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The Hardest SAT Reading Questions Ever

Posted by Samantha Lindsay | Jul 5, 2015 8:30:00 AM

SAT Reading



If you're aiming for a really high SAT score, you'll need to learn how to beat the most difficult questions on every section of the test. Here, I’ll go through a few of the most difficult questions I’ve seen on the SAT Critical Reading section and how to solve them.

Why exactly are they so hard? How do you tackle them? How well will you do? Challenge yourself for that top score.

Question Type 1: Sentence Completion

Sentence completion questions are tough because you can’t always rely on context to answer the question if you don’t know the word. The hardest sentence completion questions include difficult vocabulary in both the sentence itself and the answer choices, so you’re stuck in a Catch-22. If you can’t be sure what the sentence is asking for, you’re going to have a rough time choosing the right word or even guessing it.

Here’s a single blank sentence completion question that I think is one of the hardest on the publicly available SAT practice tests:

Fred often used ___________ to achieve his professional goals, even though such artful subterfuge alienated his colleagues.

A. chicanery
B. diligence
C. bombast
D. disputation
E. consensus 

This question includes difficult vocabulary in both the sentence (artful, subterfuge, alienated) and the choices (almost all of them). You can understand from the sentence that the word you’re looking for is a synonym for “artful subterfuge”, but what does THAT mean? And even if you do know what it means, the words in the answer choices are also pretty high-level; you might know what diligence and consensus mean, but the other three words are more difficult.

So how would you solve this question?

First, let’s see what we can get from the sentence. Even if you don’t know what “artful subterfuge” means, it must be something negative because it “alienated his colleagues”. If you don't know what "alienated" means, you might be able to infer it from breaking down the word: "alienated" has the word "alien" in it, so it looks like it means "to make alien," which is probably not a good thing.

You’re looking for an answer choice with a negative connotation. This Fred guy is clearly bad news. You can also infer that “artful” means something like “crafty”, or in this case (with the negative connotation), “underhanded”. You need a word that means a dishonest method of achieving goals.

Ok, now we will look at the answer choices. Diligence and consensus are both words you probably know, and neither of them is negative, so you can cross those out.

This is where it gets really difficult - the three choices that are left are words you might not know.

Disputation sounds like a dispute. That’s pretty negative, but it doesn’t really have anything to do with being tricky or underhanded.

Bombast sounds like something that would be loud or big, not artful or tricky, but you might not be sure.

Chicanery could be right. It has the same ending as “trickery”, and it sounds lighter than bombast (in that the word "bomb" is not in it).

It seems like we can narrow it down to bombast or chicanery. Chicanery appeared more likely, so A is the answer we’re going to choose (and the right answer!).

This question might seem impossible on the test if you don’t know the words, but if you make some smart inferences about the sentence and the meanings of the answer choices, you still have a good shot of answering correctly without knowing any exact definitions.

It's not a sure thing (our assumptions about chicanery above were pretty flimsy even if they turned out to be right) (which they did), but you always have a good chance on these questions if you can narrow your answer down to a couple of likely choices.


Now let’s look at a really hard double blank sentence completion question:

Favoring economy of expression in writing, the professor urged students toward a _____ rather than an ______ prose style.

A. spare...ornate
B. terse...opinionated
C. personal...academic
D. baroque...embellished
E. repetitive...intricate

This isn't as difficult in the vocabulary department, but it has confusing answer choices and sentence phrasing that requires a high-level understanding of expressions.

How do we solve this question?

We know from the phrase “rather than” that the two words we use to fill in the blanks must be opposites - that’s important! The professor favors “economy of expression”, so the first word is going to reflect this type of writing style, while the second will be its opposite.

What does “economy of expression” mean? We can infer from what we know about “economy” that it probably means something like not being wasteful with words. So the first word should describe an efficient writing style and the second word should describe a more flowery one.

Now for the answer choices - I think this is the really hard part of this particular question. You have to remember that both words MUST FIT EXACTLY.

First, let’s look at all the first words in the answer choices and see which ones match up with our determination of what the first word must describe. Spare does, terse pretty much does, hmm not sure about baroque, keep that one for now. Personal and repetitive are definitely wrong, so we can cross out choices C and E. It doesn't matter what the second word is if we know the first one is wrong.

Let's move on to the second words in choices A, B, and D.

A. spare...ornate
B. terse...opinionated
C. personal...academic
D. baroque...embellished
E. repetitive...intricate

Spare and ornate are opposites, so A seems to work pretty well. Terse and opinionated don’t work together, because opinionated is definitely not the opposite of terse, so we can cross out choice B. Baroque and embellished (choice D) is a tough one. Embellished definitely works as the opposite of what the professor wants, but we're still not totally sure what baroque means.

So it’s either A or D. At this point, we know that A seems to work, so we should go with that choice even if we are not sure about D. As it turns out, baroque refers to a style characterized by ornate detail (which it to say, not efficient), so A is in fact the correct answer!

With this question, we can see how important it is to verify that both parts of a two part answer fit the sentence. Even with very difficult double blank sentence completion questions, if you break down the answers carefully you can arrive at the correct choice.

Baroque art: proof that people had way too much free time before the advent of modern technology

Question Type 2: Passage-Based

Now let’s look at some of the hardest passage-based reading questions. I’ll break them down by category.

Author Technique

Author technique questions ask about why the author of the passage used a certain emphasis or device in his or her writing. These questions can be very difficult because you need to have a deep understanding of the author’s viewpoint and how different writing techniques work to develop arguments.

Here’s one of the most difficult author technique questions I have seen:

In lines 27-30, the author uses the word "conventional" several times in order to:

A. reveal the performers' frustration with modern theaters
B. disparage the present-day treatment of the arts
C. parody the creative efforts of contemporary artists
D. emphasize the absurdity of a purely aesthetic approach to the arts
E. exaggerate the importance of tradition in the arts

The question refers to these lines in the passage:

The trend toward preservation is significant not only because it is saving and restoring some superior buildings that are testimonials to the creative achievements of other times, but also because it is bucking the conventional wisdom of the conventional power structure that provides the backing for conventional culture centers to house the arts.

I think this question is so difficult because it requires a very specific and nuanced understanding of the author’s goals and technique. It also provides answer choices that are overall pretty confusing.

Let’s figure out how to solve it!

First, we need to understand the question.

Why does the author use the word “conventional” so many times in this paragraph? What’s the viewpoint she is trying to support?

Clearly she is pro-preservation of historic architecture (she describes the buildings that preservation saves as "superior" and "testimonials to the creative achievements of other times", which are both good things), and conventional is being used negatively to describe the systems in place that would dismantle these cultural monuments. She is trying to emphasize how important it is not to allow the “conventional” ideas, systems, and centers to completely take over the arts.

Now let’s look at the answers, remembering to be very picky and specific about eliminating any answers that are even a little bit wrong!

Choice A: reveal the performers’ frustration with modern theaters

True, the phrasing does convey a certain frustration, but is it used to reveal the performers’ frustration? Is it specifically about modern theaters?

Nope. This answer makes itself too specific by mentioning performers and modern theaters, so it’s gotta be wrong.

Choice B: disparage the present-day treatment of the arts

This seems correct. “Conventional” is definitely being used as an insult (to “disparage” something). And it's insulting the attitudes and structures that surround contemporary treatment of the arts in public life.

This one’s a winner!

Choice C: parody the creative efforts of contemporary artists

No, this looks like an irrelevant answer. Contemporary artists are not criticized and certainly not parodied by the repeated use of “conventional”. There’s no mention of contemporary artists at all!

Cross it out!

Choice D: emphasize the absurdity of a purely aesthetic approach to the arts

Hmm...a “purely aesthetic approach” would mean an approach that only takes into account outside appearance. The author does seem like she might reject that sort of approach, but make sure you stick to the question. Is that why she repeatedly used “conventional”?

Pure aesthetics isn’t what she's directly criticizing. It’s more the unfeeling bureaucratic mindset (the "power structure") that pervades today’s decisions about public cultural and artistic matters.

This answer is slightly off from the author’s point, so it’s not going to work!  

Choice E: exaggerate the importance of tradition in the arts

Again, this does seem like something the author would do - she clearly values cultural history - but is it what she’s actually doing here? In this case, “conventional” is used repeatedly to put down the current mindset surrounding the arts, not to raise up the author’s point. It’s part of a negative argument, not a positive one.

This is an example of a weird type of opposite answer.

Choice B is correct!

This question was really hard because it gave a few answer choices that made some sort of sense with regards to the author’s viewpoint but that didn’t directly answer the question. This is why you need to always be sure to keep reminding yourself what you are being asked: to avoid just choosing an idea you saw in the passage but that doesn’t answer the specific question.

If you think it will help, write down a paraphrased wording of what the question is asking that's easier for you to understand so you can stay focused while you look at the different answer choices. 

body_mcdonalds.jpgExample of an American cultural monument, am I right?


Analogy questions are also really tough. They require you to make a comparison between something in the passage and something unrelated to the passage that exemplifies a parallel relationship or theme. This means first understanding an abstract concept in the passage and then matching it to one of five other abstract concepts that sound similar.

Let’s take a look at one of the hardest analogy questions:

The "mystery" discussed in lines 10-13 is most analogous to that encountered in which of the following situations?

A. Being unable to locate the source of materials used to construct an ancient palace
B. Being unable to reconcile archaelogical evidence with mythical descriptions of an ancient city
C. Being unable to explain how ancient peoples constructed imposing monuments using only primitive technology
D. Being unable to understand the religious function of a chamber found inside an ancient temple
E. Being unable to discover any trace of a civilization repeatedly mentioned by ancient authors

Here’s the part of the passage we need to refer to:

But finding Machu Picchu was easier than solving the mystery of its place in the rich and powerful Inca empire. The imposing architecture attested to the skill and audacity of the Incas. But who had lived at this isolated site and for what purpose? 

First, let’s figure out what the question is asking.

Which situation in the answer choices is most similar to the “mystery” described in the passage? So we need to figure out what the mystery is based on the passage.

Going from the first sentence, the mystery is the role Machu Picchu played in the Inca empire. We also should note descriptions of Machu Picchu in the passage to make as direct a comparison as possible. We know it had “imposing architecture” and was “isolated” but no one knows who lived there or why it existed.

Ok, let’s find the most similar answer choice now!

Choice A: Being unable to locate the source of materials used to construct an ancient palace

The mystery in the passage is about the purpose of Machu Picchu in the context of the Incan Empire. It doesn’t involve any confusion about HOW the city was created. This answer doesn’t fit because the mystery has nothing to do with the origin of Machu Picchu, it has to do with its function. 

Get rid of it!

Choice B: Being unable to reconcile archaeological evidence with mythical descriptions of an ancient city

This one doesn't work either. The content doesn't match with the mystery in the passage because there were no mythical descriptions of Machu Picchu. The mystery isn't about any sort of mismatch between the archeological reality of Machu Picchu and how it was described. It's about the fact that its purpose in the Incan empire wasn't described at all. 

Cross this one out!

Choice C: Being unable to explain how ancient peoples constructed imposing monuments using only primitive technology

This one is tricky, because the mystery does involve not being able to explain Machu Picchu’s existence. BUT the mystery is not about the logistics of its construction - it’s about the WHY, while this situation is about the HOW.

This one is also incorrect!

Choice D: Being unable to understand the religious function of a chamber found inside an ancient temple

This answer looks promising - it talks about being unable to explain function, and the mystery is the role of Machu Picchu - synonyms! Explaining the religious function of a chamber found inside a temple is analogous to explaining the function of Machu Picchu in the Incan Empire. How does one part function in the context of the whole it belongs to?

This answer seems correct.

Choice E: Being unable to discover any trace of a civilization repeatedly mentioned by ancient authors

This answer again presents a mismatch between evidence and reality (similar to choice B) when no such conflict exists in the mystery of Machu Picchu - there’s simply no evidence at all.

Another wrong answer!

Choice D is the one we want!

Analogy questions like this require you to think at a pretty high level in terms of inferences because you need to make a connection to something totally outside of the passage.

However, this doesn’t change the rule about looking for direct evidence for your answers. Notice how in this question we focused on the fact that the mystery was about the role of Machu Picchu. By using this evidence, we were able to find the most direct connection in the answer choices by noting that role and function are synonyms.  

body_machupicchu.jpgMachu Picchu - I think I need to go there.


Paired Passages

Paired passage questions contain some of the most difficult questions on the SAT Critical Reading section because they ask you to look at arguments from different viewpoints and make inferences about the views of passage authors.

It's a real mental challenge when these questions ask you to put yourself in someone else's shoes (especially someone whose opinion is different from your own or unfamiliar to you) and then take it one step further and analyze another person's opinion from that viewpoint.

Here’s one of the hardest paired passage questions I’ve seen:

Based on lines 63-67 ("nobody...sheep"), the author of Passage 2 would most likely appear to the author of Passage 1 as

A. a neutral observer of animal behavior 
B. well informed concerning research into animal intelligence 
C. having a deep fondness for border collies and therefore overestimating them
D. having little respect for traditional scientific research
E. having a narrow understanding of what constitutes intelligence 

Here’s Passage 1:


And here are the lines referenced in Passage 2:

“nobody could believe dispassionately in the totality of positive and negative reinforcement after seeing the pure intelligence shining in the face of a border collie intent upon helping a shepherd herd sheep”

How should we go about solving this question?

This is the type of SAT Critical Reading question where it actually is important to read and absorb the whole passage. We need to have a strong idea of how the author of Passage 1 feels about canine intelligence.

From reading the passage, it’s clear that the author of Passage 1 takes a more cynical view of the issue. People are inclined to believe that dogs are intelligent because we are always around them and they are good companions, but this has no basis in scientific fact. What does this mean about the author of Passage 1’s opinions on the author of Passage 2 based on the quote?

Well, it seems like he or she would probably think the author of Passage 2 was naive and falling into the trap of wishful thinking. The quote cites unscientific, emotional evidence of the intelligence of a particular dog breed.

Ok, now let’s look at our choices!

Choice A: a neutral observer of animal behavior

Hmm no, I don’t think so.

This is almost an opposite answer. Clearly the author of Passage 2 is biased towards believing dogs are intelligent. There's no way the author of Passage 1 would think of her as a neutral observer based on her statement about border collies.

Cross it out!

Choice B: well informed concerning research into animal intelligence

Nothing in the quote says anything about research, so it wouldn’t make sense for the author of Passage 1 to consider the author of Passage 2 well informed about animal intelligence research based on the excerpt. 

This is definitely an irrelevant answer - get rid of it!

Choice C: having a deep fondness for border collies and therefore overestimating them

Hmm, this seems possible.

The author's point in Passage 1 was that people’s emotional attachment to dogs causes them to overestimate their intelligence. In Passage 2, the author is clearly citing her own positively biased observations of border collies as evidence of their intelligence. The author of Passage 1 would definitely think she was overestimating border collies because of how much she likes them.

This answer makes sense.

Choice D: having little respect for traditional scientific research

This one isn't going to work - it makes too many assumptions. The quote doesn’t indicate anything about the author of Passage 2’s feelings towards scientific research. There’s no reason the author of Passage 1 would make this specific judgment based on the excerpt.

This is a pretty tricky answer choice. It would make some degree of sense for the author of Passage 1 to believe this about the author of Passage 2 since she's citing anecdotal evidence rather than scientific facts to back up her point about border collies.

However, this answer is too nonspecific to be correct. There's nothing that directly points to the fact that the author of Passage 2 doesn't respect traditional scientific research. She certainly does respect her own (perhaps biased) judgments that aren't based in science, but that doesn't mean that she looks down on real scientific research. 

Eliminate it!

Choice E: having a narrow understanding of what constitutes intelligence

If anything, the author of Passage 2 adopts a wider understanding of animal intelligence than the author of Passage 1 because she entertains the notion that dogs are more intelligent than scientists believe. There’s no reason why the excerpt would cause the author of Passage 1 to believe the author of Passage 2 had a narrow understanding of intelligence.

This one’s wrong too!

Choice C is correct!

I thought this question was particularly tricky because it asked you to do some high-level inference work and provided a correct answer that might at first have seemed too specific. It also gave some other answer choices that appeared plausible but didn't fit with any evidence in the quote from Passage 2.

In these types of questions, it’s important not to doubt yourself and to use process of elimination very strictly. Even if you're being asked to infer something about one passage author from the point of view of another, your inference will still be based on direct evidence from the passages. 

body_bordercollies.jpgIn related news, border collies are too cute to handle.


The most difficult sentence completion questions on SAT Critical Reading will expect you to understand high-level vocabulary in both the sentence itself and the answer choices.

Even if you don’t know specific definitions of all the words, process of elimination can help you get down to one or two answer choices. Remember to look for connotation in the sentence and note relationships between words and phrases so you know exactly what you’re looking for.

The most difficult passage-based questions on SAT Critical Reading will ask you to understand and compare abstract concepts and points of view. 

It's important to always be clear on what the question is asking first. Some choices might be relevant to information in the passage without being a direct answer to the question.

Above all, BE PICKY. The hardest questions are relying on your inability to eliminate slightly incorrect answers. If you can’t find direct evidence for a choice, you have to get rid of it.

Even the hardest Critical Reading questions can be answered confidently with enough practice!


What's Next?

Want more tips on how to master the SAT Critical Reading section? Check out our article on how to get an 800! 

Also, take a look at these articles for more tips if you're still struggling with running out or time or reading the passages on for Critical Reading. 

Finally, here are six strategies you can use to improve your score. Take a practice test to get started!


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Samantha Lindsay
About the Author

Samantha is a blog content writer for PrepScholar. Her goal is to help students adopt a less stressful view of standardized testing and other academic challenges through her articles. Samantha is also passionate about art and graduated with honors from Dartmouth College as a Studio Art major in 2014. In high school, she earned a 2400 on the SAT, 5's on all seven of her AP tests, and was named a National Merit Scholar.

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