Windows Update not working when connecting to system wide proxy

[sakshidalvi]

I was trying the checkpoint 3 Windows update bypass from user authentication. I set up the profiles in config as follow :



Authentication profile



I've bypassed windows update as per the question but when I use a system wide proxy and then try to use the windows update I get the following error :
In system wide proxy I am getting authentication for all apps such as cortana, internet explorer, chrome etc. but when I go to windows updates there is no authentication but I get the error. (0x80092013)




But when I disconnect from the proxy then I am able to get windows updates :

[aashish97]

Hello Sakshi,

As per your above Post I have analyzed that:
When the Proxy Settings is Done on Chrome (i.e. Windows System Wide Proxy Settings) and Proxy-Authentication is Enabled the Windows Updates Gives Error??

Yes, Windows Updates does not work when Proxy Authentication is Enabled.
Inorder to do that you will have to Bypass Windows Update from Proxy Authentication

Inorder to analyze the Root Cause of this Misconfiguration.
Please go through SafeSquid's Extended and Native

https://docs.safesquid.com/wiki/Analyze ... Squid_Logs

The Logs will help you understand the problem and create policies accordingly

[sakshidalvi]

Yes, Sir, I have bypassed the windows update request from proxy authentication as you can see in the screenshot. I've created a windows update profile in which windows update request is allowed.

screen 2.png (42.29 KiB) Viewed 2255 times

after that I've negated the profile from the authentication as follows :

screen 1.png (35.43 KiB) Viewed 2255 times

So that the authentication is not applied on the windows update profile.

[aashish97]

Inorder to analyze the Root Cause of this Misconfiguration.
Please go through SafeSquid's Extended and Native

https://docs.safesquid.com/wiki/Analyze ... Squid_Logs

The Logs will help you understand the problem and create policies accordingly

[sakshidalvi]

Here are the screenshots from the Extended (Detailed logs)

First when I was trying to use windows update the log entry was this here you can see that it showed that "proxy authentication required" :

access restriction log 1.png (24.95 KiB) Viewed 2252 times

access restriction log 2.png (40.87 KiB) Viewed 2252 times

After that I saw that the category was shown as "Unidentified Application and Unidentified Web 2.0" so I added the same categories of requests in the profile

new policy.png (35.36 KiB) Viewed 2252 times

[sakshidalvi]

Later when I ran after changing the categories I was able to bypass the proxy authentication as you can see in the logs :

without access restriction part 1.png (18.48 KiB) Viewed 2252 times

without access restriction part 2.png (26.58 KiB) Viewed 2252 times

But after that I was getting this error in the windows update(0x800b0109) which I think is not related to proxy issue but rather a windows update issue as you can see in the logs that authentication is bypassed for windows update:

new error.png (21.96 KiB) Viewed 2252 times

[aashish97]

Does the Window Updates work when Proxy is Not Configured?
Also Check Does the Window Updates work when Proxy is Configured But Authentication is Disabled Completely?

[sakshidalvi]

Windows update works completely fine when proxy is not configured.

When proxy is configured even after removing authentication windows update does not work and shows the same error (0x800b0109)

[aashish97]

Which means that Proxy Authentication is Not the Problem..
In this case, Please Go though the logs and and Gather Domains that Windows Updates Connect to,
Full Logging

Make sure you have enabled Debugging Log in SafeSquid

Check for errors
Attach the analysis and the logs for proper review

[sakshidalvi]

Sir I also tried removing all the policies and uploaded a blank config file still the error persists. The domain that Microsoft update is accessing are :

update domains.png (13.21 KiB) Viewed 2245 times