We see the same behaviour with 10.04.3 Lucid "Clients" (with backports &
proposed updates enabled) using a "regular" squid3 proxy server

-------------------cut--------------
root@backup:~# dpkg -l apt
Desired=Unknown/Install/Remove/Purge/Hold
| Status=Not/Inst/Cfg-files/Unpacked/Failed-cfg/Half-inst/trig-aWait/Trig-pend
|/ Err?=(none)/Reinst-required (Status,Err: uppercase=bad)
||/ Name                                            Version                     
                    Description
+++-===============================================-===============================================-==============================================================================================================
ii  apt                                             0.7.25.3ubuntu9.9           
                    Advanced front-end for dpkg

root@backup:~# cat /etc/apt/apt.conf.d/99proxy 
Acquire::http::Proxy "http://dhcp.office.XXX.de:3128";;


root@dhcp:~# dpkg -l squid3
Desired=Unknown/Install/Remove/Purge/Hold
| Status=Not/Inst/Cfg-files/Unpacked/Failed-cfg/Half-inst/trig-aWait/Trig-pend
|/ Err?=(none)/Reinst-required (Status,Err: uppercase=bad)
||/ Name                                            Version                     
                    Description
+++-===============================================-===============================================-==============================================================================================================
ii  squid3                                          3.0.STABLE19-1ubuntu0.1     
                    A full featured Web Proxy cache (HTTP proxy)

root@dhcp:~# egrep -v '^(#|$)' /etc/squid3/squid.conf 
acl manager proto cache_object
acl localhost src 127.0.0.1/32
acl to_localhost dst 127.0.0.0/8 0.0.0.0/32
acl localnet src 192.168.219.0/24       # RFC1918 possible internal network
acl localnet src 192.168.220.0/23       # RFC1918 possible internal network
acl localnet src 192.168.230.0/24       # RFC1918 possible internal network
acl localnet src 192.168.232.0/23       # RFC1918 possible internal network
acl SSL_ports port 443
acl Safe_ports port 80          # http
acl Safe_ports port 21          # ftp
acl Safe_ports port 443         # https
acl Safe_ports port 70          # gopher
acl Safe_ports port 210         # wais
acl Safe_ports port 1025-65535  # unregistered ports
acl Safe_ports port 280         # http-mgmt
acl Safe_ports port 488         # gss-http
acl Safe_ports port 591         # filemaker
acl Safe_ports port 777         # multiling http
acl CONNECT method CONNECT
http_access allow manager localhost
http_access deny manager
http_access deny !Safe_ports
http_access deny CONNECT !SSL_ports
http_access deny to_localhost
http_access allow localnet
http_access allow localhost
http_access deny all
icp_access deny all
htcp_access deny all
http_port 3128
hierarchy_stoplist cgi-bin ?
cache_mem 200 MB
maximum_object_size_in_memory 10240 KB
cache_replacement_policy heap LFUDA
cache_dir ufs /var/spool/squid3 8192 16 256
maximum_object_size 512 MB
access_log /var/log/squid3/access.log squid
refresh_pattern -i .udeb$       129600  100%    129600
refresh_pattern -i .deb$        129600  100%    129600
refresh_pattern -i .rpm$        129600  100%    129600
refresh_pattern -i .tgz$        129600  100%    129600
refresh_pattern -i .gz$         129600  100%    129600
refresh_pattern -i .bz2$        129600  100%    129600
refresh_pattern -i .exe$        129600  100%    129600
refresh_pattern -i .cab$        129600  100%    129600
refresh_pattern -i .img$        129600  100%    129600
refresh_pattern ^ftp:           1440    20%     10080
refresh_pattern ^gopher:        1440    0%      1440
refresh_pattern (cgi-bin|\?)    0       0%      0
refresh_pattern .               0       20%     4320
icp_port 3130
coredump_dir /var/spool/squid3
-------------------cut--------------

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https://bugs.launchpad.net/bugs/915246

Title:
  update-manager could detect transparent proxy to avoid "Hash Sum
  mismatch" errors

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