I just ran into an SQL Server database (2005 or 2008, I'm not sure) which had autogrowth set to "By 10 percent, unrestricted growth" on the primary data file. It had no free space, and inserts were failing because of lack of free space.
The drive had over 100 GB free, and the data file was about 15 GB. I wish I had kept the error message, but it was something about "insufficient free space on PRIMARY". It was not a timeout exception like I've seen on a few occasions with 2000, where it could take long periods of time to resize.
I increased the "Initial Size" setting by about 5 GB, and it completed instantly, and everything started working again after that.
Why does SQL Server sometimes not autogrow when it should?