I was on an airplane and tried to run the SIM Tool. To my surprise, I was greated with this error:
Application download did not succeed. Check your network connection, or contact your system administrator or network service provider.
Clicking the details button, this error was logged:
I understood that the SIM Tool tries to auto-update at startup. When dl.sitecore.net is unavailable or when offline, it refuses to even run.
The next time I had an Internet connection, I sniffed the network requests made by the SIM Tool to understand the process. To enable offline execution, I ended up creating a local website, setup IIS to serve it and modified my hosts file. This tricks the SIM Tool to believe the installed version is the latest version and enables the updater to succeed.
Basic Setup
Create a folder on your hard drive to store your local website. I named mine dl.sitecore.net.local.
When you know you will go offline for a certain period of time and you might need to use the SIM Tool, do the following:
Use Fiddler2 or another HTTP proxy to record the network requests made by the SIM Tool when starting.
Save the SIM.Tool.application file response body to the \dl.sitecore.net.local\updater\sim folder.
Inspect the request URL of the SIM.Tool.exe.manifest file. It is located in a folder like SIM.Tool_1_4_0_383 where the version number changes at each release.
Create this folder in your \dl.sitecore.net.local\updater\sim\Application Files folder. Your folder structure will look like: