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:
The deployment of the new add-in fails because an existing version of the add-in is already installed and cannot be removed automatically.
Example error messages:
- 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.
- Deployment failed: Your administrator has already installed this add-in via centralized deployment. Contact your administrator to remove the add-in before you install it from here.
Cause:
If the add-in was previously deployed manually through Microsoft 365 Integrated Apps, the automated deployment system cannot uninstall it.
Also note that Office 365 Global Admin and Exchange Admin roles are required for proper deployment of the Add-in.
Resolution:
Sign in to your Microsoft 365 tenant and manually remove the existing add-in from Integrated Apps. After removal, retry deploying the add-in.
Manually deployed add-ins must be manually uninstalled—they are not managed by centralized deployment.
Click here to view the steps for removing the add-in from Integrated Apps.
Grant Admin Roles
If the add-in deployment fails, ensure the admin has Office 365 Global Admin and Exchange Admin roles. If not, create a new admin with these roles and try again.
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:
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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