Beren the 32nd: I'm certainly a lot more cautious about castling. The extra diagonal moving piece (Cardinal) lessens the advantage of moving your King to the flank. Plus the Cardinal himself is a very good piece at harrassing the King, especially when he can trap him in the corner. Other times it pays to castle if you can get the Rook into play. It's hard to combine castling and getting the Rook to the file you need him on. So often times I don't castle and just move the Rook. If you survive the middle game it's good to have your King centered, so this is one reason to not castle. It can be a long walk back to the other side from castling. I go along with SMIRF Engine and also add how you think the Pawns might look later in the game. If they're going to afford some protection from an attack, then castling towards them can help the defense.