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.