Squid3-dev blocks Windows update and other updates

KOM

acl windowsupdate dstdomain windowsupdate.microsoft.com
acl windowsupdate dstdomain update.microsoft.com
acl windowsupdate dstdomain download.windowsupdate.com
…

Could you not just use .microsoft.com, .windowsupdate.com and .windows.com to replace all of that?

I've played with Squid3 dynamic caching with Windows Update and I always ended up in a situation where it would download the entire file for every segment it's trying to download. 100 MB of patches required downloading many gigabytes of data, as each segment request would cause the entire file to be downloaded again and again. My traffic graph would show my WAN being fully saturated for an hour or more and hardly anything coming in to LAN from Squid.

I have more than 70 pcs and i have to fix this urgently, any clue ?

For that many users, why not run WSUS?

Firzze

Hi, :)
So with ssl filtering, windows update does not want to do this. There in there a manipulation to do to solve this problem.
Sorry for my bad english ;D

Abhishek

I am also facing same issue as reported by poster , if any one have solution to this kindly update this thread ,if i bypass source Ip from proxy server settings i am able to update

aGeekhere

This was a main reason why I switch to a wpad.

Abhishek

@aGeekHere:

This was a main reason why I switch to a wpad.

So are you telling moving from transparent proxy to non transparent proxy will fix my issue ?

aGeekhere

I could not get windows updates to work through HTTPS/SSL interception, and dealing with the CA were a pain.

Windows updates using wpad with squid proxy works.

Abhishek

so u disabled Https interception ? i have no issue deploying cert since i am using AD gpmc

aGeekhere

You first have to decide if you want to use a transparent proxy or non transparent proxy with wpad

If you want to try using non transparent proxy with wpad here are a few links
https://doc.pfsense.org/index.php/WPAD_Autoconfigure_for_Squid
https://forum.pfsense.org/index.php?topic=93060.0

Note: non transparent proxy with wpad you disable HTTPS/SSL interception and Transparent HTTP proxy.

Let me know if you get stuck

Abhishek

So i cant use Https inspection with wpad ? As far as i understood wpad is a method of delivering proxy server info such as IP address and port number so we don't need to manually configure all client PC's proxy serttings manually in Non Transparent proxy case

IF using transparent proxy there is no need of configuring wpad

aGeekhere

So i cant use Https inspection with wpad

wpad is only used to auto configure a non transparent proxy.

transparent proxy there is no need of configuring wpad

You cannot have both.

KOM

So i cant use Https inspection with wpad ?

You can't use the HTTPS Interception feature of pfSense because it goes along with Transparent mode. If you use an explicit proxy (not transparent) and WPAD auto-detection, then you don't need to worry about certs or group policy. You will still be able to filter HTTPS streams and your users won't get a browser warning. The only glitch is that some mobiles, specifically Android, don't do WPAD so those users must manually configure the proxy.

S. Kirschner

The issue with the actual version of squid for pfsense is , that the acl "ssl::server_name" isnt available.

The available acl dstdomain shouldnt be used for that, because the information that dstdomain tries to compare are encrypted at these moment.

You could read the description http://lists.squid-cache.org/pipermail/squid-users/2015-July/004429.html

Another issue with Windows Update is , that Microsoft use self signed certificate that are not signed by VeriSign.
There would be 2 solutions for the 2nd issue , ignoring cert errors or import the certificate.

ramalave

Create Aliases Called add WindowsUpdate and the following list for the networking group
157.54.0.0/15
157.56.0.0/14
157.60.0.0/16
65.52.0.0/14
70.37.0.0/17
70.37.128.0/18
207.46.0.0/16
131.107.0.0/16
66.119.144.0/20
23.96.0.0/13
204.79.195.0/24
204.79.196.0/23
208.76.44.0/22
208.68.136.0/21
216.220.208.0/20
209.240.192.0/19
204.14.180.0/22
206.191.224.0/19
192.92.90.0/24
208.84.0.0/21
104.40.0.0/13
192.197.157.0/24
204.231.192.0/24
104.208.0.0/13
129.75.0.0/16
204.79.179.0/24
64.4.0.0/18
167.220.0.0/17
167.220.128.0/18
167.220.192.0/19
192.92.214.0/24
207.68.128.0/18
13.64.0.0/11
13.96.0.0/13
13.104.0.0/14
146.147.0.0/16
52.145.0.0/16
52.146.0.0/15
52.148.0.0/14
52.152.0.0/13
52.160.0.0/11
52.224.0.0/11
52.96.0.0/12
52.112.0.0/14
52.120.0.0/14
52.125.0.0/16
52.126.0.0/15
52.130.0.0/15
52.132.0.0/14
52.136.0.0/13
138.196.0.0/16
150.171.0.0/16
40.74.0.0/15
40.76.0.0/14
40.80.0.0/12
40.96.0.0/12
40.112.0.0/13
40.120.0.0/14
40.124.0.0/16
40.125.0.0/17
40.64.0.0/13
40.126.128.0/17
40.127.0.0/16
40.126.0.0/18
204.13.120.0/21
204.152.18.0/23
Then you go to Services –-> Squid Proxy Server ----> Bypass Proxy for These Destination IPs
Enter the created alliase called WindowsUpdate
And this way it fixes all the updates for Windows with Transparent Proxy

ramalave

Cria um Aliases chamado WindowsUpdate e você adicionar a lista de grupo de rede
157.54.0.0/15
157.56.0.0/14
157.60.0.0/16
65.52.0.0/14
70.37.0.0/17
70.37.128.0/18
207.46.0.0/16
131.107.0.0/16
66.119.144.0/20
23.96.0.0/13
204.79.195.0/24
204.79.196.0/23
208.76.44.0/22
208.68.136.0/21
216.220.208.0/20
209.240.192.0/19
204.14.180.0/22
206.191.224.0/19
192.92.90.0/24
208.84.0.0/21
104.40.0.0/13
192.197.157.0/24
204.231.192.0/24
104.208.0.0/13
129.75.0.0/16
204.79.179.0/24
64.4.0.0/18
167.220.0.0/17
167.220.128.0/18
167.220.192.0/19
192.92.214.0/24
207.68.128.0/18
13.64.0.0/11
13.96.0.0/13
13.104.0.0/14
146.147.0.0/16
52.145.0.0/16
52.146.0.0/15
52.148.0.0/14
52.152.0.0/13
52.160.0.0/11
52.224.0.0/11
52.96.0.0/12
52.112.0.0/14
52.120.0.0/14
52.125.0.0/16
52.126.0.0/15
52.130.0.0/15
52.132.0.0/14
52.136.0.0/13
138.196.0.0/16
150.171.0.0/16
40.74.0.0/15
40.76.0.0/14
40.80.0.0/12
40.96.0.0/12
40.112.0.0/13
40.120.0.0/14
40.124.0.0/16
40.125.0.0/17
40.64.0.0/13
40.126.128.0/17
40.127.0.0/16
40.126.0.0/18
204.13.120.0/21
204.152.18.0/23
Então você vai Services –-> Squid Proxy Server ----> Bypass Proxy for These Destination IPs
Escrevem os aliases criado chamado WindowsUpdate
e desta forma você pode atualizar todas as versões do Windows com proxy transparente

ramalave

Cria um Aliases chamado WindowsUpdate e você adicionar a lista de grupo de rede
157.54.0.0/15
157.56.0.0/14
157.60.0.0/16
65.52.0.0/14
70.37.0.0/17
70.37.128.0/18
207.46.0.0/16
131.107.0.0/16
66.119.144.0/20
23.96.0.0/13
204.79.195.0/24
204.79.196.0/23
208.76.44.0/22
208.68.136.0/21
216.220.208.0/20
209.240.192.0/19
204.14.180.0/22
206.191.224.0/19
192.92.90.0/24
208.84.0.0/21
104.40.0.0/13
192.197.157.0/24
204.231.192.0/24
104.208.0.0/13
129.75.0.0/16
204.79.179.0/24
64.4.0.0/18
167.220.0.0/17
167.220.128.0/18
167.220.192.0/19
192.92.214.0/24
207.68.128.0/18
13.64.0.0/11
13.96.0.0/13
13.104.0.0/14
146.147.0.0/16
52.145.0.0/16
52.146.0.0/15
52.148.0.0/14
52.152.0.0/13
52.160.0.0/11
52.224.0.0/11
52.96.0.0/12
52.112.0.0/14
52.120.0.0/14
52.125.0.0/16
52.126.0.0/15
52.130.0.0/15
52.132.0.0/14
52.136.0.0/13
138.196.0.0/16
150.171.0.0/16
40.74.0.0/15
40.76.0.0/14
40.80.0.0/12
40.96.0.0/12
40.112.0.0/13
40.120.0.0/14
40.124.0.0/16
40.125.0.0/17
40.64.0.0/13
40.126.128.0/17
40.127.0.0/16
40.126.0.0/18
204.13.120.0/21
204.152.18.0/23
Então você vai Services –-> Squid Proxy Server ----> Bypass Proxy for These Destination IPs
Escrevem os aliases criado chamado WindowsUpdate
e desta forma você pode atualizar todas as versões do Windows com proxy transparente

blueadept

ramalave's solution worked fine for me.

AndrewGR

@ramalave , thanks for the list of networks. It helped in my case as well with squid in transparent mode.
Are there any other solutions available to fix Windows Updates issues when squid works in transparent mode?
Thanks!