Of the many things that you have to consider, one of the biggest will have to be your own knowledge. Since this application will be making modifications to the network connections and resources you need to be sure you know what you are doing.

If you are not familiar with it, you should study first. Even the freeware versions are feature rich, and if you do not know the difference between a UDP port mapper and a caching DNS, do not install the software until you understand the terms. If you are on a LAN, let the system administrator or network supervisor download the proxy server for Windows or ask for directions if you are not sure.

The other element that will come into play will be the elements of the software itself. A lot of them have features that you may or may not need. Think about what you or your network requires. Do you need widespread support for various protocols? Then it must be compatible with SMTP proxy, POP3, SOCKS, http, https. tcpm, etc.

If you must facilitate and manage the user access, you will want an application that can manipulate bandwidth, modify and monitor traffic, syslog, ODBC functions, and others. You might also want to see if the application supports multiple platforms just in case you need to access other files.

Of course, a proxy server for Windows needs to specify just what type of Windows it can run on. If you are using Vista or XP, you must download one that supports it. Installing and using a software not compatible with the operating system can have disastrous consequences. As for the price, that is something that will concern the administrator. But if you are running a standalone computer, or the decision is yours to make, you should look at the features first and foremost.

What this means is that just because it is free does not mean that it is of low quality, but you must also recognize a situation wherein you might have to pay some money to get the best proxy server for Windows for your system. Once you have addressed all these issues, downloading and installing the right application will be less stressful.