(cc: David Kalnischkies as this may answer his question too)

Hello Pablo,
>
> I run into the same issue when proxying my apt through apt-cacher-ng.
> Not without any proxy in between.
>
> It seems you're using a proxy, too:
>
> > Acquire::http::Proxy "http://10.137.255.254:8082/";;
>
> Out of curiosity and hopefully narrowing down the issue: What kind of
> proxy is this on your side?
>

You are right, there is a proxy and I failed to mention it. D'oh!

This report comes from a Qubes OS "Debian 8 template", which runs on a
xen-based VM, and is just a regular Debian with some additional packages
that allow the VMs based on this template to play nice on a Qubes OS system
(allowing copy&paste between machines, handle block device sharing, etc).

They way Qubes OS works in terms of networking is that "application VMs"
connect to internet through a "firewall VM", which has a WAN interface (the
insecure one) connected to a "network VM". At the end, from the point of
view of the VM I am reporting the issue from, it is like getting to the
Internet through a Linux-based firewall and then a home router.

Qubes templates have a tinyproxy-based proxy that allows the update of the
machines regardless of the firewall settings. Hence, they have the
Acquire::http::Proxy "http://10.137.255.254:8082/"; statement on their apt
config files. This proxy config seems quite generic:

User tinyproxy
> Group tinyproxy
> Port 8082
> Timeout 60
> DefaultErrorFile "/usr/share/tinyproxy/default.html"
> #StatHost "tinyproxy.stats"
> StatFile "/usr/share/tinyproxy/stats.html"
> Syslog On
> LogLevel Notice
> PidFile "/var/run/tinyproxy-updates/tinyproxy.pid"
> MaxClients 50
> MinSpareServers 2
> MaxSpareServers 10
> StartServers 2
> MaxRequestsPerChild 0
> DisableViaHeader Yes
> Allow 127.0.0.1
> Allow 10.137.0.0/16
> ConnectPort 443


I will monitor syslog when performing the apt-get update and see if I can
catch any special event.
So far, the same issue happens on my newer template, which is Debian
9-based, and is happening almost 50% of the time when the apt-lists are no
longer valid. When it happens, repeating the 'apt-get update' command
succeeds.

Thanks for pointing out this "small" detail.
Regards,
///Pablo

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