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I have built a C#, .NET3.5, web application that installs a Windows service (run as the NetworkService user). This service acts as a specialised web server for any machine on the network, and the user connects to the service using their browser.

The whole thing is installed using an msi file built using Visual Studio 2008. The msi file installs and runs a deployment app, which is what deals with setting up users and permissions, and installing the exe as a service.

If I decide to enhance the app (or find and fix a bug), I can produce a new msi file, and get the user to run it on all the machines running my app. But I would rather that this happened automatically (including downloading the updates from my web site, and deploying them).

Because it runs as a service, it is not user-specific, so I understand Click Once deployment is not an option.

Is there any way for me to achieve this?

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If you really want no user interaction at all in the process, could you have a second service that is the update watchdog and identifies when a new version of the main service is available, and then handles the download/stop/install/start of the main service?

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Yes, I had thought of that. The second service would presumably have to run as the machine administrator, so it could overwrite the necessary files (and stop and restart services). Presumably that means I have to ask for the administrator password when installing it?
Well, in effect, you are asking for administrative rights already because you want to be able to re-install the service in the first place. I believe authentication is in the cards for this task regardless of how you accomplish it.
I have accepted this as an answer, even though I don't like it. Presumably I will have to ask the user for the admin password at install time, in order to create the admin service?
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Here is the solution I ended up with:

When installing the service, I gave the service user permission to start and stop the service. See my question on service permissions for more details.

The service program checks a remote url for a version file, and checks it against the current program version. If the version file is different, it downloads an update zip, extracts the update program from it, locks a file, runs the update program and immediately exits.

The update program locks the same file, waits a few seconds (just to make sure the service has stopped), unzips the zip (excluding the update program itself), and finally restarts the service.

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Here is the solution I am trying now:

There is a stub service, which does nothing else but check for an update program, run the update program, then run the main service program. If the main service program exits with a particular exit code, it loops round and repeats (otherwise it exits normally).

The main service program checks a remote url for a version file, and checks it against the current program version. If the version file is different, it downloads an update zip, extracts the update program from it, and exits with the special exit code.

The original installer gives the user account under which the service runs full permission to the program folder (so the update program can update the service program).

The only drawback is that it is impossible to update the stub service.

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