Simon 2.0: Copilot Admin Setup Guide

Southwest has 16 Microsoft 365 Copilot licenses. These include built-in semantic search capabilities that are not yet configured. This guide walks through enabling Copilot search for a pilot with Jim Mullan's Construction & Development team.

Pilot Scope

For the full project scope including success criteria, risks, and rollout plan, see the POC Scope Document.

Confirm these before starting configuration:

License Tier

Check Southwest's base M365 license tier. This determines which features are available out of the box.

M365 Admin Center › Billing › Your products

Copilot License Pool

Confirm which of the 16 Copilot licenses are currently assigned and which are available.

M365 Admin Center › Billing › Licenses › Microsoft 365 Copilot

Jim's SharePoint Access

Confirm Jim currently has read access to the three pilot folders in SharePoint. Copilot inherits SharePoint permissions, so if Jim can access these folders today, Copilot will be able to search them.

Check the Crawl Log

SharePoint Admin Center › More features › Search › Crawl Log

Filter by the site URL(s) containing Jim's folders and check for errors:

• Green = successfully crawled and indexed
• Red = errors (usually permissions or corrupted files)
• Missing = site may not be crawled yet

If everything is green, move on. If there are errors, the most common causes are permission issues with the crawl service account or unsupported file types.

Force a Recrawl (if needed)

If content seems out of date or a library isn't appearing in the crawl log:

1. Navigate to the specific document library in SharePoint
2. Open Library Settings › Advanced Settings › Reindex Document Library
3. Content will be picked up in the next crawl cycle (within ~4 hours)

File Type Support

If Jim's folders contain many legacy .doc/.xls files, Copilot may not fully index them. Converting to modern formats would improve results, but this is not a blocker for the pilot.

M365 Admin Center › Users › Active Users › Jim Mullan › Licenses and apps

1. Find Jim Mullan's user account
2. Under "Licenses," check if Microsoft 365 Copilot is assigned
3. If not, assign it from the available pool
4. Save changes

These org-level settings can silently block Copilot from working. Check them before Jim starts testing.

Where to check

M365 Admin Center › Settings › Org settings › Services › Privacy

Confirm "Connected experiences that analyze content" is enabled. If it was previously turned off for privacy reasons, it needs to be re-enabled for Copilot to function.

Copilot-Specific Settings

M365 Admin Center › Copilot › Settings

Review the settings tabs:

• User access: Confirm Copilot Chat is enabled for licensed users
• Data access: Web search can be on or off depending on preference. For the pilot, having it on gives Jim richer results.
• Copilot actions: Review any plugin restrictions if applicable

Outlook Copilot

Jim wants Copilot in Outlook for email summarization and search. This should be enabled automatically with the Copilot license, but verify under Copilot Settings that Outlook is not excluded.

Once enabled, Jim opens Outlook, clicks the Copilot icon in the ribbon, and can:

• Summarize long email threads
• Search across his inbox with natural language
• Draft replies based on thread context

For the Pilot

If Jim's existing SharePoint permissions are correct, no scoping changes are needed. This is the fastest path to getting Jim testing.

Restricting Other Sites (Optional, Future)

If there's a concern about Copilot surfacing content from other departments that Jim has access to but shouldn't see via Copilot, there are two options to apply later:

Matt Cooper at Volta Effect needs read-only access to Jim's three SharePoint areas for discovery analysis. Two options, depending on what level of access is appropriate:

Option A: App Registration

Microsoft Entra Admin Center › Entra ID › App Registrations › New Registration

1. Name: "Volta AI Lab - SharePoint Discovery"
2. Account type: "Accounts in this organizational directory only"
3. Redirect URI: Leave blank
4. Click Register. Note the Application (client) ID and Directory (tenant) ID.
5. Under Certificates & secrets, create a client secret and securely share it with Matt.

Grant Scoped Permissions

1. In the app registration, go to API Permissions › Add a permission › Microsoft Graph
2. Select Application permissions (not delegated)
3. Add: Sites.Selected
4. Click Grant admin consent

Grant Access to Specific Sites

Run these PowerShell commands to grant read-only access to each of Jim's sites:

Share the Application (client) ID, Tenant ID, and client secret with Matt securely (not via email). Once configured, Matt will confirm access is working.

Option B: Guest Account

1. Entra Admin Center › Users › Invite external user
2. Enter: matt@voltaeffect.com
3. After the invitation is accepted, add Matt as a Visitor to the 3 SharePoint sites
4. Matt can then browse and search through the SharePoint web interface

This is not needed for the pilot, but is included as reference for when the team is ready to address PII scanning alongside the SharePoint cleanup initiative.

What's Available by License

SIN Number Detection (When Ready)

Microsoft Purview › Data Loss Prevention › Policies › Create Policy

1. Choose Custom template
2. Select SharePoint sites as the location to protect
3. Add condition: Content contains › Sensitive info types › Canada Social Insurance Number
4. Set action to Report only (no blocking, just surfaces what's there)
5. Run for 2-4 weeks to understand the scope before considering enforcement

Preventing Copilot from Surfacing PII (Future)

Once DLP policies are in place, a separate policy can specifically prevent Copilot from processing documents that match PII patterns:

• Create a DLP policy scoped to "Microsoft 365 Copilot and Copilot Chat"
• Action: "Prevent Copilot from processing content"
• Result: even if a user has access to a document containing a SIN number, Copilot won't reference it in responses

After completing steps 1-4, run these tests to confirm Copilot is working for Jim.

Test 1: Copilot Chat

Have Jim open Microsoft 365 Copilot Chat (microsoft365.com/chat or the Copilot app in Teams) and try:

• Pass Copilot returns results from Jim's SharePoint folders with file references
• Fail Returns only web results or nothing. Check: license assignment, privacy settings, crawl log errors.

Test 2: Copilot in Outlook

Jim opens Outlook, selects a long email thread, and clicks the Copilot icon to summarize it.

• Pass Copilot generates a summary of the thread
• Fail Copilot icon is missing or grayed out. Check: "Connected experiences that analyze content" privacy setting.

Test 3: Permission Boundaries

Ask Copilot about content from a site Jim should not have access to (e.g., HR files). Copilot should not return results from restricted areas.

• Pass No results from restricted sites
• Fail Content from restricted sites appears. Review SharePoint permissions on those sites.

Troubleshooting

If you hit any roadblocks or have questions during setup, reach out to Matt Cooper at Volta Effect:

• Email: matt@voltaeffect.com
• Phone: 902.880.6288

Matt is available to screen-share and walk through any configuration step if needed.