Hey David, Just wondering if you have seen the apt related docs at: https://help.ubuntu.com/community/AptGet/Howto/#Setting_up_apt-get_to_use_a_http-proxy Eliezer From: squid-users <squid-users-bounces@xxxxxxxxxxxxxxxxxxxxx> On Behalf Of David Mills Sent: Wednesday, July 7, 2021 2:26 AM To: squid-users@xxxxxxxxxxxxxxxxxxxxx Subject: Ubuntu 20.04 "apt update" issues behind a VPN and Squid proxy Hi, We've got a collection of Ubuntu 18.04 boxes out in the field. They connect to an AWS OpenVPN VPN and use a Squid 3.5 AWS hosted Proxy. They work fine. We have tried upgrading one to 20.04. Same setup. From the command line curl or wget can happily download an Ubuntu package from the Ubuntu Mirror site we use. But "apt update" gets lots of "IGN:" timeouts and errors. The package we test curl with is https://mirror.aarnet.edu.au/ubuntu/pool/main/c/curl/curl_7.68.0-1ubuntu2.5_amd64.deb The Squid log shows a line the doesn't occur for the successful 18.04 "apt updates": 1625190959.233 81 10.0.11.191 TAG_NONE/200 0 CONNECT http://mirror.aarnet.edu.au:443 - HIER_DIRECT/2001:388:30bc:cafe::beef - The full output of an attempt to update is: Ign:1 https://mirror.aarnet.edu.au/ubuntu focal InRelease Ign:2 https://mirror.aarnet.edu.au/ubuntu focal-updates InRelease Ign:3 https://mirror.aarnet.edu.au/ubuntu focal-backports InRelease Ign:4 https://mirror.aarnet.edu.au/ubuntu focal-security InRelease Err:5 https://mirror.aarnet.edu.au/ubuntu focal Release Could not wait for server fd - select (11: Resource temporarily unavailable) [IP: 10.0.11.82 3128] Err:6 https://mirror.aarnet.edu.au/ubuntu focal-updates Release Could not wait for server fd - select (11: Resource temporarily unavailable) [IP: 10.0.11.82 3128] Err:7 https://mirror.aarnet.edu.au/ubuntu focal-backports Release Could not wait for server fd - select (11: Resource temporarily unavailable) [IP: 10.0.11.82 3128] Err:8 https://mirror.aarnet.edu.au/ubuntu focal-security Release Could not wait for server fd - select (11: Resource temporarily unavailable) [IP: 10.0.1.26 3128] Reading package lists... Done N: Ignoring file 'microsoft-prod.list-keep' in directory '/etc/apt/sources.list.d/' as it has an invalid filename extension E: The repository 'https://mirror.aarnet.edu.au/ubuntu focal Release' does not have a Release file. N: Updating from such a repository can't be done securely, and is therefore disabled by default. N: See apt-secure(8) manpage for repository creation and user configuration details. E: The repository 'https://mirror.aarnet.edu.au/ubuntu focal-updates Release' does not have a Release file. N: Updating from such a repository can't be done securely, and is therefore disabled by default. N: See apt-secure(8) manpage for repository creation and user configuration details. E: The repository 'https://mirror.aarnet.edu.au/ubuntu focal-backports Release' does not have a Release file. N: Updating from such a repository can't be done securely, and is therefore disabled by default. N: See apt-secure(8) manpage for repository creation and user configuration details. E: The repository 'https://mirror.aarnet.edu.au/ubuntu focal-security Release' does not have a Release file. N: Updating from such a repository can't be done securely, and is therefore disabled by default. N: See apt-secure(8) manpage for repository creation and user configuration details. While running, the line 0% [Connecting to HTTP proxy (http://vpn-proxy-d68aca8a8f7f81d6.elb.ap-southeast-2.amazonaws.com:3128)] appears often and hang for a while. I've tried upping the squid logging and allowing all, but they didn't offer any additional information about the issue. Any advice would be greatly appreciated. Regards, David Mills Senior DevOps Engineer E: mailto:david.mills@xxxxxxxxxxxxx M: +61 411 513 404 W:http://acusensus.com/ DISCLAIMER: Acusensus puts the privacy and security of its clients, its data and information at the core of everything we do. The information contained in this email (including attachments) is intended only for the use of the person(s) to whom it is addressed to, as it may be confidential and contain legally privileged information. If you have received this email in error, please delete all copies and notify the sender immediately. Any views or opinions presented are solely those of the author and do not necessarily represent the views of Acusensus Pty Ltd. Please consider the environment before printing this email. _______________________________________________ squid-users mailing list squid-users@xxxxxxxxxxxxxxxxxxxxx http://lists.squid-cache.org/listinfo/squid-users