Expired licence on Adobe Acrobat Pro 8

A user has been getting an expired license message when trying to digitally add his signature to PDF documents. We've seen it before and have imported his key file, but this time it has an expiration date that is actually past. I have tried to run the licence clean up tool, and still have the same results. Any suggestions?

Hi CambridgeAdobe,
You might refer the KB doc links mentioned below to troubleshoot licensing issues:
For Windows: Error "Licensing has stopped working" | Windows
For MAC: https://helpx.adobe.com/x-productkb/global/error-licensing-stopped-mac-os.html
Let me know if this helps.
Regards,
Anubha

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