I really doubt you'll have a problem.

Just make sure if all else fails you can squish your purse/laptop into your roll-bag.

I have a habit of buying touristy souveniers on stopovers or at the airside and sometimes even before the airside. I end up with an extra bag all the time from it. I also recently had to unload my laptop, wii, jacket, fuzzy neck pillow, shoes, and if i had it my clear baggy. TSA has no bloody clue who all that stuff belongs to.

I sent a paper bag with a birdhouse, as well as my laptop, laptop case, my shoes, my fuzzy neck pillow and jacket, and my giant roll-on through once too.

I've only ever been stopped for leaving my laptop on in standby mode.

Oh - my giant bag - I actually had issues getting it in the bin on Delta. Never had that happen before, but I had expanded it to squish my wii box into it and then closed the expansion (that's the difference between legal and not on that bag) which apparently didn't compress it quite as much..

Anywho, after looking stupid for a min it squished and fit. No one said a word as i sat down with my fuzzy neck pillow, stowed my laptop under the seat, and got all comfy.