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I have a server on the cloud in Asia. I installed squid proxy(It was http) on it and use it to browse my home country web pages. I sometimes use it to download content over the internet. Does each packet of my macbook pro go through the proxy if I set proxy in my computer settings? Can my ISP know the content I am downloading or the pages I am browsing if I use proxy?

When I open speedtest.net on browser with proxy settings on, it can detect my ISP. How does it do?

Follow up: I changed my proxy to https. So on my mac system network settings I connect to Secure Web Proxy(HTTPS) using xx.xxx.xxx.xxx:3128 where xx.xxx.xxx.xxx is my server ip address on which I installed squid proxy. My understanding is that when I open a website its packets(request packets) are sent to my proxy which then redirects them to the server. Do my requests to the website contain my ip address instead of my server ip address? If yes that's how my website can know my ip address. Since I connect to https proxy, can my ISP still read my requests? If I open xyz.com, can my ISP know that I opened xyz.com? Can DNS provider also know the websites I visit?

I am student at a US university and I asked this question out of curiosity and interest in knowing the working of networks rather than for any malicious purpose.

raju
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  • As the traffic over HTTP protocol goes as is, yes, they can. Because it's not encrypted. If have VPN on your tags, but proxy server aren't VPN. You can use VPN with encryption indeed, that way your ISP can't know what exactly you are accessing. They still can know you are using the VPN and the IP of your cloud. But not the content you are tunneling through it. – NStorm Sep 21 '17 at 05:52

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Firstly, your connection to the proxy can be monitored by your ISP.

Every packet will pass through your ISP then to your proxy except the sites you want to set as exception in Internet/LAN settings.

The connection from the proxy to the web you are trying to access can be hidden.

In the HTTP header, there's a field named x-forwarding which may be forwarding the original source IP to the web server you are visiting.

xeon
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  • With a small setting change in squid proxy I made it https. So my proxy url is https. – raju Sep 28 '17 at 17:43
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Proxy settings made under System preferences are system-wide. Note that your ISP and the server provider have the ability to inspect your traffic. Http traffic is easy to monitor, since it's not encrypted.

In any case your ISP knows the ip addresses (the proxy) you're contacting even if you start using encrypted connections (reason: their systems have to know where to direct your packages).

The ISP of the server in asia knows the addresses of the sites you use for the same reasons your local ISP knows the address of the proxy. Your local ISP has no jurisdiction to acquire this information from the server's ISP (it can however get the destination information from the packages you're sending to the proxy if you're not careful).

IP address ranges aren't dynamic in a sense that the ranges in use have been assigned to specific parties (ISPs, organizations). Using whois database it's possible to find out the ISP to whom a certain IP belongs to. This is probably what speedtest.net does.