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We have a virtual machine which uses two custom repositories, first is Mono Xamarin, I followed the official guide on installation and it works.

However we have custom repository created with Aptly which is signed with GPG as well. When I add this repository to the list and add our public key (via apt-key add my_key.asc), the apt-get update says

Failed to fetch https://our-repo/debian/dists/jessie/main/binary-amd64/Packages  
gnutls_handshake() failed: Public key signature verification has failed.

I am really not sure why because it works on all other machines. I am 100% sure that the key is correct and there is no difference to other machines except adding Xamarin repo as well. Additionally we handle this with Puppet so there really should be no difference compared to other VMs.

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    That looks like a TLS problem (your SSL certificate, or the valid algorithms on both sides), not a GPG problem. – Stephen Kitt Oct 18 '16 at 8:58
  • Is it possible, that https://our-repo/ is using a self-signed certificate? – lw1.at Oct 18 '16 at 9:03
  • Yes, it is. So that's why we are installing apt-transport-https package as well. And also we are adding this line into /etc/apt/apt.conf - Acquire::https::our-repo/debian::Verify-Peer "false"; – Petr Mensik Oct 18 '16 at 9:09
  • However thanks for pointing to the right direction, I am digging into it right now and it seems broken for some reason – Petr Mensik Oct 18 '16 at 9:09

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