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Currently, I have Steam set to start automatically in Big Picture Mode when my Windows 8 machine boots. The idea is that this computer will mostly be used for gaming, so it is a good default. Part of my ideal experience is that I will be automatically logged and brought directly to my library of games.

This is mostly accomplished. The only catch is that when I do not have network access (rare, but sometimes the case), Steam does not automatically logged me in. Instead, it feels the needs to ask me whether to try again, or whether to log in using offline mode.

Is there a way to have Steam automatically log in using offline mode, but only if there is no network access?

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Playing around with Steam offline mode is somewhat tricky, since it sometimes just won't work. Anyway, you can create a local copy of the steam.cfg file with the following settings in it:

BootStrapperInhibitAll=enable
BootStrapperForceSelfUpdate = disable
ForceOfflineMode=enable

Put the newly created steam.cfg file in your Steam directory and it should start in offline mode.

Doing it automatically based on your internet connection may be possible, if you know how to achieve this using a Batch file. This would be something for Stackoverflow, though.

The steps you'd need to do:

  1. Create the mentioned config file as somethingelse.txt inside your Steam directory.
  2. Check for connectivity (maybe use this answer from SO).
  3. If offline, put the steam.cfg mentioned above in place:
    • Have your steam.cfg file ready, but under a different name, that's why I called it somethingelse.txt.
      (If it's there, Steam is offline. Period.)
    • RENAME somethingelse.txt steam.cfg
  4. If online, do (almost) nothing.
    • Remove/rename existing steam.cfg file, if it's still present from a previous session.
  5. Start Steam.

You could achieve this by using a single Batch file (the one in 1.), but it's not as easy as it looks.

Starting Steam directly in online mode without the Batch file would still require you to look for the presence of the steam.cfg file, unless you're sure it's not there or at least renamed. No steam.cfg, no harm.

Disclaimer:
This answer covers only how to actually get into offline mode forcefully. If you didn't install, update & save your games properly you can not play them in offline mode. If you didn't save your login credentials (and exit Steam gracefully) you can not use the offline mode at all. Make sure to test everything while still being connected to the internet.

Also if your settings get saved even with having the file removed, just revert them (ForceOfflineMode=disable) and keep them as new steam.cfg file for the next launch.

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