The question What information is sent to Wolfram Research when loading or working with Mathematica? describes the information sent to Wolfram's servers in routine Mathematica usage (Documentation Center/Wolfram|Alpha/Paclet updates etc).
Apparently you can assume that the following is sent to Wolfram's Servers
- All your search terms used in the Documentation Center
- IP Number
$Version$SystemID$LicenseID$MachineID
But what about when sending a generic web query using URLExecute, Import etc. to any server? What information is sent and can you modify it to attain "Tor-like" anonymity?
Some Background:
Settings for a web-query can be wrapped in a HTTPRequest which includes a "UserAgent" setting that is by default the "Wolfram HTTPClient xxxx" (where xxxx is a version number). This "UserAgent" seems to carry information about the operating system and of course indicates that it emanates from Mathematica. There isn't a way of spoofing the IP number in the HTTPRequest wrapper as pointed out by Carl Lange in the comments but this can potentially be done by
- Setting the
"UserAgent"key inHTTPRequestto apply that"UserAgent"'s proxy settings. - Adding proxy settings in the Proxy Dialog found in Mathematica's Preferences.
As per the documentation by default on Windows the proxy settings are taken from browsers while on a Mac they are taken from the Network Preferences panel.
Another alternative might be to just use browser proxies by restricting to WebExecute

"UserAgent"was simply an attempt to see if Mathematica can piggy-back off its proxy handling to ensure online anonymity. I will edit the question to clarify. – Saunter Dec 02 '19 at 23:11URLExecutesat it. – Carl Lange Dec 03 '19 at 00:46Importfunctionality and an emphasis on understanding identifying information sent. – Saunter Dec 03 '19 at 02:21