Well, sure, but I sort of assumed Leaf would prevent inference like that by interspersing random feinted baits. Rule #1 of The Game is to ensure that any action you take is very nearly indistinguishable from the actions you would have taken otherwise plus random noise.
The update explicitly said they leaked the information to known compromised operatives. Leaking many falsehoods to them would out that you know who they are. What they did was make sure the truth became known to those operatives. Random feints would have to be known to everyone and you'd have to act as if they were true for the technique to have any value other than telling the enemy that you are onto their shenanigans.
At that point the whole thing just becomes a waste of time and effort. The better strategy, the one people actually use, is to isolate the known compromised operatives in unimportant roles that don't get truly sensitive information. Then you can give them something true as bait, while making sure they never hear about the trap.
Given all of this, the leak could have been:
- Someone in Leaf who knew about the whole plan.
- Someone in Leaf who knew about the bait, and guessed that Mist would see the opportunity.
- Someone in Leaf who knew about the bait, and guessed the existence of a trap.
- The known compromised operatives.
- Anyone in the chain of communications between the compromised operatives and Mist (Remember, these folks don't have actual crypto, just shitty cyphers that an undergrad with a PC could break in a week. Even without a PC they are eminently breakable. Hence the cycling of ciphers at regular intervals.)
- The handlers in Mist who talk to their operatives.
- Others in Mist who knew about the bait and decided to try to grab Naruto.
- Others in Mist who know about the bait, inferred the existence of a trap, and decided to grab Naruto regardless.
- Anyone else who the compromised operatives were selling information to. (I mean, if you have no loyalty to mist, why not also sell the info to any other nation willing to pay?)
And even this is a woefully incomplete list.
Edit: Mind, Leaf is probably still compromised.
That it's by Akatsuki however is less obvious. If they're like canon, they're a small number of very powerful ninja. Sharingan bullshit probably helps you develop an information network more easily, but without an actual coherent organization to back such a network they're still going to finding keeping up with an actual nation in humint very hard.
Not to mention the more developed any such network is, they more likely they are to be found. And a lot of Akatsuki's power comes from their obscurity. Nobody is planning for them if nobody knows about them.
Edit 2: What they probably have is Itachi doing the rounds on some information brokers, grabbing what they know, and then wiping those memories. That has a much lower risk of revealing Akatsuki, and gets them much of the information a good spy network would get, at the cost being unable to choose what information is gathered.
If you're trying to compromise a social graph, fuck with the most well connected nodes. This is why popular people get free clothes.
Edit 3: I didn't notice that Akatsuki came w/ chuunin, so there's a decent chance there is a more coherent organization backing them. Or Itachi brainwashed all of them.