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Because the network does NAT64/DNS64, this must mean that AutoUpdate does some funky IPv4 address embedding. I will do some tcpdump debugging later.After connecting it temporarely to weird IPv4-only stuff. After connecting it temporarily to the dual stack network, I did get the updates inmediately.the updates immediately.

I created a couple of tcpdumps, and it looks like the AutoUpdate tool has some hardcoded logic that makes it only use A records for download.microsoft.com, which of course fail:

Image Added

Interestingly, had the tool queried for a quad-A record, it would have worked:

administrators-macbook-pro:~ root# host -t aaaa download.microsoft.com
download.microsoft.com is an alias for download.microsoft.com.nsatc.net.
download.microsoft.com.nsatc.net is an alias for main.dl.ms.akadns.net.
main.dl.ms.akadns.net is an alias for intl.dl.ms.akadns.net.
intl.dl.ms.akadns.net is an alias for dl.ms.georedirector.akadns.net.
dl.ms.georedirector.akadns.net is an alias for a767.ms.akamai.net.
a767.ms.akamai.net has IPv6 address 2001:610:148:ffff:b0b0::58dd:d830
a767.ms.akamai.net has IPv6 address 2001:610:148:ffff:b0b0::58dd:d83a

Boo!!!

Ubuntu servers not ready

Trying to debug OpenDNSSEC packages on one of my IPv6-only systems but unfortunately some bumps in the way. The system keyserver.ubuntu.com does not have IPv6 connectivity, so adding GPG keys using apt-key does not work:

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