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I have tried the new config with special let's encrypt allowance.
It works fine, I had added the following lines (see below) to do the same I think but could now remove it from my config.
I have tested it and it allows the challenge without the directory configuration.
Does it make sense?

#Directory{
#DirectoryID = challenge
#Path = /.well-known/acme-challenge
#AccessList = allow 66.133.109.36,deny all
#AlterList = deny all
#}

Yes, Hiawatha v10.2 always allows access to /.well-known/acme-challenge/ and will ignore any AccessList or PasswordFile setting.

ok that's a great idea and that works fine. For windows, I have made an unattended batch in powershell to renew the certificate for those interested.