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Re: Jessie unable to update via squid proxy
Small bit of background. Wheezy has no problem at all using the proxy. Nor does Ubuntu, SUSE or Centos. Every Jessie install I have built has been unable to use the proxy. It basically stops at "Hit http://security.debian.org jessie/updates/main Translation-en" at "100% [Waiting for headers]"
The squid logs are not showing any issues. I have configured the proxy settings for apt in various ways depending on which article I am currently looking at. None so far have been able to correct the problem.
If I configure wgetrc to use the proxy, wget can successfully download the file. My current workaround is a list of systems which bypass the proxy altogether. This works fine but is not a long term solution by any stretch. So below are the various entries I have made so far in my attempts to configure apt 

/etc/apt/apt.conf

Acquire::http::Proxy "http://192.168.8.6:3128/";;
Acquire::https::Proxy "http://192.168.8.6:3128/";;
Acquire::ftp::Proxy "http://192.168.8.6:3128/";;

/etc/apt/apt.conf.d/01proxy

Acquire::http::Proxy "http://192.168.8.6:3128";;

/etc/apt/apt.conf.d/70debconf

// Pre-configure all packages with debconf before they are installed.
// If you don't like it, comment it out.
DPkg::Pre-Install-Pkgs {"/usr/sbin/dpkg-preconfigure --apt || true";};
Acquire::http::Proxy "http://192.168.8.6:3128";;

The squid access.log shows the following during an update
1485172349.591 19 192.168.10.98 TCP_MISS/404 454 GET http://ftp.uk.debian.org/debian/dists/jessie/InRelease - DIRECT/78.129.164.123 text/html 1485172349.598 6 192.168.10.98 TCP_REFRESH_UNMODIFIED/304 295 GET http://ftp.uk.debian.org/debian/dists/jessie-updates/InRelease - DIRECT/78.129.164.123 - 1485172349.621 4 192.168.10.98 TCP_REFRESH_UNMODIFIED/304 293 GET http://ftp.uk.debian.org/debian/dists/jessie/Release.gpg - DIRECT/78.129.164.123 - 1485172349.627 4 192.168.10.98 TCP_REFRESH_UNMODIFIED/304 295 GET http://ftp.uk.debian.org/debian/dists/jessie/Release - DIRECT/78.129.164.123 - 1485172349.648 6 192.168.10.98 TCP_REFRESH_UNMODIFIED/200 15785 GET http://ftp.uk.debian.org/debian/dists/jessie-updates/main/source/Sources.xz - DIRECT/78.129.164.123 application/octet-stream 1485172349.679 8 192.168.10.98 TCP_REFRESH_UNMODIFIED/200 7284 GET http://ftp.uk.debian.org/debian/dists/jessie-updates/main/binary-amd64/Packages.diff/Index - DIRECT/78.129.164.123 application/octet-stream 1485172349.687 8 192.168.10.98 TCP_REFRESH_UNMODIFIED/200 3071 GET http://ftp.uk.debian.org/debian/dists/jessie-updates/main/i18n/Translation-en.diff/Index - DIRECT/78.129.164.123 application/octet-stream 1485172349.697 8 192.168.10.98 TCP_MISS/416 316 GET http://ftp.uk.debian.org/debian/dists/jessie/main/source/Sources.xz - DIRECT/78.129.164.123 text/html 1485172349.806 233 192.168.10.98 TCP_REFRESH_UNMODIFIED/304 323 GET http://security.debian.org/dists/jessie/updates/InRelease - DIRECT/128.61.240.73 - 1485172349.937 102 192.168.10.98 TCP_REFRESH_MODIFIED/416 654 GET http://security.debian.org/dists/jessie/updates/main/source/Sources.bz2 - DIRECT/128.61.240.73 text/html 1485172350.043 105 192.168.10.98 TCP_REFRESH_MODIFIED/416 654 GET http://security.debian.org/dists/jessie/updates/main/binary-amd64/Packages.bz2 - DIRECT/128.61.240.73 text/html 1485172350.147 102 192.168.10.98 TCP_REFRESH_MODIFIED/416 654 GET http://security.debian.org/dists/jessie/updates/main/i18n/Translation-en.bz2 - DIRECT/128.61.240.73 text/html 1485172350.250 101 192.168.10.98 TCP_REFRESH_UNMODIFIED/304 324 GET http://security.debian.org/dists/jessie/updates/main/source/Sources.bz2 - DIRECT/128.61.240.73 - 1485172350.352 101 192.168.10.98 TCP_REFRESH_UNMODIFIED/304 324 GET http://security.debian.org/dists/jessie/updates/main/binary-amd64/Packages.bz2 - DIRECT/128.61.240.73 - 1485172350.454 101 192.168.10.98 TCP_REFRESH_UNMODIFIED/304 324 GET http://security.debian.org/dists/jessie/updates/main/i18n/Translation-en.bz2 - DIRECT/128.61.240.73 -
Before anyone points it out, we use a /22 so the system can resolve the proxy with no problems. 

Any pointers would be greatly appreciated.

Regards

Neil
Ok. Having seen this problem for about a year and a half, I have found a semi-solution. The problem only seems to affect ftp.uk.debian.org. If I change the repos to point to ftp.us.debian.org the problem magically goes away. Not tried any other locale. Still none the wiser as to what the real underlying problem is so any insights would still be very welcome.
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