When you try to make a digital sign in Windows 10 and you use a digital certificate stored in Windows´certificate managerit will silently fail if the private key is marked as non-exportable. If you reinstall the certificate and make the private key exportable then it will work. This is the case in the various programs of the suite and all the instances where a digital sign is involved (sign an existing PDF, sign an odt/ods etc, export to PDF and sign.
Context: https://t.me/libreoffice_es/64181
Rodrigo's message on Telegram: "Como dije, creo que Libreoffice en vez de usar adecuadamente las APIs criptográficas de Windows copia directamente la clave privada, y si no es exportable falla silenciosamente.. Es un bug claro." Translated to: "As I said, I think that LibreOffice, instead of properly using the Windows cryptographic APIs, directly copies the private key, and if it is not exportable, it fails silently. It is a clear bug." Thank you for the report, Rodrigo. Would you mind checking if this is still relevant in a currently-maintained version of LO, preferably 24.2?