Deploying Cowork at Scale: Packaging, MDM, and Policy Integration for Enterprises

Hook: Why enterprise IT teams should treat Cowork deployment like a security project — not a UX demo

If you're responsible for corporate desktops, you already feel the tension: developer‑grade desktop AI (Anthropic's Cowork) can multiply productivity for engineers and knowledge workers, but it also introduces new vectors for data access, telemetry, and compliance risk. In 2026, with desktop agents getting filesystem privileges and autonomous capabilities, a laissez‑faire rollout can quickly become a costly incident. This guide gives you a pragmatic, step‑by‑step path to packaging, integrate with MDM and SSO, enforce group policies, and instrument telemetry so you scale Cowork across fleets while minimizing risk.

Quick summary — what to do first (inverted pyramid)

• Plan: map data flows, regulatory boundaries, and use cases.
• Proof of concept: run a closed pilot (50–200 devices) with strict telemetry and rollback hooks.
• Package per OS: produce signed MSI/MSIX for Windows, notarized PKG/DMG for macOS, and DEB/RPM or Snap for Linux.
• Integrate identity: configure SSO (OIDC/SAML) and SCIM provisioning; enforce device posture via conditional access.
• Apply MDM policies: per‑app network restrictions, file ACL rules, remote uninstall & kill switch.
• Instrument telemetry: auth metrics, API usage, unexpected file access, install health — ship to SIEM.
• Roll out in phases with explicit go/no‑go criteria and an incident playbook.

Why now — 2026 context and trends

By late 2025 and into 2026, enterprise interest in desktop AI exploded. Anthropic's Cowork (Jan 2026 research preview) brought Claude Code powers to GUI users, enabling autonomous file manipulation and complex task automation. Simultaneously, federal and enterprise buyers increased demand for FedRAMP and private tenancy AI platforms — a trend highlighted by acquisitions and certifications during 2025. Regulators and standards bodies (notably the ongoing NIST AI Risk Management Framework evolution and the EU AI Act implementation) have pushed security and data‑use controls to the top of procurement checklists.

What this means for IT leaders

• Desktop agents now require the same governance as SaaS and internal agent software.
• Identity and device posture are first‑class controls for safe access.
• Packaging, telemetry, and group policy become operational pillars, not optional extras.

Risk model: what you must defend against

Before packaging and deployment, define the risks you need to mitigate. Typical risk vectors for Cowork include:

• Data exfiltration — agent reading local files or network shares and sending content to external APIs.
• Unauthorized access — compromised accounts or devices using Cowork to access corporate data.
• Telemetry leakage — application logs containing PII or sensitive artifacts.
• Supply chain & update risk — unsigned builds or man‑in‑the‑middle updates.
• Policy drift — inconsistent configuration across device groups.

Blueprint: secure architecture for enterprise Cowork

At a high level, your architecture should combine: identity enforcement (SSO + conditional access), endpoint control (MDM + EDR), network controls (per‑app proxy/VPN, egress allowlist), and observability (telemetry to SIEM). A reference stack:

• Identity: Azure AD / Okta / Ping with OIDC or SAML and SCIM for provisioning.
• MDM: Microsoft Intune, Jamf, Workspace ONE for packaging, distribution and configuration.
• EDR: CrowdStrike, Microsoft Defender, or SentinelOne for process control and response.
• Network: per‑app proxy or per‑app VPN, inline DLP, and firewall egress allow‑lists.
• Observability: Splunk/Elastic/Datadog/SIEM for telemetry ingestion, plus SOC runbooks.

Packaging: practical steps per OS

Windows (enterprise recommended path)

Deliver Cowork as a signed MSIX or Win32 app managed by Intune. MSIX is preferred for predictable lifecycle and cleaner uninstall, but many vendors still ship MSI. Key steps:

1. Obtain the vendor MSI/MSIX and verify signature. If only an EXE is provided, create a wrapper MSI using WiX or Advanced Installer.
2. Sign packages with your code‑signing certificate (best practice: use hardware security module).
3. Use Intune Win32 app packaging (IntuneWin) if you need pre/post scripts. Example: IntuneWinAppUtil.exe to bundle installer, detection rules using file existence or registry keys, and silent install command (msiexec /i vendor.msi /qn).
4. Configure assignment to device groups (Pilot → Broad Pilot → All). Make the app available as "Required" for pilot groups with scope tags for admins.
5. Define update behavior: disable auto‑update if you want centralized control; use Intune to push new versions on a scheduled ring.

macOS

Apple's notarization and signing policies matter in 2026. Use Jamf or Intune for macOS management:

1. Produce a signed PKG/DMG and notarize via Apple notarization services. Prefer a PKG for Jamf management.
2. Create a Jamf policy or Intune macOSLob app. Include preinstall scripts to set configuration profiles and postinstall scripts to verify preferences.
3. Distribute configuration profiles to enforce privacy settings, restrict file access, and inject managed preferences (plist keys) that toggle agent capabilities.

Linux

Linux fleets vary. For enterprise Debian/Ubuntu and RHEL/CentOS families:

• Provide DEB/RPM packages and ensure packages are signed. Use your apt/yum repo or internal artifact repo (Artifactory, Nexus).
• Use configuration management (Ansible, Puppet) or an MDM for Linux (Canonical MAAS/ Landscape) to control installation, updates, and configuration.
• Ship a systemd unit for the agent and manage service restarts through automation.

Identity and SSO: lock the door first

Your identity layer is the fastest way to reduce risk. Configure:

• SSO (OIDC/SAML) integration so authentication flows through corporate IdP. Avoid local accounts where possible.
• SCIM for automated provisioning and deprovisioning of user accounts and group memberships.
• Conditional Access policies that require device compliance signals from MDM (e.g., Intune device compliance) before allowing Cowork to exchange tokens.
• Short‑lived tokens and ability to centrally revoke sessions. Test application logout and token revocation paths during pilot.

Recommended SSO policy examples

• Require MFA for first‑time Cowork login and after device posture changes.
• Block access from unmanaged devices; allow managed devices with compliant posture.
• Force re‑authentication on suspected lateral movement or anomalous resource access.

MDM & group policies: enforce and protect

Use MDM to enforce settings that reduce the agent's blast radius. Examples:

• Per‑app network controls: route Cowork through a corporate proxy or per‑app VPN.
• File system ACLs and sandboxing: limit paths the agent can read/write via OS controls or app sandboxing where possible.
• Group Policy Objects (Windows): set registry keys to disable features (e.g., CLI execution, plugin installation, local storage) and to configure telemetry endpoints.
• Configuration profiles (macOS): managed preferences (plist) that lock down capabilities like file access, camera, or screen recording.
• Remote kill switch: an MDM policy that can uninstall or quarantine the app immediately.

Example Windows group policy items to consider

• Registry key to disable local file system write operations for the app (vendor provided).
• Configure proxy and certificate trust configurations so the app's TLS traffic is inspected.
• Define an app‑allow list in Windows Defender Application Control to prevent rogue agents.

Telemetry: what to collect and how to act

Design telemetry for detection and compliance while minimizing PII capture. Instrumentation should include:

• Authentication metrics: successful/failed logins, MFA events, token issuance rate.
• Install and update health: install success rate, crash rate, version drift across fleet.
• API usage: API calls per user, unusual volumes, destinations (external vs private endpoints).
• Data access events: large file reads, access to sensitive directories, unexpected exports.
• EDR signals: process forks, suspicious child processes, or attempts to spawn shells.

Ship events to your SIEM with structured fields: timestamp, device_id, user_id (pseudonymized if needed), event_type, summary, indicator. Set retention and redaction rules (e.g., redact file contents unless explicitly required for an incident). Define alert thresholds (e.g., >10 large file read events in 1 hour) and automate initial containment (revoke token + quarantine device).

Compliance & privacy controls

Map the product's capabilities to your compliance controls. Typical items:

• Data residency: ensure AI inference endpoints meet regional requirements or use private tenancy.
• PII handling: intercept and block PII in outbound requests using DLP or inline proxy policies.
• Auditability: retain event trails for required windows per regulation. Consider Docs‑as‑Code approaches for long‑term, auditable configuration and runbooks.
• Third‑party assessment: insist on SOC 2/FedRAMP/ISO27001 artifacts for procurement.

Phased rollout playbook (detailed)

Pilot — 2–4 weeks

1. Pick a small, security‑savvy group (50–200 users). Configure strict telemetry and one rollback path.
2. Deploy via MDM with managed preferences and per‑app network routing to an inspection proxy.
3. Collect metrics: auth failures, unusual file access, API volumes.
4. Run tabletop incident scenarios (token compromise, data exfil) and validate response steps.

Extended pilot — 6–8 weeks

1. Expand to 500–2000 users across teams (dev, docs, legal) to validate policy coverage.
2. Refine group policies, MDM profiles, and update procedures.
3. Assess latency and costs (API calls, egress) and adjust quotas or caching strategy.

Production roll — phased by org unit

1. Use ringed deployments (Rings 1–4). Move to next ring only after hitting operational KPIs (install success >98%, auth failures <1%, no critical incidents).
2. Monitor cost and telemetry continuously, and keep an open rollback window (via MDM kill switch).

Incident playbook & rollback actions

Be prepared. A concise playbook:

1. Contain: revoke application access at IdP (invalidate tokens via SSO), push MDM quarantine or uninstall, and isolate device in network.
2. Investigate: pull telemetry from SIEM, check EDR traces, capture relevant artifacts (preserving chain of custody).
3. Remediate: rotate credentials, apply updated policies, push hotfix package, and forward indicators to vendor.
4. Communicate: follow internal privacy notification and legal escalation paths.

Example case study: Acme Tech (hypothetical)

Acme Tech (2,500 endpoints) needed to roll out Cowork for R&D while preventing IP leakage. They used this approach:

1. Pilot 100 engineers with Jamf + Okta. Per‑app VPN routed Cowork traffic through an inline DLP proxy.
2. Telemetry surfaced a pattern: a particular plugin attempted to access archived design files. The SOC configured an alert and the policy team pushed an MDM profile to block plugin installation.
3. After three rings and two minor policy changes, Acme rolled out to all developers. They achieved 0 data‑loss incidents and reduced incident mean time to contain by 65% because revocation via Okta and MDM quarantines were scripted and tested.

Advanced strategies & future‑proofing

• Feature toggles and server‑side controls: prefer vendor features that support server side flags so you can disable capabilities without redeploying clients.
• Gateway AI approach: put an internal inference gateway in front of vendor endpoints to centrally enforce policies, rate limits and data filters.
• Supply chain controls: require signed updates and maintain your own trusted update mirror where feasible.
• Privileged environment: allow the most powerful agent features only in hardened, monitored developer workstations or bastion hosts — consider edge‑first laptops and locked‑down hardware for those seats.
• Vendor lock‑in mitigation: abstract the auth and egress layers so replacing the vendor requires minimal configuration changes.

Checklist: essential deliverables before broad deployment

• Signed packages for each OS and documented install and rollback commands.
• IdP integration (SSO + SCIM) configured and tested.
• MDM policies for per‑app network, file access, and remote uninstall.
• EDR and SIEM ingestion enabled; alert stories created and tested.
• Regulatory mapping and DLP rules validated with Legal and Privacy.
• Runbook & tabletop exercise completed and approval from Security Governance.

Start small, measure everything, and keep a kill switch at your fingertips.

Closing: the operational reality in 2026

Desktop AI like Cowork will become table stakes for developer productivity in 2026. Enterprises that treat deployment as a security and operations program — with clear packaging, identity controls, MDM enforcement, and rigorous telemetry — will get the productivity upside without the headline risks. The techniques above reflect recent market moves (vendor enterprise offerings, FedRAMP interest in AI platforms, and tighter guidance from standards bodies) and translate those trends into operational steps you can take this quarter.

Actionable takeaways

1. Don’t permit broad access on day one. Start with a hardened pilot.
2. Integrate with SSO and enforce device posture before allowing any agent tokens.
3. Ship signed packages via MDM and ensure per‑app network controls are in place.
4. Stream telemetry to SIEM/observability with privacy‑aware redaction rules and automated containment flows.
5. Keep vendor features toggleable and maintain a tested rollback path.

Call to action

Ready to build a safe rollout plan for Cowork? Download our checklist and an Intune/Jamf policy template (updated for 2026) to accelerate your pilot. If you want a tailored rollout blueprint for your environment, contact our experts for a 90‑minute workshop that maps packaging, SSO, MDM and telemetry to your compliance needs.

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