Hello Debian users,

I'm experimenting with Debian in an enterprise environment. We have a corp. 
Internet proxy which downloads and scans files prior to passing the files onto 
the client. 

With Debian this seems to be a problem for APT. I am able to run 'apt-get 
update' and that seems to work OK, however when I try to actually run 'apt-get 
upgrade' on Debian 10 it tries for a few seconds to download a patch for: 
'linux-image-4.19.0-5-amd64', which is 47.6MB. It tries and gives up fairly 
quickly. 

       # apt-get upgrade
       Reading package lists... Done
       Building dependency tree
       Reading state information... Done
       Calculating upgrade... Done
       The following packages will be upgraded:
         linux-image-4.19.0-5-amd64
       1 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
       Need to get 47.6 MB of archives.
       After this operation, 3,072 B disk space will be freed.
       Do you want to continue? [Y/n] y
       Get:1 http://cdn-fastly.deb.debian.org/debian-security 
buster/updates/main amd64 linux-image-4.19.0-5-amd64 amd64 4.19.37-5+deb10u2 
[47.6 MB]
       Err:1 http://cdn-fastly.deb.debian.org/debian-security 
buster/updates/main amd64 linux-image-4.19.0-5-amd64 amd64 4.19.37-5+deb10u2
         Undetermined Error [IP: x.x.x.x]
E: Failed to fetch 
http://cdn-fastly.deb.debian.org/debian-security/pool/updates/main/l/linux-signed-amd64/linux-image-4.19.0-5-amd64_4.19.37-5+deb10u2_amd64.deb
  Undetermined Error [IP: x.x.x.x]
       E: Unable to fetch some archives, maybe run apt-get update or try with 
--fix-missing?

I have tried to search Google to find a way to significantly increase the 
timeout that APT has or the number of retries without any success, but I fear I 
may be doing it wrong. Here is my apt.conf:

       # cat /etc/apt/apt.conf
       Acquire::http::Proxy "http://proxy.domain.tld:80";;
       Acquire::http::Timeout "999";
       Acquire::https::Timeout "999";
       APT::Acquire::Retries "5";

Anyone have any experience with forcing Debian's APT to try very hard and for a 
long time while doing downloads/upgrades? If it matters I'm running Debian 10 
AMD64 on VMware vSphere.

Thanks,


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