DSAT-8.4

Plurals, Possessives & Frequently Confused Words

Master its/it's, their/there/they're, whose/who's, and apostrophe placement for singular vs. plural possessives on the Digital SAT Writing section.

What you'll do in this lesson

A voice-first session with the Crimsora tutor on Plurals, Possessives & Frequently Confused Words, then targeted practice and FRQs — with the tutor adapting to where you get stuck.

What this lesson covers

On the Digital SAT, a handful of tiny words trip up strong readers all the time. The test loves swapping itsit's for itsits or asking whether an apostrophe belongs before or after the ss. These questions look like grammar trivia, but they follow strict, learnable rules — and once you know the rules, they become fast, reliable points.

This lesson focuses on two closely related skills: choosing the correct member of a frequently confused word set, and placing apostrophes correctly to show possession versus a simple plural. You will learn the substitution tricks that expose the right answer in seconds, plus the common traps the test writers rely on.

Contractions vs. Possessives: The Apostrophe Test

The single most tested confusion is between a contraction (two words squeezed together with an apostrophe) and a possessive pronoun (which never uses an apostrophe). The trap works because both sound identical.

Here is the master move: whenever you see one of these words, expand the apostrophe version into its full two words and check whether the sentence still makes sense.
WordTypeExpands toTest sentence
itsit'scontractionit is / it has"It is raining"
itsitspossessive(belongs to it)"the dog wagged its tail"
they'recontractionthey are"They are late"
theirpossessive(belongs to them)"their house"
therelocation/existence"over there"
who'scontractionwho is / who has"Who is there?"
whosepossessive(belongs to whom)"whose book"
If "it is" or "it has" fits, choose itsit's. If it does not fit, you need the possessive itsits. The same logic applies to who's versus whose and they're versus their.

A key misconception: students assume that possession always needs an apostrophe. That is true for nouns (Maria's car) but never for possessive pronouns. Its, theirs, whose, yours, and oursours are already possessive and take no apostrophe.

Their, There, They're: A Three-Way Split

This trio adds a location word to the contraction-versus-possessive pair, so you need three quick checks.

Use they're only when "they are" fits. Use their when something belongs to a group — it will be followed by a noun (their backpacks, their decision). Use there for a place or to introduce existence, as in "There are three reasons" or "Put it over there."

A fast decision order works well on test day. First, try substituting "they are." If it fits, the answer is they're. If not, ask whether the word is followed by a noun that it owns; if so, choose their. Otherwise, the answer is there.
SentenceCorrect wordWhy
"___ going to be late."they're"they are going" fits
"I like ___ new logo."theirlogo belongs to them
"Leave the boxes ___."thereindicates a place
"___ are two options."thereintroduces existence
The Digital SAT rarely asks you to define these words; instead it embeds one in a sentence and offers all three as choices. Because the surrounding sentence supplies the meaning, the substitution test almost always isolates a single correct answer.

Singular vs. Plural Possessives: Apostrophe Placement

When a noun owns something, an apostrophe shows possession — but its position tells the reader how many owners there are. This is the other half of topic 8.4, and the Digital SAT tests it constantly.

The rule has three steps. First, identify the owner word before adding any apostrophe. Second, decide whether that owner is singular or plural. Third, apply the placement rule.
MeaningFormExample
One student's itemadd s'sthe student's locker
Many students' itemadd ' after the ssthe students' lockers
Plural, no ownershipno apostrophethe students arrived
Irregular plural owneradd s'sthe children's toys
So student's means one student, while students' means two or more. For irregular plurals that do not end in ss (children, women, men), you still add s's: children's, women's.

The most common trap is offering a plain plural where a possessive is needed, or vice versa. If the noun is simply naming more than one thing and owns nothing, it takes no apostrophe at all. Read the noun that follows: if the word after is a thing being possessed, you need an apostrophe.

How the Digital SAT Frames These Questions

These items appear in the Standard English Conventions portion of the Reading and Writing section. The question stem is almost always the same generic prompt: "Which choice completes the text so that it conforms to the conventions of Standard English?" That means the exam will not tell you the topic — you must recognize it from the answer choices.

A huge clue: when the four choices are the same word spelled different ways, such as itsits / itsit's / itsits' / it is, you know you are looking at a confused-word or apostrophe question. (Note that itsits' is never a real word, so you can eliminate it instantly.)

Your workflow should be efficient. Scan the choices to identify the confusion type, run the substitution test for contractions, count owners for possessives, and eliminate any nonstandard spellings. The correct answer will be exactly one option.

Because the passages are short and self-contained, you rarely need context beyond the single sentence. Do not overthink meaning; these are mechanical rules. Speed here banks time for harder rhetoric and evidence questions elsewhere in the module.

Key terms

Contraction.
Two words combined with an apostrophe replacing missing letters, such as itsit's for "it is" or who's for "who is."
Possessive pronoun.
A pronoun showing ownership that never uses an apostrophe: itsits, their, whose, yours, oursours, theirs.
Singular possessive noun.
A noun with s's added to show that one owner possesses something, as in the student's grade.
Plural possessive noun.
A plural noun ending in ss with an apostrophe added after the ss to show multiple owners, as in the students' grades.
Irregular plural.
A plural that does not end in ss (children, women, men); it forms the possessive by adding s's.
Substitution test.
Expanding an apostrophe word into its full form (it is, they are, who is) to check whether a contraction is correct.
Standard English Conventions.
The Digital SAT question category covering grammar, punctuation, and usage rules like these.

Worked example

The research team announced that ___ findings would reshape the field, though ___ still unclear how quickly other labs will adopt the new method.

Choices for the first blank: (A) their (B) they're (C) there (D) theyre. Choices for the second blank: (A) its (B) it's (C) its' (D) there.
Start with the first blank. Try the substitution "they are": "they are findings" is nonsense, so eliminate they're (choice B). The word theyre has no apostrophe and is not a real word, so eliminate D. Between their and there, ask whether the word owns the noun that follows. The findings belong to the team, so you need the possessive their. The answer to the first blank is their.

Now the second blank. The sentence reads "___ still unclear how quickly." Try "it is": "it is still unclear how quickly" fits perfectly, so a contraction is required. That points to itsit's. Confirm the others fail: itsits is possessive and would need a noun to own, which is not present; itsits' is never a valid spelling; there does not fit the meaning. The answer to the second blank is itsit's.

The combined correct sentence: "The research team announced that their findings would reshape the field, though it's still unclear how quickly other labs will adopt the new method."

Practice questions

Which choice completes the text so that it conforms to the conventions of Standard English?

After the storm passed, the volunteers repaired the ___ damaged roofs one house at a time.
  1. neighbors
  2. neighbor's
  3. neighbors'
  4. neighbors's

Answer: neighbors'

Multiple neighbors each own a roof, so you need a plural possessive. A plural ending in ss takes an apostrophe after the ss: neighbors'. The plain plural neighbors shows no ownership, neighbor's would mean only one neighbor, and neighbors's is not a standard form.
Which choice completes the text so that it conforms to the conventions of Standard English?

The committee has not yet decided ___ proposal will receive funding this year.
  1. who's
  2. whose
  3. whos
  4. who is

Answer: whose

Run the substitution test: "who is proposal" makes no sense, so the contraction who's is wrong, and "who is" fails for the same reason. The blank shows that the proposal belongs to someone, so the possessive whose is correct. WhosWhos is not a word.
Explain why "its" is correct in the sentence: "The company revised its privacy policy after the audit." What would have to change for "it's" to be correct instead?

Answer: "Its" is the possessive pronoun showing that the privacy policy belongs to the company; no apostrophe is used because possessive pronouns never take one.

Test the alternative: substitute "it is" to get "the company revised it is privacy policy," which is ungrammatical, confirming the contraction is wrong here. For itsit's to be correct, the sentence would need to use "it is" or "it has" logically, for example "It's clear the policy needed revision," where "It is clear" fits.

FAQ

Is "its'" ever correct?
No. ItsIts' is never a valid English word. The only two options are itsits (possessive) and itsit's (the contraction for "it is" or "it has"). If you see itsits' among the choices, eliminate it immediately.
How do I quickly tell a plural from a possessive?
Ask whether the noun owns something. If a noun is simply naming more than one thing and nothing belongs to it, use a plain plural with no apostrophe. If the noun is followed by a thing it possesses, add an apostrophe: s's for one owner, ' after the ss for multiple owners.
Does the Digital SAT tell me which grammar rule a question is testing?
No. The prompt is a generic "conforms to the conventions of Standard English" question. You identify the rule from the answer choices. When the four choices are the same word spelled differently, you are looking at a confused-word or apostrophe question.
What is the fastest way to choose between their, there, and they're?
First substitute "they are"; if it fits, pick they're. If not, check whether the word is followed by a noun it owns, which signals their. If neither applies, the answer is there, used for a place or to introduce existence.

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