What is the definition of proxy-aware - proxy

I need clarification on the buzzword "Proxy-Aware". Does it mean that a proxy is sensed after the app attempts to directly perform a operation with a host? Or is it that after the creation of a proxy object (think .net WebProxy) and passing in proxy address, port, login etc.., the app knows how create and use the proxy connection to the server?

I think the word means if the application is able to establish connections to one or more proxy servers to reroute your connection attempt to target hosts through these proxy servers.
E.g. web browsers(proxy-aware) with proxy settings connects to the proxy server first and requests the proxy server to connect to your requested web page, but most terminal clients does not support proxy setting and can not perform such a process and thus are not proxy-aware.

After sifting through a few postings looking for a definition, I have come up with the definition for myself. "A proxy aware app is an app such that given a address (and/or creds) to a proxy as well as the destination address, the app will create the proxy connection and will manage the software side of the traffic between client, proxy connection and the destination." I conclude that a necessary condition to be a proxy-aware app is NOT the ability to sense a proxy but the ability to accept and manage the fact that there is an intermediate, addressable hop between client and destination.

Related

How can I make my Windows C++/OpenSSL application proxy-aware?

I'm working on a desktop C++ application which uses OpenSSL sockets (a raw TLS socket, not HTTPS) to communicate with our server.
One of our clients are required to route their traffic through a proxy. The client is using ZScaler in Tunnel with Local Proxy mode.
In theory, it's possible to reconfigure ZScaler to force our traffic through a proxy chosen by ZScaler. However, I want to investigate solutions where our application uses the Windows OS-level proxy settings rather than relying on ZScaler configuration.
I've read this post:
openssl s_client using a proxy
But I'm uncertain whether those answers apply to my situation, because that user didn't mention whether they're using Windows or Linux, and they appear to be talking about an HTTP/HTTPS proxy. Also, that question appears to be asking about the s_client function, rather than simply creating a TLS socket to my server through a "Tunnel with Local Proxy" on Windows.
So, my questions are:
Can OpenSSL be used to open an SSL socket to a server through Tunnel with Local Proxy?
Can we make an OS call to determine the IP/socket for the Tunnel with Local Proxy configuration?
If this is possible, then I have another question: suppose we have a single proxy at 10.100.10.0:5000.
If one user in our client's office opens a socket to our server via their proxy, will a 2nd user be unable to connect from their office because they're bottlenecked at single proxy socket?
Put another way: what is the standard way of implementing proxy-awareness for a Windows application using OpenSSL?
Note: This question was originally posted to Network Engineering stack exchange, but it was closed because it refers to an issue above OSI layer 4.
Note: I'm looking for a solution that does not require administrator permissions on the user PC. I would prefer for our application to discover and use OS-level proxy settings without making any administrative changes to the machine, i.e. by calling netsh.
Can OpenSSL be used to open an SSL socket to a server through Tunnel with Local Proxy?
OpenSSL doesn't do it for you but OpenSSL does not prevent it either. The tunnel has to be established before you do the TLS handshake to the endpoint. Depending on what kind of proxy this is you might need to use a HTTP CONNECT method for this or might need to use the SOCKS protocol or whatever your proxy requires. In case of ZScaler this is likely the HTTP CONNECT method but you need to make sure that the connection to the target IP and port is actually allowed by the security policy.
Once you've established the tunnel to the endpoint using the proxy you can just build the SSL socket on top of the TCP socket for the tunnel. Just do the usual SSL setup (i.e. SSL_new etc) and then associate the SSL object with the existing socket using SSL_set_fd. Then proceed as usual with the handshake, i.e. SSL_connect or similar.
Can we make an OS call to determine the IP/socket for the Tunnel with Local Proxy configuration?
I don't know but Winsock use system proxy settings might answer this part.
If one user in our client's office opens a socket to our server via their proxy, will a 2nd user be unable to connect from their office because they're bottlenecked at single proxy socket?
This should not be a problem. It is perfectly normal to have multiple connections through the proxy.

Send the request to Proxy server from Web server

I made a proxy server in python 3. It listens on the port 4444. It basically receives the request from clients and sends it to the server. I want to use it as a firewall to my Dvwa server. So added another functionality to the proxy. What it does is, before sending the request to the DVWA server, it validates the input.
But the problem is, the clients have to configure their proxy settings in the browser to use my proxy server. Is there any way to access the proxy without configuring the browser settings. Basically I want to host the proxy server instead of the original web server. So that all the traffic goes through the proxy before going to the webserver.
Thanks in advance...
You don't say whether your Python3 proxy is hosted on the same machine as the DVWA.
Assuming it is, the solution is simple: a reverse-proxy configuration. Your proxy transparently accepts and forwards requests to your server who then processes them and sends them back via the proxy to the client.
Have your proxy listen on port 80
Have the DVWA listen on a port other than 80 so it's not clashing (e.g. 8080)
Your proxy, which is now receiving requests for the IP/hostname which would otherwise go to the DVWA, then forwards them as usual.
The client/web browser is none the wiser that anything has changed. No settings need changing.
That's the best case scenario, given the information provided in your question. Unfortunately, I can't give any alternative solutions without knowing the network layout, where the machines reside, and the intent of the project. Some things to consider:
do you have a proper separation of concerns for this middleware you're building?
what is the purpose of the proxy?
is it for debugging/observing traffic?
are you actually trying to build a Web Application Firewall?

Does the protocol used by HTTP proxies reduce the number of connections negotiated by the client?

When an HTTP proxy server is used, is the number of connections negotiated between the client and the proxy reduced as compared to the client connecting directly to various http sites directly (without proxy)?
For example, when connecting directly to two different domains, it is clear that at least two connections must be made. In the case of a proxy, does the client usually use a single connect to the proxy for both "connections"?
Similarly, are there cases where a client that connecting to a single domain but accessing several resources would see a reduced number of connections using a proxy? E.g., can the proxy present a HTTP/1.1-style persistent connect even when the ultimate destination doesn't support it? Are proxies able to use longer persistent connection timeout periods?
In the case of a proxy, does the client usually use a single connect to the proxy for both "connections"?
While it would possible to use the same connection to a HTTP proxy to include HTTP requests to different targets most clients don't do it from what I've seen. Also, it would only work with HTTP and not HTTPS since in the latter case the whole TLS connection to the target is tunneled through the proxy and the close of this tunneled connection is also the close of the underlying TCP connection to the proxy. And, HTTP requests to multiple targets would only be possible with a HTTP proxy but not a SOCKS proxy since SOCKS essentially builds a tunnel to a specific target and this target is set at the beginning of the connection and can never be changed.
That said, while I've not seen it for browser to proxy connections I've seen a patched squid used (long ago) to do this in order to optimize proxy to proxy connections.
E.g., can the proxy present a HTTP/1.1-style persistent connect even when the ultimate destination doesn't support it?
While this would be possible too it is also not common. Usually the proxy does not fully decouple client and server, i.e. a server-triggered close of the connection between server and proxy usually results in close of the connection between proxy and client too. The reason is probably that it would work for only for HTTP anyway and not HTTPS and that it makes the implementation of the proxy more complex since things like repeating a request on sudden close of a persistent connection by the server between requests would now need to be handled by the proxy instead of simply forwarding the close and let the client deal with it.

How does the proxy mechanism work with proxy settings in browser

We often find columns like Address, Port in web browser proxy settings. I know when we use proxy to visit a page, the web browser request the web page from the proxy server, but what I want to know is how the whole mechanism works? I have observed that many ISP allow only access to a single IP(of their website) after we exhausted our free data usage. But when we enter the site which we wants to browse in proxy URL and then type in the allowed IP, the site get loaded. How this works?
In general, your browser simply connects to the proxy address & port instead of whatever IP address the DNS name resolved to. It then makes the web request as per normal.
The web proxy reads the headers, uses the "Host" header of HTTP/1.1 to determine where the request is supposed to go, and then makes that request itself relaying all remaining data in both directions.
Proxies will typically also do caching so if another person requests the same page from that proxy, it can just return the previous result. (This is simplified -- caching is a complex topic.)
Since the proxy is in complete control of the connection, it can choose to route the request elsewhere, scrape request and reply data, inject other things (like ads), or block you altogether. Use SSL to protect against this.
Some web proxies are "transparent". They reside on a gateway through which all IP traffic must pass and use the machine's networking stack to redirect outgoing connections to port 80 to a local port instead. It then behaves the same as though a proxy was defined in the browser.
Other proxies, like SOCKS, have a dedicated protocol that allows non-HTTP requests to be made as well.
There are 2 types of HTTP proxies, there are the ones that are reversed and the ones that
are forward.
The web browser uses a forward proxy, basically it is sending all http traffic through the proxy, the proxy will take this traffic out to the internet. Every http packet that comes out from your computer, will be send to the proxy before going to the target site.
The ISP blocking does not work when using a proxy because, every packet that comes out from your machine is pointing to the proxy and not to the targe site. The proxy could be getting internet through another ISP that has no blocks whatsoever.

Socks 4 Bind Request Explanation

i was reading this topic
http://ftp.icm.edu.pl/packages/socks/socks4/SOCKS4.protocol
and what im trying to do is:
i have a client/server application, what im trying to do is to use socks 4 BIND request to bind my server to a remote socks server, and make the clients connect to that socks server and the socks server will make them connect to my server (at least thats how i understand socks BIND request)
but i don't fully understand it (my English is kinda bad), what im asking is, is it possible to do so when i dunno any of the remote IPs of the clients? since the server's BIND request package must contain the address of the remote client and i dont really have than since the clients are from unknown users retrieving status info from my server (or can i use 0 for INANY_ADDR) ?
What you are asking for is not possible with SOCKS, nor is it meant for that purpose. Read the spec again more carefully. The BIND command is meant for use with multi-connection protocols (like FTP), where a primary connection is used to communicate between a client and a server, and BIND facilitates situations where the server needs to connect a secondary connection to the client after the client tells the server where to connect. In that situation, the client would issue a BIND command to SOCKS telling it the server's IP/Port so it only accepts that connection, then send the resulting SOCKS listening IP/Port to the server to connect to.
What you are asking for is better served by using a router with Port Forwarding rules defined. Then you can open a listening port on the router that accepts any inbound connection and forwards it to your app's listening IP/Port. Most modern routers support uPNP (Universal Plug-N-Play) so you can configure the forwarding rules programmably instead of requiring admin access to the router's configuration software.

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