Sometimes, when I add a new column to a document library, and I save a file in that document library from within an app, it will pop up a window and ask for the values.  However, sometimes it doesn't.

For example, if I save a document into a document library with added columns from Word, it will ask for the extra properties.  But saving a file to the same document library from Outlook or IE, and it does not.

I'm guessing this is either as-designed or the functionality either is not OS-driven or just plain hasn't made it into the Outlook/IE featuresets.  Either way, if anyone knows otherwise or can recommend tweaks to enable this prompting of information more often, I'd appreciate it.