Hi,
Can I ask if there is any update on the issue that I face?

Hi Werner,
I have performed some experiments on the issue I have and the following are the results:

Hi Werner,
The issue is the following:
I have 2 certificates in the trusted-certificates folder that is searched by gpgsm (C:\ProgramData\Gnu\etc\gnupg\trusted-certs) which I want to trust. When dirmngr starts, it reads the Windows trusted certifcate store (certlm.msc for both system and user - I don't know the path / location of the windows certificates folder outside certlm) and builds the list of certificates to use. Once this list is read and if any duplicates are found in the trusted-certificate folder, it ignores them - they are already present.