Assuming the player was hoping for a check.
If the player was hoping to get by without a check, however, and no check comes it'd be a very rare player indeed who raised an issue about it. Instead, most players IME would think "Hm - I got away with that one! Lucky me!" and very carefully say no more about it. To me the Lady Askar(?) example looks like one of these.
In broader terms beyond just this example: just because a player benefits from a GM error doesn't make it any less of an error.
See, to me, this post and the one before it, in which you talked about players "getting away with stuff" and that "they always go along with what they want", etc. smacks of an ethos in which the GM is some sort of task master/enforcer. That the players are these little miscreants who just want to have treasure handed to them, and it is the job of the tough guy GM to make it hard for them.
IMHO this is a way, simplistic perhaps, to interpret Gygaxian skilled play, but it is anathema to, certainly diametrically opposed to, the type of gameplay we are talking about. There are not two sides in these narrative construct/fiction first games! DW's GM agenda literally instructs the GM to be a fan of the PCs and an advocate for the players. They aren't some sort of 'opposed teams'! There is no such thing as players "getting away with it." This is what I would call antiquated thinking, at best. All the participants at the table are generating a fiction (play to see what happens) and all of them have the same goal, interesting and engaging fiction. Because it is an RPG that is going to focus on character and how it interplays with setting, genre, etc. through dramatic conflict. It also has elements of exploration and the other foci that you will see called out by WotC people when they talk about different kinds of players.
Even in Gygaxian skilled play I would say that a similar ethos is actually in play. The GM never simply pitches the PCs into hopeless situations. There aren't Invisible Stalkers on level 1 in the front corridor that slay everyone who enters, or pit traps filled with lava that do 100 points of damage with no save or chance to detect them. Remember, this was actually called out in the original Tomb of Horrors. The intro to the module literally says "This is unsurvivable, every PC who enters this dungeon will die. Go to the back of the book and run the pregens! Don't use any PC you care about." Given the sheer volume of ways PC spell casters can attack a problem some people DID get to the end of the module, but IME it is pretty rare! Clearly 'normal dungeons' are built so that the PCs are very likely to advance and surive IF THE PLAYER IS GOOD AT PLAYING D&D. The goal is not any sort of verisimilitude or reasonable and believable anything. It is to have a kick ass time beating the, hard but beatable, dungeon.
This is what informs my thesis about how play is really driven. You might have a model of GM vs Player at a superficial level, but at most your trying to make a 'fair test'. What we're doing is a bit different, but the ultimate goal is basically the same, to have a fun tale emerge at the end of the night. Yours might emphasize player puzzle-solving, loosely, and GM as puzzle-giver, and ours emphasizes GM as 'plot complication giver' and involve a more overtly cooperative model of how that works, but we are all ACTUALLY on the same side.
I just find it a lot easier to explicitly think that way, because bringing our thought processes and interests out into the open and putting them on the table is generally a more successful way to get to success reliably.
I mean, there's no reliable numbers on any of this I'm sure, but I am of the opinion that it is much more likely for a game run in a style like, say,
@Manbearcat's to 'hit the mark' than it is for one where some people pick up D&D and try to run it in a classic fashion. That if you went across all the groups that did the latter, most of them achieved limited, or no, success. Most of the groups which tried the former OTOH, I suspect a lot of them succeeded. I think the 'classic D&D way' is just vastly more obvious. It doesn't take much analysis or explaining to get going with. It is successful enough of the time that if you try a few times you'll probably achieve enough satisfaction to keep playing. The other way is unlikely to just come about when random naive people try to play an RPG. Yet if you teach it to people it really does click well.