Troubleshooting Sigsync signature add-in for Outlook Issues
Microsoft’s security architecture and policy enforcement can sometimes result in errors during the automatic deployment of Sigsync signature add-in for Outlook. These issues typically stem from permission restrictions, connectivity challenges, tenant-level configurations, service health incidents, or directory attribute limitations.
The following section outlines common configuration errors along with recommended solutions:
Problem:
You may receive an ‘Unauthorized Access’ error caused by security measures such as Conditional Access policies or Multi-Factor Authentication (MFA).
Resolutions:
- Verify Sign-in Credentials
- Ensure that you sign in using Global Administrator credentials with the necessary account permissions before proceeding.
- Contact Support
If you need further assistance with the Add-in deployment, please contact Sigsync Support.
Problem:
During the connector setup process, you may encounter the following error:
‘Connecting to remote server ps.outlook.com failed with the following error message. For more information, see the about_Remote_Troubleshooting Help topic.’
This typically occurs when PowerShell fails to establish a remote session with Exchange Online due to local system, network, or policy-related issues.
For a more detailed explanation and solutions, refer to:
Problem:
When deploying the add-in anew, the process fails because the existing add-in cannot be removed automatically.
Example error message:
Failed to check or remove add-in: The app "Sigsync Signatures Add-in for Outlook" is managed by organization administrators and can't be uninstalled by end users.
Cause:
If the previous add-in was installed manually via Microsoft 365 Integrated Apps, automated removal during deployment is not supported.
Resolution:
To proceed, please log into your Microsoft 365 tenant and manually uninstall the existing add-in. Once removed, you can retry deploying the add-in. Manual deployments must be handled manually for removal, as the deployment system cannot remove them automatically.
Problem:
Authentication fails while signing in during connector setup.
Resolution:
Ensure that you are signing in with a valid Global Admin account that has not been blocked or restricted for sign-in.
Problem:
The add-in deployment fails due to API or server communication issues.
Resolution:
- Wait for a few minutes and retry.
- Ensure firewall or network settings don’t block access to Microsoft 365 APIs.
- Check for any Microsoft service outage under Admin Center > Health > Service Health.
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