[squid-users] Ubuntu 20.04 "apt update" issues behind a VPN and Squid proxy

[David Mills]

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
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: david.mills at acusensus.com

 M: +61 411 513 404

 W: acusensus.com

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