This achievement requires you to evade capture from the cops 5 times in a single contract.
The earliest you can get this is Story Contract 2 as you're introduced to hiding spots in this contract, but odds are you'll unlock this naturally. The best way to approach this is to first use your Cleaner Sense by pressing
. Doing this will show you the location of all the hiding spots in the level.
Now simply hang close to a hiding spot and either wait for a cop to see you or step into their vision cone. Once their cone goes from orange to red, that means they see you, so quickly get into your hiding place by pressing the
button. They will remain by the hiding place for a bit, and then they will give up looking for you. You'll know when a cop gives up when their vision cone goes from red back to orange and they return to their original patrol route.
Simply repeat this process four more times and the achievement is yours.