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Well, first:

When you send money using WU/moneygram/ the Jpay/whatever you know for sure they get the money. Whether or not the prisoner gets an actual notice telling them who sent the money—that seems to vary. But regardless, your friend will know they have money when they check their balance.

As for “commissary not being the best route to go”, well, there IS no other route. You cannot send money or books or gifts or, at this point, even letters, postcards, or photos directly to prisoners. You send all of these things through third party companies (amazon, western union, shutterfly, there are even companies you can pay to send handwritten letters FOR you).

When I have asked my friends they say they want books more than money. However, I usually find they need both but won’t ask for money directly. So personally, I set a budget of how much I am willing and able to send my friends. Then I divide that in half and send half books and half money. Your friend may have family that supports them, and you may find they prefer books. Or maybe they don’t like to read but want to look at photos to escape. So maybe they want a magazine subscription.

Each person has different preferences and desires. The way to support people best is to ask what they need and want and then try to give them that.

But when it comes to getting prisoners money specifically, there is only one choice: commissary.