I know there are plenty of questions here already about this topic (I've read through as many as I could find), but I haven't yet been able to figure out how best to satisfy my particular criteria. Here are the goals: The ASP.NET application will run on a few different web servers, including localhost workstations for development. This means encrypting web.config using a machine key is out. The application will decide which connection string to use based on the server name (using a switch statement). For example, "localhost" and "dev.example.com" will use the DevDatabaseConnectionString, "test.example.com" will use the TestDatabaseConnectionString, and "www.example.com" will use the ProdDatabaseConnectionString, for example. Ideally, the exact same executables and web.config should be able to run on any of these environments, without needing to tailor or configure each environment separately every time that we deploy (something that seems like it would be easy to forget/mess up one day during a deployment, which is why we moved away from having just one connectionstring that has to be changed on each target). Deployment is currently accomplished via FTP. We will not have command-line access to the production web server. This means using aspnet_regiis.exe is out. (I could run on localhost, however, if this would still work.) We would prefer to not have to recompile the application whenever a password changes, so using web.config (or db.config or whatever) seems to make the most sense. A developer should not be able to decrypt the production database password. If a developer checks the source code out onto their localhost laptop (which would determine that it should be using the DevDatabaseConnectionString, remember?) and the laptop gets lost or stolen, it should not be possible to get at the other connection strings. Thus, having a single RSA private key to un-encrypt all three passwords cannot be considered. (Contrary to #3 above, it does seem like we'd need to have three separate key files if we went this route; these could be installed once per machine, and should the wrong key file get deployed to the wrong server, the worst that should happen is that the app can't decrypt anything---and not allow the wrong host to access the wrong database!) I know this is probably a subjective question (asking for a "best" way to do something), but given the criteria I've mentioned, I'm hoping that a single best answer will indeed arise. Thank you!