Ah! This is a good idea. Put Airboss over telescoping handles of rolling briefcase. Secure the Airboss twice. Once by slipping it's carry handles over the telescoping handles. This will secure the top part. And once by actually using the shoulder strap like a belt around the body of the Airboss and the telescoping handles.

Advantage: This will hold the bag in place quite safely. And you won't need to buy any extra bungee cords or whatever.

Disadvantage: This may possibly take longer do set up and undo. At every security check point you have to separate the contraption.

I again would like to ask why you need an Airboss if you already have a briefcase. OK, I know you carry 2 laptops and probably quite a bit of office stuff. But the Airboss is really one of the bags with the biggest net capacity out there. It is meant and conceived for onebagging. Having this much capacity only for clothes seems like a lot for an ordinary business trip. I could easily pack clothes for more than 14 days in an Airboss.

So chances are that you may actually be able to do with a somewhat smaller bag if you learn how to pack really well. I say this because oftentimes the people who adamantly ask for the biggest carry-on capacity are real space hogs and don't know how and what to pack.

Also keep in mind that an Airboss filled with clothes and shoes to be actually full can already be quite heavy.

Till