So, I recently (about 4 months ago) decided that my US Luggage briefcase was too big, allowing me to pack too much stuff into it and consequently hurting my shoulder.

Rooting around, I found an unused Dell laptop bag that came with my computer that would work nicely. It's large enough to take the stuff I need, yet small enough that I can't bring all kinds of extra crap that I never use. I've been meaning to replace it with a nicer one, but I never got around to it.

The problem, though, is that there is something wrong with my new briefcase. It is apparently quite dangerous. In my last ten trips through the Invincible Kingdom of Securityland, my briefcase has been flagged for a thorough search nine times. Eight times, the screener has removed every single item. With my previous bag, this hardly ever happened. Maybe once in ten trips.

So what gives? My standard carry-on fare includes a computer, the AC-plug, my Bose headphones, a flashlight with spare batteries, keys, a phone, two or three books, a MP3 player, assorted coins, a couple DVDs, and my sunglasses.

I brought the same load of junk in my old bag, yet I never had problems with security. This has happened, so far, in PHL, EWR, SEA, ANC, and FAI.

Just speculation, but it's possible that the smaller bag compacts the items inside of it to a degree where the x-ray can't get a good scan - a coin, for example, isn't opaque. Five bucks worth of pennies all in a little change purse, however, is opaque.

Yeah. Pre 9/11 the only time I got searched at X-ray was when I had a very lightly-packed carryon. It was an emergency trip, I had simply thrown what I needed in a rollaboard and didn't worry about arrangement. Everything electronic ended up in a mass. I've carried virtually the same stuff (leaving out only the cord for my shaver--if I know it's charged I don't need it for a trip less than weeks.) other times with no problem but it's been arranged better.

Your bag contains a brick shaped mass of organic material, wires, batteries, coupled with several potential timers and detonators. You take all that and put it in a suitcase which probably lines up everything nicely.

I would honestly be more concerned if your bag wasn't getting checked.

I guess what I don't understand is why the larger bag was less suspicuous. I suppose I can believe that the smaller bag, making everything more condensed, must have something to do with it.

Organic material? You mean my books?

Yup!

Does this dell bag have the huge round solid metal closure? I know that if it is opaque they are suppose to check behind it.

Yea, definitely just pushes stuff together where the TSO can't see anything.

I'd pull the flashlight and books out. Maybe the AC cord, depending on how it looks. Put them in another bin. See if that works. Should save you time and that way they don't go through everything.