Our prison system is nothing to scoff at. Yes, we still have repeat offenders and you taxpayers still have to dump a lot of money into it, but that does not mean that it isn't well-maintained. Rather, prisons are surprisingly strict institutions which make you shower naked with other men. I know this, because I once served something that people might call "tough time" in the "bird house." I am an ex-con, but I am not here to gloat about it. I concede that my actions were wrong and I will never again call the bluff of the MLB and Upper Deck by creating my own trading cards. Nevertheless, my time in the "puke" was made much better by my friends and family who would try their best to sneak items in from the outland (a term that me and my prison kin used, meaning: the outside.)
Note: I do not advocate the use of items that can potentially break someone out of jail or end lives. If you read this and sneak in some malicious items into the "Big pot," I will personally distance myself from you and contact major broadcasting companies to tell them how stupid you are. I am here to be an assistant to help you, not break the law and cause distress to the fine guards at the "CitiBank of Broken Dreams"
This is an old standby, and largely because it is perfectly practical in everyway. Simply bake whatever item the imprisoned loved one wants into a delicious cake and send it over. Guards never expect this, because they naturally associate cake with good tidings and legality. Also, they do not want to impose in checking or wanding the cake, as it might seem as if they are jealous that the prisoner has it so good!*
*Until the guards throw him a blanket party after lights out. It might seem harsh, but harsh is what "The Moint" is all about, kid.
Items that can be hidden
Harmonica - Is your friend a blues singer? Then this seems natural.
Recorders - Both the audio equipment and the musical instrument.
A file - NOT to make their nails pointy and knife-like, but to make sure they look nice.
This one is limited to conjugal visits, mainly because it is hard to pull of in any other way, and trying it with anyone within your family that isn't your spouse might seem strange and unsettlingly arousing. Simply use the pockets that God gave you in order to sneak items past guards. If this feels uncomfortable at first, then you obviously have not been in prison for that long. My time spent serving at "The Ballpit" for in-fielder's trading has netted me a sphincter the diameter of a croquet ball.
Items that can be hidden
Croquet ball - Elasticity pending, and it makes a nice trophy to show to your friends
Bag of shampoo - Much like food on airlines, prison shampoo is widely regarded by stand-up comedians as the worst out there. Might as well live a little with the good stuff.
Crowbar - Only if it's a comfort item of the prisoner and would improve his quality of life by having it around.
This only implies to prisons that operate in Australia and near the Indian Ocean. Also, prisons who mainly hold inmates that are fish who have committed crimes against other fish. The upside of using a fish to sneak in contraband is that he will blend in with the rest of the fish and won't raise suspicion. Now you might think that you will never use this, but crazier things have happened. Remember that time a guy gave a lottery ticket to his waitress and it ended up being a winner so they both became millionaires? Exactly.
What items can be hidden
Algae - It is more nutrious than people give it credit for.
Fish bones - To use as toothpicks or currency
Chainsaw - For cutting down trees.