Anyone can freely book anyone a ticket on any airline I can think of --at least that's always been the case as far as I know--online, at airport, on phone.

Ok for those who do not wish to read more of my thoughts on all of this, stop here and say no more. Otherwise, added friendly and constructive commentary on the information below is welcomed...

Ah, but do not ever let the airline perceive of your activities involving any kind of payment, compensation, profit or barter. It'd be one thing if the CSR you were talking with on the phone at the airline joked with you about how your friend bought you a bottle of fine wine for booking him a ticket, but it's a whole other ball of wax if they begin to assume you are doing something for what they think is monetary gain. Do not even ever want to find out what they think on that stuff! (no it has not happened to me)

And yes, in some cases, the booking of someone else online can involve some minor issues:

-Some airlines require you use your own CC to book the ticket, in which case, your friend now owes you the fees associated with the tickets, if any, and this payment, if ever asked about by an airline, needs to be distinguished from anything involving the booking with the miles themselves. And of course, this is between you and your friend to sort out, but just keep a copy of all ticketing information for yourself in case it ever comes up. In other words, if ever asked, you would say something like, "Yes, I booked him a ticket for 50,000 miles. He paid me the $20 fee that was charged to my card to book this online as shown here..." (produce copy)

-In some cases, people have been asked to produce the CC that was used to book the ticket even when miles were used to do so, and if this happens, it would be at the gate where the ticket holder would have to explain that a friend purchased it with miles and paid fees as directed by the airline.

And while we are on the subject, Some hotels do things very differently depending on hotel chain and status:

I recall SPG only ever letting someone book a room for someone else when the person doing the booking is Platinum. Or was it that they had to be related? I cannot remember but that stuff gets dicey and perhaps others wish to clarify the hotel thing going forward.

One last thing about booking award tickets for others:

I recently booked for a relative to fly from a Western EU country to the States. Well two things went wrong and them having an award ticket did not help:

1) The traveler's hyphenated last name was somehow messed up by the airline's booking system (it was never made clear exactly how, but either they dropped off one part of the name or reversed them--either way, they quickly rectified the situation)

2) Neither I nor the Eu traveler had ANY idea that some countries of even Western Europe have become required to obtain and download some new forms for visiting travelers that must be filled out in order to enter the USA. Had they booked their ticket say, with cash or credit at a local area travel agency, this all would have been done for them on the spot and they may have never really given it a second thought except to bring this or that paper with them when going to the airport. But because I booked it for them using miles from my computer in the States, nothing was done and I really did not have any way of being aware of this paperwork being needed--and nor did the passenger. Why would we? When I travel into the States, I have a US passport so I would never encounter it. Nor would any traveler with say, a residence visa or dual passports.

Because of all of this, all these forms had to be completed on the fly at the airport in EU (cost about 14 euros) and had this all not been completed with the help of a willing airline agent that happened to be available, the traveler would have been sent home. Because it was an award ticket and was booked online from overseas, some at the EU airport viewed it as less able to be worked with and were nearly unwilling to help the traveler get going. As well, not much could be changed with the economy ticket anyway unless that same itinerary were available say, the next day or week or month, and that wasn't going to work. This almost stunk, but everything did work out.

Point is, when booking award travel for others, it is up to us/the traveler to find out everything about the flight even after getting it booked with miles---even when we have no idea what we are looking for.

It is often why, if I book travel using my miles for family or friends, I tell them that what they are getting is a free ticket from me and in return, all I want appreciation for that, and not complaining about the flight or anything surrounding it. That's not my fault. If you act as though it is, then next time, just go pay on your own.