WiseStamp for IT › Microsoft 365 › Step 12 of 12 — Troubleshooting Reference
Quick index
Symptom | Section |
Signature not appearing in Outlook | section 1 |
Two / duplicate signatures | section 2 |
Outbound mail not sending (server-side) | section 3 |
Signature missing only on some devices | section 4 |
Employees missing after sync | section 5 |
Admin can’t log in | section 6 |
Images broken / oversized | section 7 |
"Signature too long" error | section 8 |
section 1 — Signature not appearing in Outlook
Work through in order:
Directory connected but no deployment yet. Connecting Entra ID does not place signatures. Confirm the Outlook Add-In is connected (Deploy the Outlook Add-In) or server-side is configured (Server-Side Deployment).
Employee not Active. The Add-In only signs Active employees with a Primary Signature assigned. Check the Employees page (Deploy the Outlook Add-In, Ongoing Admin Guide).
Client not refreshed. Have the user restart Outlook desktop and refresh Outlook web so the Add-In loads.
Add-In not propagated. After centralized deployment, Microsoft can take time to push the Add-In to all mailboxes. Confirm it shows in the Microsoft 365 admin center (Integrated apps).
Default signature not selected (manual/native check).
Outlook desktop: File > Options > Mail > Signatures; confirm a signature is set for New messages and Replies/forwards.
Outlook web: Settings (gear) > View all Outlook settings > Mail > Compose and reply; enable signature for new messages and replies/forwards; Save.
Email format not HTML. File > Options > Mail > Compose messages in this format = HTML.
Advanced (desktop): Update Outlook (File > Office Account > Update Options > Update Now); run in safe mode (outlook /safe); repair Office (Control Panel > Programs and Features > Office > Change > Repair); reset nav pane (outlook.exe /resetnavpane).
section 2 — Two / duplicate signatures
Most common cause: the user has a manually pasted (copy/paste) signature in Outlook in addition to WiseStamp. Remove the manual signature in Outlook signature settings, restart Outlook.
Hybrid mode is designed to prevent duplicates (server-side only appends when no WiseStamp signature is detected). If duplicates persist in hybrid, confirm the client-side signature is being detected correctly and check for a stray manual signature.
section 3 — Outbound mail not sending (server-side)
This should not happen in normal operation. If it does:
Emergency bypass: Exchange admin center > Mail flow > Rules > open Identify messages to send to WS SMTP > toggle off. Mail then delivers without a server-side signature.
Contact WiseStamp support / your CSM for investigation.
Reconnect when resolved: In WiseStamp, Integrations > Disconnect, then Connect for Microsoft Exchange and follow the prompts to re-establish the connection.
Keep multiple admins with Exchange admin center access so bypass can be applied quickly.
If the automated connection shows errors, disconnecting and reconnecting the server-side solution from Integrations often clears transient connection issues.
section 4 — Signature missing only on some devices
Add-In only covers Outlook clients where it’s installed and signed in. Mobile mail apps that aren’t Outlook, or non-Outlook senders, won’t get a client-side signature. For universal coverage use server-side or hybrid (Setup Overview, Server-Side Deployment).
Confirm the device’s Outlook build meets the minimum versions (Prerequisites Checklist).
section 5 — Employees missing after sync
Confirm the directory integration is healthy and daily sync is enabled (Settings > Sync & Automations).
If using selective sync, the missing users' department/OU may be excluded — review the Sync specific selection.
If using Security Group sync, confirm the users are explicit, direct members of the group (no nested groups) and that the correct Group ID is in use (Sync Microsoft Security Groups).
Remember: auto-synced accounts remove users who no longer exist in the directory; a "missing" user may have been removed from Entra ID.
A manual resync can be triggered from Sync settings.
section 6 — Admin can’t log in
Check for outages, then refresh the browser and clear cache/cookies; retry.
Chrome extension login loops: go to chrome://extensions/, remove the WiseStamp extension, then log out and back in.
Subscription lapse: verify the subscription is active; renew if needed, which restores login and signature display.
Wrong audience: only owners/admins log into the main account. Employees do not log in — they use the Employee Hub.
SSO issues: confirm the user is assigned to the WiseStamp app in your IdP and that SAML endpoints/RelayState match (SSO with Entra ID (SAML)).
section 7 — Images broken / oversized
Follow WiseStamp’s image size/quality best practices; oversized source images can render enlarged. (See the image best-practices material in the knowledge base.)
Confirm images are hosted/embedded as intended and that the client isn’t blocking remote images.
Check dark-mode rendering separately — optimize the signature for dark mode if logos disappear on dark backgrounds.
section 8 — "Signature too long" error
This is a known Outlook limitation handled in WiseStamp’s "Signature too long" guidance. Reduce signature size (trim embedded image weight, simplify markup) per that guidance.
When to escalate to WiseStamp support
Server-side mail flow failures after applying the emergency bypass.
Manual server-side configuration (must be enabled by support; routing code issued by support).
Security Group sync enablement (Group ID entered by WiseStamp).
SSO domain creation and metadata finalization.
Any IP-allowlist requirement for server-side routing — confirm the current ranges with WiseStamp support.