Does http CONNECT method get proxy relay data at TCP level? - http

This is the question about HTTP CONNECT method.
I learned that after CONNECT request from client a TCP connection is established between proxy and remote server.
Then, at the step of SSL handshake, does the proxy evaluate and relay any http data from client up to at TCP level? So the data is not passed to application level of the proxy?
I understood that after SSL session establishment any data from client is encrypted and the proxy cannot read those. But how about the time before SSL session establishment, that is, SSL handshake step?

After the proxy has sent a successful response to the clients CONNECT request a normal proxy will forward all data between client and server without any changes. This includes the TLS handshake for HTTPS connections tunneled using CONNECT.
Note that there are proxies which do SSL interception (typically at firewalls). In this case the data are not blindly forwarded but the proxy will be an active man in the middle which means that the client does not receive the original certificate from the server and that the proxy will decrypt and maybe even modify the traffic between client and server.

Related

Close HTTP request socket connection

I'm implementing HTTP over TLS proxy server (sni-proxy) that make two socket connection:
Client to ProxyServer
ProxyServer to TargetServer
and transfer data between Client and TargetServer(TargetServer detected using server_name extension in ClientHello)
The problem is that the client doesn't close the connection after the response has been received and the proxy server waits for data to transfer and uses resources when the request has been done.
What is the best practice for implementing this project?
The client behavior is perfectly normal - HTTP keep alive inside the TLS connection or maybe even a Websocket connection. Given that the proxy does transparent forwarding of the encrypted traffic it is not possible to look at the HTTP traffic in order to determine exactly when the connection can be closed. A good approach is therefore to keep the connection open as long as the resources allow this and on resource shortage close the connections which were idle (no traffic) the longest time.

Can you use Keep-Alive with a CONNECT request with an HTTP proxy?

I know that with HTTP/1.1 proxies, it's possible to use Keep-Alive to keep a persistent connection with the proxy and from the proxy to the remote server, but I'm curious if/how that would work with an HTTPS connection. I know that to do this, the browser sends a CONNECT request to the proxy to establish a connection then begins communicating using HTTPS. I'm curious if it's possible to use Keep-Alive with HTTPS through an http proxy.
Simply put, CONNECT is always keep-alive.
In HTTP, “persistent connection” means a connection that persists after one request-response pair. But CONNECT establishes a tunnel through the proxy. The proxy cannot even see the requests and responses that are sent over this tunnel (because they are encrypted). So there is no way for this tunnel to not be persistent.
Of course, if the server (the target of CONNECT) decides to close the connection, then the tunnel is destroyed, too. So the server must support persistent connections (just as with a regular, non-TLS proxy).

WebSockets - why is the handshake HTTP? Sharing port 80

I'm not clear why the handshake for WebSocket is HTTP. Wiki says "The handshake resembles HTTP so that servers can handle HTTP connections as well as WebSocket connections on the same port." What is the benefit of this? Once you start communicating over WebSocket you are using port 80 also...so why can't the initial handshake be in WebSocket format?
Also, how do you have both WebSocket and HTTP servers listening on port 80? Or is it typically the same application functioning as HTTP and WebSocket servers?
Thanks y'all :)
WebSockets are designed to work almost flawlessly with existing web infrastructures. That is the reason why WS connections starts as HTTP and then switches to a persistent binary connection.
This way the deployment is simplified. You don't need to modify your router's port forwarding and server listen ports... Also, because it starts as HTTP it can be load balanced in the same way that a normal HTTP request, firewalls are more lean to let the connection through, etc.. etc... Last but not the least, the HTTP handshake also carry cookies, which it is great to integrate with the rest of the app in the same way that AJAX does.
Both, traditional HTTP request-response and WS, can operate in the same port. Basiclally the WS client sends a HTTP request asking for "Upgrade:websocket", then if the server accepts the WS connections, replies with a HTTP response indicating "101 Switching Protocols", from that point the connection remains open and both ends consider it as a binary connection.

Why are HTTP proxies able to support protocols like IRC and FTP?

I understand that a SOCKS proxy only establishes a connection at the TCP level while an HTTP proxy interprets traffic at HTTP level. Thus a SOCKS proxy can work for any kind of protocol while an HTTP Proxy can only handle HTTP traffic. But why does an HTTP Proxy like Squid can support protocol like IRC, FTP ? When we use an HTTP Proxy for an IRC or FTP connection, what does specifically happen? Is there any metadata added to the package when it is sent to the proxy over the HTTP protocol?
HTTP proxy is able to support high level protocols other than HTTP if it supports CONNECT method, which is primarily used for HTTPS connections, here is description from Squid wiki:
The CONNECT method is a way to tunnel any kind of connection through an HTTP proxy. By default, the proxy establishes a TCP connection to the specified server, responds with an HTTP 200 (Connection Established) response, and then shovels packets back and forth between the client and the server, without understanding or interpreting the tunnelled traffic
If client software supports connection through 'HTTP CONNECT'-enabled (HTTPS) proxy it can be any high level protocol that can work with such a proxy (VPN, SSH, SQL, version control, etc.)
As others have mentioned, the "HTTP CONNECT" method allows you to establish any TCP-based connection via a proxy. This functionality is needed primarily for HTTPS connections, since for HTTPS connections, the entire HTTP request is encrypted (so it appears to the proxy as a "meaningless" TCP connection). In other words, an HTTPS session over a proxy, or a SSH/FTPS session over a proxy, will both appear as "encrypted sessions" to the proxy, and it won't be able to tell them apart, so it has to either allow them all or none of them.
During normal operation, the HTTP proxy receives the HTTP request, and is "smart enough" to understand the request to be able to do high level things with it (e.g. search its cache to see if it can serve the response without going to the destination server, or consults a whitelist/blacklist to see if this URL is allowed, etc.). In "CONNECT" mode, none of this happens. The proxy establishes a TCP connection to the destination server, and simply forwards all traffic from the client to the destination server and all traffic from the destination server to the client. That means any TCP protocol can work (HTTPS, SSH, FTP - even plain HTTP)

Pros and cons of using a Http proxy v/s https proxy?

The JVM allows proxy properties http.proxyHost and http.proxyPort for specifying a HTTP proxy server and https.proxyHost and https.proxyPort for specifying a HTTPS proxy server .
I was wondering whether there are any advantages of using a HTTPS proxy server compared to a HTTP proxy server ?
Is accessing a https url via a HTTPS proxy less cumbersome than accesing it from a HTTP proxy ?
HTTP proxy gets a plain-text request and [in most but not all cases] sends a different HTTP request to the remote server, then returns information to the client.
HTTPS proxy is a relayer, which receives special HTTP request (CONNECT verb) and builds an opaque tunnel to the destination server (which is not necessarily even an HTTPS server). Then the client sends SSL/TLS request to the server and they continue with SSL handshake and then with HTTPS (if requested).
As you see, these are two completely different proxy types with different behavior and different design goals. HTTPS proxy can't cache anything as it doesn't see the request sent to the server. With HTTPS proxy you have a channel to the server and the client receives and validates server's certificate (and optionally vice versa). HTTP proxy, on the other hand, sees and has control over the request it received from the client.
While HTTPS request can be sent via HTTP proxy, this is almost never done because in this scenario the proxy will validate server's certificate, but the client will be able to receive and validate only proxy's certificate, and as name in the proxy's certificate will not match the address the socket connected to, in most cases an alert will be given and SSL handshake won't succeed (I am not going into details of how to try to address this).
Finally, as HTTP proxy can look into the request, this invalidates the idea of security provided by HTTPS channel, so using HTTP proxy for HTTPS requests is normally done only for debugging purposes (again we omit cases of paranoid company security policies which require monitoring of all HtTPS traffic of company employees).
Addition: also read my answer on the similar topic here.
There are no pros or cons.
And there are no "HTTPS proxy" server.
You can tell the protocol handlers which proxy server to use for different protocols. This can be done for http, https, ftp and socks. Not more and not less.
I can't tell you if you should use a different proxy for https connections or not. It depends.
I can only explain the difference of an http and https request to a proxy.
Since the HTTP Proxy (or web proxy) understands HTTP (hence the name), the client can just send the request to the proxy server instead of the actual destenation.
This does not work for HTTPS.
This is because the proxy can't make the TLS handshake, which happens at first.
Therefore the client must send a CONNECT request to the proxy.
The proxy establishes a TCP connection and just sends the packages forth and back without touching them.
So the TLS handshake happens between the client and destenation.
The HTTP proxy server does not see everything and does not validate destenation servers certificate whatsoever.
There can be some confusion with this whole http, https, proxy thing.
It is possible to connect to a HTTP proxy with https.
In this case, the communication between the client and the proxy is encrypted.
There are also so called TLS terminating or interception proxy servers like Squid's SSL Peek and Splice or burp, which see everything.
But this should not work out of the box, because the proxy uses own certificates which are not signed by trusted CAs.
References
https://docs.oracle.com/javase/8/docs/technotes/guides/net/proxies.html
https://parsiya.net/blog/2016-07-28-thick-client-proxying---part-6-how-https-proxies-work/
http://dev.chromium.org/developers/design-documents/secure-web-proxy
https://www.rfc-editor.org/rfc/rfc2817#section-5
https://www.rfc-editor.org/rfc/rfc7231#section-4.3.6
If you mean connecting to a HTTP proxy server over TLS by saying HTTPS proxy, then
I was wondering whether there are any advantages of using a HTTPS
proxy server compared to a HTTP proxy server ?
The advantage is that your client's connection to proxy server is encrypted. E.g. A firewall can't not see which host you use CONNECT method connect to.
Is accessing a https url via a HTTPS proxy less cumbersome than
accesing it from a HTTP proxy ?
Everything is the same except that with HTTPS proxy, brower to proxy server connection is encrypted.
But you need to deploy a certificate on your proxy server, like how a https website does, and use a pac file to configure the brower to enable Connecting to a proxy over SSL.
For more details and a practical example, check my question and answer here HTTPs proxy server only works in SwitchOmega
Unfortunately, "HTTPS proxy" has two distinct meanings:
A proxy that can forward HTTPS traffic to the destination. This proxy itself is using an HTTP protocol to set up the forwarding.
In case the browser is trying to connect to a website using HTTPS, the browser will send a CONNECT request to the proxy, and the proxy will set up a TCP connection with the website and mirror all TCP traffic sent on the connection from the browser to the proxy onto the connection between the proxy and the website, and similarly mirror the response TCP packet payload from the webite to the connection with the browser. Hypothetically, the same mechanism using CONNECT could be used with HTTP traffic, but practically speaking browsers don't do that. For HTTP traffic, they send the actual HTTP request to the proxy, including the full path in the HTTP command (as well as setting the Host header): https://stackoverflow.com/a/38259076/10026
So, by this definition, HTTPS Proxy is a proxy that understands the CONNECT directive and can support HTTPS traffic going between the browser and the website.
A proxy that uses HTTPS protocol to secure client communication.
In this mode (sometimes referred to as "Secure Proxy"), the browser uses the proxy's own certificate to perform TLS handshake with the proxy, and then sends either HTTP or HTTPS traffic, (including CONNECT requests), on that connection as per (1). So, the connection between the browser and the proxy is always protected with a TLS key derived using the proxy's certificate, regardless of whether the traffic itself is encrypted with a key negotiated between the browser and the website. If HTTPS traffic is proxied via a secure proxy, it is double-encrypted on the connection between the browser and the proxy.
For example, the Proxy Switcher Chrome plugin has two separate settings to control each of these funtionalities:
As of 2022, the option to use a secure proxy is not available in MacOS and Windows manual proxy configuration UI. But a secure proxy may be specified in a PAC file used in automatic proxy configuration using the HTTPS proxy directive. It is up to the consuming application to support the HTTPS directive; most major browsers, except Safari, and many desktop apps support it.
NOTE: Things get a bit more complicated because some proxies that proxy HTTPS traffic don't simply forward TCP packet payload, as described in (1), but act as Intercepting Proxies. Using a spoofed website certificate, they effectively perform a Man-in-the-Middle attack (well, it's not necessarily an attack because it's expected behavior). Whereas the browser thinks it's using the website's certificate to set up a TLS tunnel with a website, it's actually using a spoofed certificate to set up TLS tunnel with the proxy, and the proxy sets up the TLS tunnel with the website. Then proxy has visibility into the HTTPS requests/responses. But all of that is completely orthogonal to whether the proxy is acting as a secure proxy as per (2).

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