow, putting AI assistance where users already manage files. (support.microsoft.com)

A translucent Copilot panel with action buttons floats beside a document window on a blue UI.Background / Overview​

Microsoft has steadily woven Copilot into its productivity stack since the initial Copilot rollout, and OneDrive has been an early target for those efforts. Copilot for OneDrive first appeared as a web experience for commercial customers and later broadened to Personal and Family Microsoft 365 subscribers; the latest step brings many of those OneDrive Copilot actions into Windows itself via File Explorer context menus and the OneDrive Activity Center. This move aligns with Microsoft’s strategy of reducing context switching between the file manager, web browser, and apps, letting users get quick intelligence from files where they sit. (theverge.com)
The integration is deliberately constrained at launch: Copilot actions operate only on files stored in OneDrive and only for users with the appropriate Microsoft 365 entitlement. For now, images and videos are excluded from these actions, and multi‑file operations are limited to batches of up to five files. Those limits reflect practical constraints (format parsing, privacy, and cloud processing) and are listed explicitly in Microsoft’s OneDrive guidance. (support.microsoft.com)

What exactly you can do from File Explorer and the OneDrive Activity Center​

Microsoft exposes Copilot features through two Windows surfaces:
  • File Explorer context menu: right‑click a OneDrive‑stored file, hover over the OneDrive submenu, then select a Copilot action. This puts the interactions into the familiar right‑click workflow. (theverge.com)
  • OneDrive Activity Center (taskbar): open the OneDrive flyout from the taskbar icon, click a file’s more (three-dot) menu, and call Copilot actions without leaving the taskbar.
The main Copilot actions available in these surfaces are:
  • Summarize: generate a concise summary of a single document or up to five documents selected together. Useful for quick triage or deciding which file to open for deeper review. (support.microsoft.com)
  • Ask a question (Q&A): pose a natural‑language question and have Copilot extract the answer from a file or a small set of files. The chat panel supports follow-ups and clarifying prompts. (support.microsoft.com)
  • Create an FAQ: automatically produce a list of frequently asked questions and answers drawn from the document’s content — designed to surface the document’s notable points or recurring themes.
  • Compare files: select up to five files (supported formats only) and run a comparison that outputs a concise table of differences in metadata and content highlights — handy for contract review, version reconciliation, and vendor quote comparisons. (support.microsoft.com)
These features are delivered as Copilot “file actions” rather than by changing or reformatting files; Copilot reads file content and returns structured outputs in a side panel or lightweight UI over the file manager.

Supported file types, limits, and notable exclusions​

Microsoft publishes a list of supported formats for the OneDrive Copilot file actions. At launch, Copilot supports most text‑based productivity and web formats, including:
  • Office documents: DOC, DOCX, PPT, PPTX, XLSX
  • Microsoft 365 formats: FLUID, LOOP
  • Universal formats: PDF, TXT, RTF
  • Web files: HTM, HTML, ASPX
  • OpenDocument formats: ODT, ODP
Files types explicitly not supported yet include images, videos, and certain notebook formats. Folder‑level Q&A and very large files are also constrained. Microsoft lists a practical file‑size guideline (items under roughly 150 MB for some actions) and a five‑file maximum for multi‑file operations at launch. Expect those limits to expand over time. (support.microsoft.com)
Why this matters practically:
  • Text-heavy workflows (contracts, reports, spreadsheets) benefit immediately.
  • Media‑heavy workflows (marketing assets, meeting recordings) must wait for expanded format support.
  • Large-scale eDiscovery or bulk analysis workflows will still require dedicated tooling until higher size and file‑count limits arrive.

Licensing, account requirements, and availability caveats​

Copilot file actions in File Explorer and the Activity Center require:
  • An active Microsoft 365 subscription that includes Copilot — for consumer users this is Microsoft 365 Personal or Family; business tenants use Copilot or Microsoft 365 Copilot licensing. (support.microsoft.com)
  • The files must be stored in OneDrive (the feature surfaces only OneDrive items). (support.microsoft.com)
Notable consumer nuance: Microsoft’s FAQ states that while Copilot is included in Microsoft 365 Family subscriptions, Copilot access via OneDrive may be restricted to the subscription owner in the Family group (the billing owner) — an unexpected limitation for households that expected full multi-user parity. This is explicitly documented and worth noting when purchasing a Family plan for shared Copilot access. Treat family‑member access as a functional caveat until Microsoft updates policy or expands entitlement. (support.microsoft.com)
Availability and rollout notes:
  • Microsoft staged Copilot rollouts — commercial tenants saw early access in 2024, and consumer availability extended through 2025 on the web; the Windows client integration is being phased in as OneDrive client and Windows updates roll out. That means exact availability will vary by tenant, region, and device configuration. Administrators and consumers should not assume universal availability immediately. (theverge.com)

How the UX works in practice (quick walkthrough)​

  • Right‑click a supported file in File Explorer.
  • Hover over the OneDrive submenu in the context menu and choose Copilot > Summarize / Ask / Generate FAQ / Compare (when multiple files selected).
  • A Copilot panel opens and displays the result; follow‑up questions can be asked directly in the panel.
From the OneDrive Activity Center:
  • Click the OneDrive icon on the taskbar to open the Activity Center.
  • Click the three‑dot menu next to a file and select Copilot actions.
  • The Copilot chat interface appears; results and follow-ups operate similarly to the web Copilot experience. (support.microsoft.com)
This keeps AI interactions close to the task at hand — for example, pulling a rapid executive summary of a long report or extracting negotiation points from a contract without opening Word or OneDrive in a browser. The UX reduces context switching, which is the primary design goal for embedding Copilot into File Explorer.

Security, privacy, and governance: what IT admins and privacy‑sensitive users must know​

Copilot processes file content in Microsoft’s cloud services even when invoked from File Explorer; the File Explorer and Activity Center act as UI surfaces rather than local-only processors. That has practical governance consequences for organizations with strict data residency or handling rules. Administrators must verify processing locations, telemetry, and retention details against compliance needs. Microsoft asserts that Copilot honors existing OneDrive permissions and Microsoft Purview protection, but cloud processing still occurs and should be audited. (support.microsoft.com)
Key considerations and recommended controls:
  • Permission model: Copilot can only run on files the user has access to; it will not override OneDrive or SharePoint permissions. This reduces unauthorized exposure but does not eliminate downstream processing. (support.microsoft.com)
  • Admin controls: Enterprises can stage rollouts, control taskbar pinning, and manage which users have Copilot via admin center settings and device management policies. Use pilot groups and logging to understand usage before broad enablement.
  • Audit and logging: Record who invoked Copilot and on which files; update incident response playbooks to consider AI‑generated outputs as potential sources of data leakage if misused.
  • Human review: Treat Copilot outputs as assistive, not authoritative — especially for legal, financial, or regulated content. Automated summaries can omit nuance or misrepresent subtle contractual language.
Caveat: Microsoft’s documentation is good on permission handling but less explicit about which processing steps may fall back to global cloud endpoints vs. localized regional services; organizations with strict data residency requirements should validate mappings with Microsoft support or account teams. Flag this as an area requiring direct verification for regulated deployments. (support.microsoft.com)

Practical use cases where Copilot in OneDrive will help immediately​

  • Rapid triage of long documents: executives, paralegals, and program managers often need a quick read of many files; one‑click summarization saves hours of manual scanning.
  • Contract and vendor comparisons: the Compare feature produces a side‑by‑side table of differences across up to five files, making it easy to spot changed clauses, dates, or authors. (support.microsoft.com)
  • Resume screening and hiring: initial candidate triage across multiple resumes (up to five at a time) can highlight experience, dates, and role matches quickly.
  • Data extraction from mixed documents: ask Copilot specific questions across a selection of files (e.g., “Which proposals include pricing for service X?”) and get extracted answers without manual collation. (support.microsoft.com)
  • Household productivity: personal users can summarize bills, extract action items from scanned documents, or produce an FAQ from a long instruction manual — though remember family‑plan entitlement nuances. (xda-developers.com, support.microsoft.com)

Limitations, likely friction points, and where Microsoft will need to improve​

  • Media and notebook support: images, video meeting recordings, and OneNote notebooks are not supported at launch for OneDrive Copilot file actions. Users with media-heavy workflows will need alternative review methods. Microsoft lists media support as “coming soon.” (support.microsoft.com)
  • File size constraints: actions are constrained by pragmatic size limits today (examples include ~150 MB boundaries) and may fail on larger files until Microsoft adjusts resource handling. This matters for long reports with embedded media or high‑resolution PDFs.
  • Privacy assumption risk: File Explorer integration may create a false expectation that the action is entirely local. The UI should do more to surface where processing happens; IT teams must train users accordingly.
  • Family subscription restrictions: the Family plan access limit (owner‑only) may surprise consumers who expect all Family members to share Copilot privileges. That will likely be a customer friction point until Microsoft changes entitlements. (support.microsoft.com)
  • Edge cases in comprehension: LLM‑based summaries can omit nuance, misinterpret ambiguous phrasing, or hallucinate specifics; for critical tasks, human verification remains essential.

Admin checklist: steps to prepare for controlled rollout​

  • Inventory: identify locations and file types that will be frequently analyzed by Copilot (contracts, proposals, resumes).
  • Pilot: enable Copilot actions for a small pilot group to observe behavior and surface policy gaps.
  • Permissions review: confirm OneDrive and SharePoint sharing settings and Purview labels are applied consistently to sensitive data.
  • Logging: enable detailed auditing for Copilot actions and integrate logs into SIEM for review.
  • Communication: warn users that Copilot processing occurs in the cloud and that outputs are assistive; establish verification rules for legal/financial items.
  • Policy updates: update acceptable‑use and data‑handling policies to include AI interactions and derived outputs.

How Microsoft’s approach compares to competitors​

Microsoft’s primary advantage is deep integration with Windows and Office workflows: embedding Copilot into File Explorer and the taskbar turns the file manager into an AI surface. That reduces friction relative to competitors that keep AI functionality confined to web apps or separate assistant products. Competitors like Google Workspace are also adding AI features to Drive and Docs, but Microsoft’s OS‑level touchpoints (right‑click and taskbar) are a unique differentiator for Windows users. The comparative axes that will matter to buyers are file support, privacy/processing guarantees, enterprise controls, and overall pricing. (theverge.com)

Verified technical claims and cross‑checks​

  • Multi‑file limit: Copilot file actions support up to five files at once. This is documented in Microsoft’s OneDrive guidance. (support.microsoft.com)
  • Supported formats: Office (DOC/DOCX/PPT/PPTX/XLSX), FLUID/LOOP, PDF/TXT/RTF, HTM/HTML/ASPX, and OpenDocument (ODT/ODP) are supported; images and videos are not supported at launch. See Microsoft’s FAQ. (support.microsoft.com)
  • Licensing: Microsoft 365 Personal and Family subscribers have Copilot access for OneDrive; Family plan access may be limited to the subscription owner. Business customers use Copilot licensing for commercial tenants. Microsoft’s support pages state these requirements. (support.microsoft.com)
  • File Explorer UX: The right‑click → OneDrive → Copilot actions workflow is described in Microsoft’s rollout materials and corroborated by press coverage of the File Explorer AI actions. (theverge.com)
These claims were cross‑checked against Microsoft support pages and independent reporting to ensure accurate, verifiable descriptions of features and limits. When Microsoft’s documentation was intentionally vague (for example, precise data center locations used for processing or exact rollout dates by tenant), this article flags those items as needing direct verification for compliance or planning. (support.microsoft.com, theverge.com)

Practical examples and micro‑workflow suggestions​

  • Finding the gist of a long report: right‑click the Word/PDF file and choose Copilot > Summarize to get an executive summary and action items. Use the chat follow‑ups to extract specific data points or page references.
  • Comparing vendor quotes: select up to five quote documents and run Compare files; export the comparison insights into a short email or checklist to speed procurement decisions. (support.microsoft.com)
  • Creating a short FAQ from a manual: run Generate FAQ on a technical spec or user manual to produce a consumer‑friendly Q&A that can be republished as a knowledge base entry (with human edits).
  • Resume triage: summarize candidate resumes in batches of up to five to produce short profiles you can move into an applicant tracking workflow.

Risks and recommended mitigations — summarized​

  • Risk: accidental upload/processing of sensitive files. Mitigation: enforce strict sharing controls, apply sensitivity labels, and restrict Copilot access for sensitive groups.
  • Risk: over‑reliance on AI summaries for legal/financial decisions. Mitigation: require human verification and designate Copilot output as "assistive draft" in workflow documentation.
  • Risk: tenant exposure due to misconfigured sharing. Mitigation: conduct entitlement audits before wide rollout and use pilot groups.
  • Risk: consumer confusion over Family plan entitlements. Mitigation: communicate subscription limitations clearly to users and consider Individual licenses for household power users. (support.microsoft.com)

Where Microsoft needs to earn trust and what to watch for next​

  • Expanded format support: adding images, meeting recordings, and OneNote notebooks will materially increase Copilot’s utility for many teams. Track Microsoft updates for expanded media support. (support.microsoft.com)
  • Better transparency on processing: clearer UI signals showing when content is being uploaded, where it’s processed, and whether outputs are retained would reduce misunderstandings.
  • Family‑plan parity: revising the Family entitlement model would remove a common consumer friction point and simplify purchasing decisions. (xda-developers.com)
  • File size and scale: raising file size limits and increasing the number of files handled in a single operation will unlock enterprise scenarios such as bulk contract review and deeper archival analysis.

Final analysis: productivity potential balanced with governance responsibility​

Embedding Copilot directly into File Explorer and the OneDrive Activity Center is a pragmatic step that lowers friction for everyday productivity tasks. For knowledge workers, small businesses, and power users, the ability to summarize, compare, and query documents without leaving the file manager is an immediate productivity win. Microsoft’s design places AI where files are already handled, which is likely to change routine workflows and accelerate decision cycles for many users.
That upside comes with measurable governance responsibilities: cloud processing, format limitations, family subscription nuances, and the imperfect nature of large‑language‑model outputs require IT controls, user training, and conservative adoption for regulated content. Organizations should pilot conservatively, log interactions, and update policies to incorporate AI interactions as first‑class elements of their information governance programs.
Microsoft’s documentation and independent reporting agree on the core capabilities and constraints, but rollout timing and some processing‑location details remain fluid and should be verified for high‑risk deployments. Where Microsoft is explicit, the limits are reasonable and well documented (five‑file cap, supported formats, owner‑only Family entitlement). Where Microsoft is vague, treat claims as provisional and validate directly with Microsoft support for compliance programs. (support.microsoft.com)
Bringing Copilot into OneDrive and the Windows file manager is an important evolution in how AI assistants integrate with OS workflows: powerful, immediately useful for text‑centric work, and governed by clear constraints that administrators and users must respect. The next six to twelve months will determine whether Microsoft expands format support, relaxes limits, and tightens transparency enough to make Copilot a trusted, day‑to‑day assistant across both business and consumer OneDrive usage.
Source: xda-developers.com Microsoft 365 subscribers are getting a new tool to help them get more from their OneDrive files
 

Microsoft has quietly moved a major piece of its AI productivity stack out of the browser and into the Windows shell: eligible Microsoft 365 subscribers can now invoke Copilot file actions directly from File Explorer and the OneDrive Activity Center, letting users summarize documents, ask targeted questions, generate FAQs, and compare multiple files—without opening a single Office app or a browser window. (support.microsoft.com)

Futuristic Copilot holographic UI connected to the cloud with floating panels.Background​

Microsoft has been integrating Copilot into the Microsoft 365 ecosystem since the broader Copilot rollout began, and OneDrive has been a priority surface for those efforts. The OneDrive web experience received Copilot features earlier in 2024–2025; the recent change brings many of those same capabilities into Windows itself by exposing Copilot as an action you can call from the file manager and the OneDrive taskbar flyout. This reflects Microsoft’s strategy to reduce context switching and deliver intelligence directly where files are managed. (techcommunity.microsoft.com)
Microsoft’s documentation and product posts make one point especially clear: the new File Explorer and Activity Center integrations are UI surfaces rather than local processors—the heavy lifting happens in Microsoft’s cloud services even when you launch Copilot from the desktop. That distinction matters for compliance, governance, and user expectations. (support.microsoft.com)

What’s new: Copilot actions inside Windows​

The rollout places Copilot-controlled, file-specific actions into two Windows surfaces:
  • File Explorer context menu: Right‑click a supported file stored in OneDrive, hover over the OneDrive submenu, and choose from the Copilot action list.
  • OneDrive Activity Center: Click the OneDrive icon in the taskbar to open the Activity Center, use the three‑dot menu next to a file, and call Copilot actions without leaving the taskbar.
These micro-interactions are intentionally lightweight: the UI opens a Copilot panel or chat-like overlay and returns structured outputs—summaries, Q&A answers, generated FAQs, or comparison tables—so you can act on a file quickly and return to work.

The core actions available​

  • Summarize — Quickly produce a short, human-readable summary of a single file or a small batch (up to five files). Ideal for triage or rapid review.
  • Ask (Q&A) — Pose natural-language questions and receive answers extracted from file content; the Copilot chat supports follow-ups.
  • Generate FAQ — Automatically create a list of frequently asked questions and answers drawn from a document’s content to help knowledge-base creation.
  • Compare files — Select up to five files and get a concise comparison table highlighting metadata and content differences (exclusive to the File Explorer multi-select flow). This is particularly useful for contract review, quote comparisons, or resume triage.

Supported formats, limits, and current exclusions​

Microsoft’s support documentation lists the file types supported at launch and some practical limits to keep in mind:
  • Supported text and productivity formats include DOC/DOCX, PPT/PPTX, XLSX, FLUID, LOOP, PDF, TXT, RTF, HTM/HTML/ASPX, ODT, and ODP. Images and videos are explicitly not supported for these Copilot file actions yet.
  • Multi-file operations (Summarize, Compare, Q&A) are limited to up to five files per action at launch.
  • Microsoft indicates practical file-size guidance (for example, many actions target items under roughly 150 MB), with support for larger or more complex files planned over time. This means extremely large PDFs, archives, or media-rich files may be rejected or truncated.
These constraints reflect current parsing, network, and compute tradeoffs: text-based documents are straightforward to ingest and summarize, while images, videos, and some notebook formats require different processing pipelines and are therefore scheduled for later support.

Practical workflows and real-world use cases​

Embedding Copilot into File Explorer changes the mental model of how you approach files. Instead of opening documents to inspect them, you can get the gist and extract action items directly from the file list. Here are practical examples:
  • Rapid executive triage: right‑click a long report (Word or PDF) → Copilot > Summarize → review executive summary and action items in the side panel. This saves time when you must review many documents quickly.
  • Contract comparison: select multiple contract drafts → Copilot > Compare → receive a side‑by‑side table showing changed clauses, dates, and authors. Ideal for legal or procurement teams during redline review.
  • Resume screening: batch up to five CVs, run Summarize or Compare to extract role matches, dates, and highlights—useful for first-pass triage.
  • Knowledge base creation: run Generate FAQ on a long manual or spec to accelerate the production of user-facing help articles (with human editing).
These micro-workflows are not just convenience features; they alter the balance between finding information and processing it. The less time spent opening files, the more time you have for decision-making and follow-up actions.

Licensing, account requirements, and availability​

To use Copilot file actions from File Explorer or the Activity Center you must meet a few conditions:
  • Be signed into Windows with your Microsoft account that has an active Microsoft 365 subscription that includes Copilot access. For consumer users, Microsoft lists Microsoft 365 Personal and Microsoft 365 Family as the entry points for OneDrive Copilot on consumer plans; commercial tenants require the appropriate Copilot licensing.
  • The file(s) must be stored in OneDrive. Copilot file actions in File Explorer are surfaced only for files that OneDrive manages and for files accessible under the signed-in account.
  • For Microsoft 365 Family, be aware there are entitlement nuances: the Family subscription owner (billing owner) may have different access rules than other family members; Microsoft’s guidance documents call this out as an area to confirm before assuming full multi-user parity. This is a consumer caveat worth noting when purchasing shared plans.
Rollouts are staged by tenant, region, and client version: commercial customers and Windows Insiders saw earlier access, while consumer availability has followed. Do not assume immediate global availability on every machine; the OneDrive client and Windows update cadence will govern when features appear.

Security, privacy, and governance implications​

Because Copilot’s file actions process content in Microsoft’s cloud, invoking Copilot from File Explorer or the Activity Center has non-trivial governance implications.
  • Processing location: Microsoft documents that Copilot processes file content in Microsoft cloud services even when called from the desktop UI. That means enterprises with strict data residency or sovereignty constraints must validate where content is processed and whether it meets regulatory requirements. Microsoft’s documentation affirms adherence to OneDrive permissions and Microsoft Purview protections, but it is intentionally less explicit about precise data center endpoints used for particular tenants—an area that requires direct verification for regulated deployments. Treat this as a verification point for compliance teams. (support.microsoft.com)
  • Permission model: Copilot respects OneDrive and SharePoint permissions—users cannot summarize or query files they don’t already have access to. That lowers the risk of accidental exposure but does not remove cloud processing from the privacy equation.
  • Auditability and logging: Administrators should expect to capture who invoked Copilot and on which files. Microsoft provides admin controls to stage rollouts and manage feature exposure, but governance playbooks must be updated to account for AI-assisted summaries as potential sources of leaked or misinterpreted content.
  • Output fidelity: Automated summaries and extracted answers are assistive, not authoritative. Copilot can omit nuance, misinterpret legal or financial subtleties, or provide overconfident answers. For sensitive content, human review remains mandatory.
Recommended administrative controls include pilot programs, tenant-level policy gating, entitlement audits, sensitivity labels for sensitive document classes, and explicit user training that clarifies the cloud-processing model and the assistive nature of outputs.

Limitations, friction points, and areas that need clarity​

The feature is useful today but has several practical limitations and open questions:
  • Media not supported yet: images, videos, meeting recordings, and OneNote notebooks are not supported by the Copilot file actions in File Explorer. That excludes an entire class of media-rich workflows—for now.
  • File-size ceilings: some actions show soft limits (e.g., ~150 MB guidance). Large files may be truncated or refused; Microsoft intends to expand size limits but hasn’t published a firm schedule. Users working with large reports or scanned archives should test representative files.
  • Family subscription nuance: Family-plan entitlements may be restricted to the subscription owner for some Copilot features in OneDrive; households should validate access before relying on shared Family plans for Copilot workflows.
  • Processing transparency: Microsoft’s public docs explain that content is processed in the cloud and that Purview protections apply, but they do not always map processing to specific geographic endpoints or provide a simple UI indicator for where a particular file is processed. Organizations with strict sovereignty requirements should validate with Microsoft directly. This is a known gap and should be treated as such.
Where documentation is intentionally vague—especially about data center routing and telemetry retention—treat those items as unverifiable without a tenant-level discussion with Microsoft or support contracts. Flag these explicitly in privacy assessments and procurement negotiations.

Enterprise admin checklist​

  • Verify licensing: confirm which users have Copilot entitlement under your tenant and whether consumer Family/Personal accounts in mixed environments require different handling.
  • Pilot in small groups: roll out to a controlled set of users and gather telemetry on usage patterns, file types, and any unexpected behavior.
  • Update governance docs: add Copilot invocation to data-handling procedures and incident-response playbooks; ensure outputs are marked as “assistive.”
  • Establish logging and auditing: ensure Copilot invocations are recorded and accessible for compliance reviews.
  • Test with representative content: validate behavior on large files, mixed-format batches, and files with sensitivity labels to confirm expected handling.

Competitive context: why Windows-level integration matters​

Embedding AI actions into File Explorer gives Microsoft a unique OS-level advantage versus cloud-first competitors. While Google Workspace is adding AI features to Drive and Docs, Microsoft’s approach ties Copilot directly into the Windows shell—right‑click and taskbar actions that many users will find discoverable and natural. That OS integration can convert casual users into habitual Copilot users because the friction of opening a browser or loading an app disappears.
However, the advantage is conditional: it hinges on OneDrive adoption and Copilot licensing. For users or organizations that prefer alternative cloud storage providers or limited cloud processing, Google’s or third-party workflows might remain preferable. The strategic play is clear: Microsoft is making Copilot an invisible productivity layer across OS, web, and apps to lock value into its platform.

Hands-on tips for power users​

  • Keep OneDrive synced and signed in: Copilot actions appear only for items OneDrive manages and for the signed-in account. Maintain an up-to-date OneDrive client to see the latest UI.
  • Use multi-select deliberately: selecting up to five files and running Compare or Summarize can replace early-stage manual aggregation work. Use this when you need a quick reconciliation rather than a detailed legal read.
  • Treat outputs as drafts: copy Copilot-generated summaries and FAQs into a local document for human editing before sharing externally. This preserves provenance and allows traceability.
  • Sanitize sensitive content: remove or redact personally identifying or regulated data before invoking Copilot actions if you lack clear internal policies about cloud processing.

What to watch next​

Microsoft has scheduled a OneDrive digital event on October 8 titled “Copilot + OneDrive — Intelligence in every click, inspiration in every memory” where the company plans to showcase OneDrive’s latest AI innovations and roadmap items. Expect deeper demos, expanded media support timelines, and possibly clearer enterprise guidance about processing locations. Organizations and curious users should watch that presentation for concrete timelines and feature previews. (techcommunity.microsoft.com)
Also watch for these specific updates in the months ahead:
  • Expanded support for images, meeting recordings, and OneNote notebooks (explicitly called out as planned in Microsoft materials).
  • Broader file-size limits and multi-file batch increases as backend processing scales.
  • UI transparency improvements that explicitly indicate when a file is being uploaded or processed and where that processing occurs—an important trust-building move for enterprise customers.

Final analysis: strengths, risks, and the pragmatic verdict​

The integration of Copilot actions into File Explorer and the OneDrive Activity Center is a significant usability win. It reduces context switching, shortens triage workflows, and surfaces AI functionality where users already spend time managing files. For text-heavy, knowledge-worker tasks—contracts, reports, and spreadsheets—this is immediately valuable and can save hours per week for heavy users.
However, the move is not risk-free. The two biggest practical concerns are:
  • Cloud processing and governance—Copilot actions upload file content for cloud processing, which raises policy, data residency, and auditability questions that enterprises must address before broad adoption. Microsoft’s documentation provides guidance but lacks some tenant-level specifics that compliance teams will want to verify.
  • Feature and entitlement friction—format support gaps (images, video), size limits, and Family-plan entitlement nuances mean some user scenarios won’t benefit yet. Treat this as a staged productivity uplift, not a universal replacement for deeper review or specialized tools.
Pragmatically, deploy this technology as an assistive layer: pilot with non-sensitive content, update governance policies, and require human validation for legally or financially consequential documents. For consumers, the experience is instantly useful for personal productivity tasks—bills, manuals, and quick research—but households should confirm Family-plan access nuances before making Copilot the default method for shared content.
The bottom line: Copilot file actions in File Explorer make the promise of ambient, context-aware AI tangible for everyday Windows users. They deliver clear productivity gains today while leaving important governance and scope questions to be solved. For IT teams and privacy-conscious users, careful piloting and explicit verification of processing guarantees remain essential before broad enablement. (support.microsoft.com)
Conclusion: Microsoft’s OneDrive Copilot actions in Windows represent a natural next step in the company’s effort to weave AI into the productivity surface. The feature will save time for many users and will likely accelerate adoption of Copilot across Microsoft 365—but realizing its full potential responsibly requires attention to licensing, governance, and the incremental expansion of supported formats and size limits. (techcommunity.microsoft.com)
Source: Windows Report Microsoft 365 users get Copilot actions for OneDrive files in File Explorer
 

Microsoft’s Copilot is no longer just a chatbox in the browser — it’s now an active assistant inside OneDrive and the Windows file manager, able to summarize documents, answer questions, generate FAQs, and compare up to five files at once, all without opening Office apps. (support.microsoft.com)

Windows desktop showing OneDrive UI with a Copilot panel on the right.Background / Overview​

Microsoft has steadily moved Copilot from a siloed web experience into the heart of Windows and Microsoft 365 workflows. What began as Copilot features on OneDrive for the web has expanded into Windows surfaces — notably the OneDrive Activity Center (taskbar flyout) and the File Explorer context menu — so users can call AI actions where they already handle files. That shift is intentional: reduce context switching, speed triage, and make everyday document tasks (summaries, Q&A, comparisons) a one‑click operation. (techcommunity.microsoft.com)
Microsoft’s official help pages list the core capabilities now available to Microsoft 365 subscribers with Copilot entitlements: summarize files (single or up to five together), ask questions across file contents, generate FAQs from documents, compare up to five files and produce difference tables, and create audio overviews for certain commercial customers. The company explicitly notes these actions operate on files stored in OneDrive and that the desktop integrations are UI surfaces — processing still occurs in Microsoft’s cloud. (support.microsoft.com)

What’s new: Features and how they work​

Summaries, Q&A, and FAQs — fast content triage​

  • Summarize your files: Copilot can produce concise summaries for Word documents, PowerPoint decks, spreadsheets, PDFs and other supported text formats, saving you the time of opening and scanning large documents. Summaries can be run on a single file or up to five selected files together for a combined overview. (support.microsoft.com)
  • Ask about your files (Q&A): A chat-style panel lets you ask natural-language questions — for example, “what are the action items in this report?” or “which vendor offers the shortest timeline?” — and Copilot extracts answers from the content. The chat supports follow-ups and clarifying prompts. (support.microsoft.com)
  • Generate an FAQ: Copilot can automatically create a list of frequently asked questions and answers derived from a file’s contents — useful for creating quick knowledge-base entries or onboarding materials. (techcommunity.microsoft.com)
These capabilities are designed for rapid triage: executives, legal reviewers, hiring managers, and project leads can get the gist of long documents without manual review. Early testing and product documentation stress the assistive nature of these outputs — they are starting points, not authoritative legal or financial analyses.

File comparisons — up to five files at once​

The Compare feature is a standout for version reconciliation and vendor/quote hunting. Select up to five supported documents (Word, Excel, PowerPoint, PDF and others), invoke Copilot’s Compare action, and the assistant produces a concise comparison table highlighting differences in metadata (author, last modified), content summaries, dates, and other key fields. This is explicitly limited to a maximum of five files per comparison at launch. (support.microsoft.com)

Where to invoke these actions​

  • File Explorer (Windows): Right‑click a OneDrive-stored file, hover over the OneDrive submenu, and choose Copilot actions (Summarize, Ask, Generate FAQ, Compare for multi-select). The UI opens a Copilot panel anchored to the file manager.
  • OneDrive Activity Center (taskbar): Open the OneDrive flyout and use the file’s three‑dot menu to call Copilot actions without leaving the taskbar.
  • OneDrive (web): Copilot remains available on OneDrive.com through the Copilot button and command bar. Some capabilities were first rolled out on the web and may appear there slightly earlier. (support.microsoft.com, techcommunity.microsoft.com)

Supported file types and current exclusions​

At launch, Copilot's OneDrive file actions explicitly support a broad set of text-centric formats:
  • Office formats: DOC, DOCX, PPT, PPTX, XLSX
  • Microsoft 365 formats: FLUID, LOOP
  • Universal text formats: PDF, TXT, RTF
  • Web files: HTM, HTML, ASPX
  • OpenDocument: ODT, ODP
Not supported (yet): images, screenshots, and videos for these file actions — audio-overview features have separate coverage and are initially targeted to commercial customers for specific file types. There are also practical file-size boundaries for certain actions (for example, Microsoft guidance mentions a rough guideline near ~150 MB as a practical constraint for some operations). (support.microsoft.com)

Step-by-step: Using Copilot file actions in practice​

Below is a practical walkthrough to use these features from Windows and OneDrive Web.
  • Ensure the file(s) you want to analyze are stored in OneDrive and that you are signed in with a Microsoft 365 account that includes Copilot entitlements (Personal, Family with some caveats, or a Copilot commercial license). (support.microsoft.com)
  • From File Explorer:
  • Right‑click a supported file stored in OneDrive.
  • Hover over the OneDrive submenu and select Copilot > Summarize / Ask / Generate FAQ. For comparisons, multi-select up to five files, then select Copilot > Compare files.
  • From the OneDrive Activity Center:
  • Click the OneDrive icon in the taskbar.
  • Find the file and click the three‑dot menu next to it.
  • Choose the Copilot action you want and watch the Copilot pane open for results and follow-ups.
  • From OneDrive Web:
  • Sign into OneDrive.com and select files (up to five).
  • Use the Copilot button on the command bar or the More actions (...) menu > Copilot > [action]. (support.microsoft.com)
  • Tips for better results:
  • Be specific in your prompts (e.g., “List the three most important contract clauses that change payment terms” rather than “summarize”).
  • When comparing files, note that Copilot highlights metadata and content snippets but will not replace a line-by-line legal review.
  • For multi-file Q&A, provide context (project name, date range) so Copilot can prioritize relevant content. (support.microsoft.com)

Licensing, availability, and rollout caveats​

Copilot file actions require an eligible Microsoft 365 license. Commercial customers with Copilot licenses saw early access, and Microsoft has been rolling consumer availability to Microsoft 365 Personal and Family subscribers, with the Windows client integrations distributed via OneDrive and Windows updates. Availability can vary by tenant, region, and device configuration, so organizations should not assume immediate universal rollout. (techcommunity.microsoft.com, support.microsoft.com)
A notable consumer nuance: Microsoft’s documentation indicates that Copilot in OneDrive may be limited to the subscription owner for Microsoft 365 Family plans, meaning other family members might not automatically have the same Copilot access. This is an important buying and deployment consideration for households expecting full parity. Administrators and purchasers should verify entitlement mappings in the Microsoft 365 admin center before assuming access. (support.microsoft.com)

Security, privacy, and governance implications​

Embedding AI where files are stored is powerful, but it raises concrete governance questions. Microsoft is clear that Copilot processes files in the cloud even when invoked from File Explorer — the desktop surfaces are UI entry points only. That cloud processing model has critical implications for regulated environments, data residency, and telemetry. (support.microsoft.com)
Key considerations:
  • Processing location and data residency: Organizations with strict residency requirements must confirm where content is processed and whether any derivative outputs or telemetry are retained centrally. Microsoft documents Purview protections and permission models, but some processing-location specifics can be tenant- and region-dependent; verify with Microsoft account teams where necessary. (support.microsoft.com)
  • Permission model and access controls: Copilot respects OneDrive and SharePoint permissions — users can only run Copilot on files they already have access to. That mitigates unauthorized exposure but does not eliminate the fact that content will be handled by cloud models. Admins should treat Copilot interactions as potentially audited events.
  • Audit, logging, and detection: Organizations should add Copilot interactions to their logging and incident response playbooks. Consider logging who invoked Copilot, which files were involved, and the timestamps of interactions. This becomes particularly important in regulated industries and for eDiscovery.
  • Human-in-the-loop validation: Summaries and automated comparisons are assistive. For legal, financial, clinical, or other high-stakes content, outputs should be verified by appropriate subject-matter experts before decisions are made. Several advisories emphasize that Copilot outputs can omit nuance or be overconfident.
  • Family and shared accounts: Family-plan entitlement details may restrict who in a household can run Copilot; treat family-sharing expectations carefully when sensitive content is involved. (support.microsoft.com)
Practical admin steps:
  • Use pilot groups and progressive rollout policies (staged enablement).
  • Configure logging to capture Copilot interactions for auditing.
  • Apply DLP and sensitivity labels to files to control which content is eligible for Copilot processing.
  • Update acceptable-use and information-handling policies to include AI-assisted operations.

Strengths: Where Copilot in OneDrive shines​

  • Faster triage and decision cycles: Busy knowledge workers can get key points from long reports or multiple resumes in seconds rather than minutes or hours. The right‑click integration removes friction and reduces context switching.
  • Convenient multi-file comparison: The five-file Compare action is specifically useful for contracts, vendor quotes, and resume screening — scenarios that previously required manual side-by-side checks or third-party tools. (support.microsoft.com)
  • Integration with existing permissions: Because Copilot respects OneDrive permissions, it ties into existing access controls rather than creating new ones, simplifying governance in environments already standardized on Microsoft 365.
  • Broad set of supported text formats at launch: Support for Office, PDF, OpenDocument, and common web/text formats covers many enterprise and consumer text workflows today. (support.microsoft.com)

Risks and limitations: What to watch closely​

  • Cloud processing is unavoidable: The desktop right‑click feel can mask the fact that file content is sent to cloud services for analysis — a distinction that matters for data sovereignty, regulated content, and privacy. Users could mistakenly assume processing happens locally.
  • No image/video support yet: If your workflows depend heavily on multimedia (marketing assets, meeting recordings, screenshots), Copilot’s OneDrive file actions won’t help until Microsoft extends format support. That limits applicability for many creative teams. (support.microsoft.com)
  • File-size and batch limits: The five-file cap and practical size boundaries limit bulk use cases like mass contract review or large-scale discovery. Expect these limits to be raised over time, but plan around them for now.
  • Entitlement and licensing complexity: Copilot access is tied to paid SKUs and tenant settings. Family-plan oddities and commercial license add‑ons mean organizations must plan licensing budgets and entitlement mapping before broad deployment. (support.microsoft.com)
  • Overtrust and hallucination risk: Like all large language model tools, Copilot can occasionally hallucinate or omit critical detail; treat outputs as assistive and validate them in critical workflows.

How Copilot in OneDrive compares with competitors​

Microsoft’s main advantage is the depth of integration with Windows and File Explorer — AI actions exposed via the right‑click menu and taskbar flyout are unique selling points for Windows-centric organizations. Competitors such as Google Workspace and Drive offer AI features in their own ecosystems, but Microsoft’s OS-level surfaces and existing enterprise management tooling (Microsoft 365 admin controls, Purview) give it a strong position for enterprises already standardizing on Windows and Microsoft 365. That said, the competitor landscape is fast-moving; file support, privacy assurances, and pricing will be the deciding factors for many customers. (theverge.com, computerworld.com)

Recommendations for IT teams, power users, and consumers​

For IT teams​

  • Run a pilot (small group) and log all Copilot interactions.
  • Validate processing locations and compliance mappings with Microsoft for regulated data.
  • Apply sensitivity labeling and DLP rules to restrict Copilot access to highly sensitive content.
  • Update acceptable‑use policies and training to reflect AI-assisted workflows.

For power users and knowledge workers​

  • Use Copilot for fast triage and idea generation, but keep human verification on critical outputs.
  • When comparing contracts, use Copilot to spot differences, then perform a detailed legal review for any change that matters.

For consumers and families​

  • Check Microsoft 365 Family entitlement details if you expect multiple household members to use Copilot — don’t assume parity with the subscription owner.
  • Be mindful of what you store in OneDrive if you want to avoid cloud-based AI processing of certain documents. (support.microsoft.com)

What’s still evolving — and what to verify before broad adoption​

Microsoft’s documentation is comprehensive about what Copilot can do today, but several items remain fluid and should be verified for high‑risk or large deployments:
  • Exact rollout timing for Windows client integrations: the OneDrive client and Windows updates will ship in stages; availability may differ by tenant, region, and device OS build. Confirm schedules in your admin portals.
  • Processing-location details for specific tenants and regions: ask Microsoft support or your account team for explicit mappings if data residency is a compliance requirement.
  • Planned format expansions and file-size limits: Microsoft has signalled future support for images, meeting recordings, and OneNote notebooks; treat these as planned rather than guaranteed until published in official release notes. If you rely on those formats, track product updates closely.
Flag any claim about future or expanded behavior as provisional until you see a concrete Microsoft update or admin center notice; this reduces deployment risk.

Final analysis: pragmatic productivity gains, but governance first​

Embedding Copilot into OneDrive and the Windows file manager is a pragmatic evolution: it puts generative AI into the places Windows users actually work. For many knowledge workers and small teams, the ability to summarize documents, ask targeted questions, generate FAQs, and compare up to five files without opening Office apps will compound into meaningful time savings. The native File Explorer and Activity Center surfaces make these micro-interactions low friction and natural to everyday workflows. (techcommunity.microsoft.com, theverge.com)
At the same time, governance is not optional. Cloud processing, file-type limitations, family‑plan nuances, and the imperfect nature of model outputs require conservative adoption for regulated content and a measured rollout strategy for enterprises. The sensible path is to pilot with clear logging and DLP controls, train users on what Copilot can and cannot do, and treat its outputs as assistive rather than authoritative.
Microsoft’s move signals a broader industry trend: AI is migrating from standalone web tools into operating system workflows. For Windows users who already live in OneDrive and Microsoft 365, Copilot’s file actions are a meaningful productivity upgrade — provided organizations pair the benefits with the right controls and expectations.
Conclusion
Copilot’s arrival inside OneDrive and File Explorer marks a visible step toward AI-assisted file management on Windows. The features — summaries, Q&A, FAQ generation, and up-to-five-file comparisons — are thoughtfully aligned to common productivity pain points and are already backed by Microsoft’s documentation and staged rollouts. But they are not a drop-in replacement for professional review or a blanket solution for multimedia workflows. The immediate opportunity is clear: faster triage and smarter file handling. The immediate responsibility is equally clear: deploy with governance, log usage, and verify compliance details before entrusting Copilot with sensitive or regulated content. (support.microsoft.com)
Source: PCWorld OneDrive gets Copilot AI features like file comparisons and summaries
 

Microsoft has quietly extended Copilot from the browser into the Windows desktop, letting eligible Microsoft 365 subscribers summon AI help directly from File Explorer and the OneDrive taskbar flyout to summarize documents, ask questions, auto-generate FAQs, and compare multiple files — all without opening Office or a web browser. (support.microsoft.com)

Isometric illustration of OneDrive Copilot linking cloud storage to documents and chat.Background / Overview​

Microsoft’s Copilot has been rolling through the Microsoft 365 stack for more than a year, appearing first in apps and on OneDrive’s web interface. The most recent step surfaces a subset of those OneDrive Copilot features in Windows itself: a set of right-click Copilot actions in File Explorer and matching controls in the OneDrive Activity Center on the taskbar. Those actions include Summarize, Ask a question, Create an FAQ, and Compare files (the last supports multi-select of up to five files). (theverge.com)
This change is primarily a UX and workflow refinement: rather than opening Word, Acrobat, or the OneDrive web page, you can call Copilot from the file list and receive structured outputs in a lightweight Copilot panel anchored to Explorer. The heavy processing still happens in Microsoft’s cloud — the desktop menu entries are essentially entry points to OneDrive Copilot functionality. That cloud processing model is explicit in Microsoft’s documentation and has implications for privacy, compliance, and corporate governance. (support.microsoft.com)

What’s available in File Explorer and the OneDrive Activity Center​

The four Copilot actions exposed in Windows​

  • Summarize — Produce a concise, human-readable summary of one file or a small batch (up to five files) to get the gist without opening each document. (support.microsoft.com)
  • Ask a question — A chat-style Q&A interface that extracts answers from the document(s) and supports follow-up prompts. (support.microsoft.com)
  • Create an FAQ — Automatically generates a list of Frequently Asked Questions and answers derived from the file’s content; useful for knowledge-base drafting and onboarding materials.
  • Compare files — When you select two to five files, Copilot generates a comparison table highlighting metadata (author, last modified, dates) and content differences or summaries — ideal for version reconciliation, contract checks, and first-pass resume screening. (support.microsoft.com)
You invoke these features by right-clicking a supported OneDrive file in File Explorer, hovering over the OneDrive submenu (Windows 11), and choosing a Copilot action; or by opening the OneDrive Activity Center from the taskbar and using the three-dot menu next to a file. The same capabilities remain available on OneDrive.com through the Copilot button. (support.microsoft.com)

Supported file types and limits (what works today)​

At launch, Copilot file actions focus on text-first formats. Supported formats include:
  • Office documents: DOC, DOCX, PPT, PPTX, XLSX
  • New Microsoft 365 structures: FLUID, LOOP
  • Universal text formats: PDF, TXT, RTF
  • Web files: ASPX, HTM, HTML
  • OpenDocument formats: ODT, ODP
Notably, images, videos, OneNote notebooks, and folder-level Q&A are not supported yet — Microsoft has flagged media and some complex file types as coming in future updates. Multi-file actions (Summarize, Compare, Ask across files) are limited to a maximum of five files at launch. There’s also a practical size guideline: many Copilot file actions are restricted to files under roughly 150 MB for now. (support.microsoft.com)

How to try it (step-by-step)​

  • Ensure you have an eligible Microsoft 365 account. For consumer users, Microsoft lists Microsoft 365 Personal and Microsoft 365 Family (with entitlement caveats for Family owners). Business tenants may require Copilot or Copilot-enabled licensing. (support.microsoft.com)
  • Make sure the files you want to use are stored in OneDrive and that you are signed into Windows with the same account. These Copilot actions operate only on OneDrive-managed files.
  • Open File Explorer (Windows 10 or Windows 11). Right-click a supported file. In Windows 10 the Copilot commands appear directly in the right-click menu; in Windows 11 you may need to hover over the OneDrive submenu to reveal Copilot actions.
  • Choose Summarize, Ask a question, or Create an FAQ for single files. For comparisons, select two to five files, right-click, and select Compare files. The Copilot pane opens and returns the output; follow-up questions work in the chat pane. (support.microsoft.com)
Tip: Be specific in prompts. Generic requests return generic results; precise instructions (e.g., “List three contractual clauses affecting payment terms and quote the nearest sentence”) yield more actionable output.

Why this matters: practical benefits​

Embedding Copilot in File Explorer reduces context switching and accelerates common file tasks. For everyday Windows users and small teams this yields real time savings:
  • Faster triage: Get an executive summary of a long report or a slide deck without launching Office or Acrobat. (support.microsoft.com)
  • Contract and version reconnaissance: Compare multiple contract drafts or quotes quickly to spot differences in dates, parties, and key clauses. (support.microsoft.com)
  • Hiring and procurement: Batch-review up to five resumes or vendor quotes and extract highlights for a first-pass filter.
  • Content creation lift: Auto-generate FAQs or extract key points from manuals and specs to accelerate knowledge base drafting.
These are assistive features: Copilot produces starting points and summaries that speed human review rather than replace it. Microsoft and other observers emphasize that outputs are not authoritative legal, financial, or medical analysis and should be validated in high-stakes contexts.

Strengths: what Microsoft did right​

  • Flow-first integration. Putting Copilot actions in the right-click menu and taskbar OneDrive flyout is a subtle, powerful UX win: it reduces friction and aligns AI assistance with where users already work. (windowsforum.com)
  • Focused scope for reliability. By starting with text-first formats and a five-file cap, Microsoft narrows the engineering surface and boosts chances of predictable, useful results. The 150 MB practical limit keeps processing manageable for web-based models. (support.microsoft.com)
  • Multi-surface parity. The functionality mirrors OneDrive web features (Summarize, Q&A, Compare), giving users a consistent experience whether they start from the browser or the desktop.
  • Immediate productivity wins. For teams that routinely triage documents, the feature reduces time spent opening and closing files — a small interaction cost that compounds into real savings.

Risks, caveats, and governance considerations​

Embedding cloud AI directly into file management introduces new considerations IT teams and privacy-conscious users must weigh.

Data residency and cloud processing​

Copilot file actions invoked from File Explorer are processed in Microsoft’s cloud services, not locally. That means file contents are transmitted to Microsoft’s servers for analysis, which raises questions for organizations with strict data residency, sovereignty, or contractual obligations. Administrators should verify processing locations and Purview protections for Copilot before broad enablement. (support.microsoft.com)

Licensing and entitlement nuance​

Consumer Microsoft 365 Family licensing has an owner-versus-member nuance: the billing owner may have different Copilot entitlements than other family members, so organizations and households should confirm who can use Copilot. Commercial tenants may require specific Copilot or Microsoft 365 Copilot licenses. Rollout timing can vary by tenant and region.

Sensitive content and auditing​

Even though Copilot respects OneDrive and SharePoint permissions (users can only act on files they already can access), the act of running Copilot should be treated like any other data operation in the audit trail. Logs of who ran Copilot, when, and on which files become important for eDiscovery and incident response. Organizations should consider including Copilot interactions in their logging and compliance workflows.

Model hallucination and overconfidence​

Copilot’s summarization and comparison outputs are powerful but not infallible. Summaries may omit nuance; comparisons may highlight differences but not replace legal redlines or line-by-line review. For high-stakes content (contracts, clinical notes, tax filings), human-in-the-loop validation remains essential.

Unsupported media and scale constraints​

If your workflows rely on images, recorded meetings, videos, or very large files, the current feature set won’t help yet. Microsoft has signaled plans to expand support for media and larger files, but teams should not depend on those capabilities until availability is confirmed. The present size guideline (~150 MB) and the five-file cap are practical bounding factors for bulk analysis. (support.microsoft.com)

Technical verification: what I checked and where​

Key technical claims and limits in this article were verified against Microsoft’s OneDrive Copilot support documentation and independent reporting:
  • The list of supported file formats and the current media exclusions are documented by Microsoft. (support.microsoft.com)
  • The five-file maximum for multi-file actions (Summarize, Compare, Ask across files) is explicitly stated by Microsoft. (support.microsoft.com)
  • The practical file size guidance (items under roughly 150 MB) and the cloud-processing model (desktop UI surfaces, cloud compute) are stated in Microsoft’s guidance.
  • Independent coverage of the File Explorer integration and right-click UX appears in outlets tracking Windows features and privacy implications. (theverge.com) (windowscentral.com)
If any of these technical details matter to compliance, privacy, procurement, or contract negotiation, validate the specifics against Microsoft’s live support pages or your Microsoft account team before enabling at scale. The cloud, rollout windows, and licensing language can change as Microsoft broadens availability.

Recommendations for IT admins and power users​

  • Review licensing and entitlements. Confirm which users (owner vs. members in Family plan, commercial Copilot license holders) can run Copilot file actions.
  • Pilot with non-sensitive data. Start with public or low-risk document sets (templates, vendor quotes) to measure accuracy and workflow gains. Track how often outputs require human edits.
  • Update logging and eDiscovery playbooks. Treat Copilot invocations as audit-worthy events and ensure logs capture who invoked the action, which files were processed, and timestamps.
  • Draft acceptable-use guidance. Tell users what to avoid (e.g., running Copilot on classified, PHI, or otherwise regulated content) until you can validate processing residency and protection levels. (support.microsoft.com)
  • Train users on prompt design. Teach how to ask specific questions and add context so Copilot returns the most useful summaries and comparisons.

A few hands-on examples and prompts that work well​

  • Executive triage: “Summarize this 60‑page report in three bullet points focusing on recommended actions and deadlines.” (support.microsoft.com)
  • Contract triage: Select three drafts and run “Compare files” then ask: “Which clauses change payment terms and what are the different notice periods?” (support.microsoft.com)
  • Resume screening: Select up to five CVs and ask: “List each candidate’s most relevant experience for a senior project manager role, including years of experience and certifications.”
  • Knowledge base creation: On a long manual, select Create an FAQ and refine: “Create five FAQs for a new user installing this product, include short step-by-step answers.”

What to expect next​

Microsoft has framed this as the initial desktop surface of OneDrive Copilot, with explicit signals that format support and limits will expand. Expect iterative updates that:
  • Broaden supported file formats to include images, meeting recordings, and OneNote. (support.microsoft.com)
  • Raise the multi-file cap beyond five and increase the supported file-size ceiling.
  • Extend similar Copilot actions into SharePoint document libraries and possibly enhance offline or device-local capabilities for Copilot Plus PCs with NPUs (where some AI workloads can run locally). These are roadmap-like items Microsoft has signaled or that have appeared in related insider testing. (theverge.com)
Because rollouts are staged by tenant, region, and client version, availability will continue to be gradual — confirm your environment’s update cadence and OneDrive client version if you’re waiting for the feature.

Final assessment​

Putting Copilot actions into File Explorer is a practical, well-scoped productivity improvement that aligns with how people actually manage files on Windows. For text-heavy tasks — contract triage, quick report summaries, multi-document Q&A — Copilot in File Explorer delivers tangible time savings and reduces the need to switch to a browser or open multiple apps.
However, the integration is not a drop-in replacement for careful human review, and it introduces governance questions that organizations must treat seriously: cloud processing, auditability, and licensing boundaries are the most important of these. Until image, audio, and very large-file scenarios are supported and processing guarantees are more explicit, Copilot File Explorer actions should be treated as a productivity assistant rather than an authoritative source.
For everyday Windows users and small teams already working in OneDrive, the feature is worth trying now — but IT teams should pilot deliberately, update policies, and verify compliance controls before wider enablement. (support.microsoft.com)
Microsoft’s move is a clear example of incremental AI integration that favors convenience and discoverability. It reduces friction for busy users and points the way toward a future where operating systems surface intelligent, context-aware helpers at the point of action — provided organizations and individuals treat the outputs with appropriate caution and verification. (theverge.com) (support.microsoft.com)
Source: ZDNET Copilot's new File Explorer tricks are serious OneDrive time-savers - how to try them
 

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