Using Western Union, you can send money from the USA to Cuba. You can only use this service from the USA. You cannot use Western Union in Canada or any other country to send money to Cuba.
The way to send the money is that you initiate the money transfer from the USA to Cuba. You or a friend can walk into any WU branch in the USA and do this. On the Cuban side, you have to find a Cuban citizen who will accept the money for you. This is easy to find. Outside of any WU branch in Cuba you will find people who will accept the money for you. You can pay them 5cuc for this service. Or you just ask your Cuban landlord to help you with this. The Cuban has to sign a paper at the WU office stating that he is not a communist. The transfer then goes through, without a hitch.
You don’t need to do anything else. You don’t need a certificate from the Treasury or anything (As some websites say.)
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