WiseStamp for IT › Microsoft 365 › Step 9 of 12 — Go-Live Checklist
What WiseStamp requires, and what we recommend beyond it: the product requirement to mark an integration live is a single test email from any active employee with an assigned signature — the integration status updates automatically after that first email. The pilot-and-rollout process below goes further on purpose; treat it as recommended IT acceptance practice rather than a product requirement.
Pre-go-live: configuration sign-off
Confirm the setup is complete before testing with real users.
☐ Entra ID directory connected; expected employees imported (Connect Microsoft Entra ID).
☐ Synced fields (title, department, phone) verified against Entra ID.
☐ Deployment method configured:
☐ Outlook Add-In deployed centrally (Deploy the Outlook Add-In), and/or
☐ Server-side connectors + transport rules created and enabled (Server-Side Deployment).
☐ (Hybrid) Both methods configured; duplicate-prevention confirmed in design.
☐ (Platform/Enterprise) SSO configured and tested, if in scope (SSO with Entra ID (SAML)).
☐ (Enterprise) Security Group sync enabled and reflecting membership, if in scope (Sync Microsoft Security Groups).
☐ Signatures assigned (Primary Signature set; groups assigned where used).
☐ (Server-side) SPF verified; DKIM aligned; RTF set to Never.
Stage 1 — Pilot group
Select a small pilot (5–10 users) spanning the environments you support: Outlook desktop (Windows), Outlook for Mac, Outlook web, Outlook mobile (iOS/Android), and — for server-side — at least one non-Outlook sender (mobile mail app or CRM).
For each pilot user:
☐ User set to Active in WiseStamp.
☐ (Add-In) User restarted Outlook desktop and refreshed Outlook web so the Add-In loads.
☐ New email shows the correct signature.
☐ Reply shows the expected signature behavior.
☐ Forward shows the expected signature behavior.
☐ Signature renders correctly to an internal recipient.
☐ Signature renders correctly to an external recipient.
☐ Images/logos load and are correctly sized (not enlarged/broken).
☐ No duplicate signature appears (if it does, check for manual copy/paste signatures — Troubleshooting Reference).
☐ (Server-side) Signature appears when sending from a non-Outlook device.
☐ (Dark mode) Signature is legible in dark mode clients.
Validation matrix (record results)
User | Client/Device | New | Reply | Forward | Internal | External | Duplicates? | Notes |
Outlook desktop (Win) | ||||||||
Outlook for Mac | ||||||||
Outlook web | ||||||||
Outlook mobile | ||||||||
Non-Outlook (server-side) |
Stage 2 — Targeting and rules check (if used)
☐ (Server-side rules) Each rule applies to the intended senders, email types, and recipient conditions.
☐ Rule priority order produces the intended result when multiple rules match.
☐ Group-based signature assignment maps the right signature to the right group.
Stage 3 — Full rollout
☐ Confirm enough seats are available for all employees you intend to activate (Ongoing Admin Guide).
☐ Set New employee default status to Active if you want automatic activation (Ongoing Admin Guide).
☐ Activate remaining employees (bulk: select > Set status > Active).
☐ (Add-In) Communicate the restart/refresh requirement to employees (Employee Rollout Handoff).
☐ Send the employee handoff communication (Employee Rollout Handoff).
Stage 4 — Post-go-live monitoring (first 1–2 weeks)
☐ Watch for "no signature" or "duplicate signature" tickets; triage with Troubleshooting Reference.
☐ (Server-side) Confirm outbound mail flow is healthy; no delivery delays attributable to routing.
☐ Confirm new hires added in Entra ID appear in WiseStamp on the next daily sync.
☐ Confirm leavers removed in Entra ID are removed/deactivated on the next sync.
☐ Ensure several admins retain Exchange admin center access for rapid response.
Rollback / safety
Server-side: if mail stops flowing, disable the Identify messages to send to WS SMTP rule to bypass routing, then contact support (Server-Side Deployment, Troubleshooting Reference).
Add-In: if needed, disconnect/remove the Add-In from the Microsoft 365 admin center (Deploy the Outlook Add-In).