I'll be flying back to school in early January, and will be flying back with three laptops, one of which will be in a sleeve (probably non-TSA approved) along with an iPad. I was curious what I will have to do/say in a situation like this, in order to minimize time, prevention of theft, and so my bag doesn't go to secondary.

I am Pre-Check if that makes any difference. I've traveled only so far with one laptop. I will also have other things in my bag like cords.

Take a look at this thread in the Trusted Travelers forum:

Thanks, that was helpful!

On trips that are part personal part work I'll often bring my work laptop (12" macbook) and my personal one (15" mbp). For a while I'd also need a work iPad so I'd have two laptops, two iPads, kindle, phone, spare phone, etc.

Only thing that's wrong with it is my back hurts carrying it and in non-TSA-pre airports it's a lot of stuff to take in and out of the bag.

Here's a tip for avoiding losing/forgetting your laptop and other stuff. Always put your shoes in your last tray that goes on the belt.

Put one laptop in your rollaboard and the other one in your briefcase (or send it through separately). Some x-ray screeners will pull aside your bag in the PreCheck line if there is more than one laptop inside. Yes, I know the rules technically say to keep "everything inside the bag," but I've been told in the past that if there is "too much clutter of electronics," the bag will be held for a secondary inspection, even in PreCheck lines.

The only time I had an issue with two laptops in one bag at pre was when they were nearly identical laptops (Macbook Pro retinas, one minor rev apart), oriented the same in the laptop pocket, and apparently very well aligned. It confused a screener at BOS, who finally asked "Do you have two identical laptops?". Since then I deliberately orient them differently when I go through pre.

It depends on the screening location. You can clear TSA with three laptops, two ten ounce bottles of water, and a bottle opener without question in the precheck lane accidentally. (Whoops). Or you can have them pull out a single surface pro 3 because it "looks like a laptop on the X-ray".

I'm a gadgethead, but I generally tell the TSO that I have "more than one laptop" and then divest any laptops over one to a separate screening bin per laptop. This almost always avoids secondary.

Some TSOs don't care about multiple laptops in the same bag while others will then pick apart the entire bag because "the x-ray was unclear". When they insist that I don't have to divest despite multiple laptops, it's about 50/50. Most TSOs are willing to give you a bin if you ask.