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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


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