Part of speech can change title capitalization for surface-identical words such as “than,” “like,” “over,” “off,” and phrasal particles. A reliable converter therefore needs reviewed grammatical context instead of a single lowercase-word list.
ReviewedEvidence6 sourcesSectionWriting & Style
Quick answer
Yes. In styles such as Chicago, a word can be lowercase when it is a short preposition but capitalized when it is a verb, conjunction, adverb, or phrasal particle. First/last-word rules can override that distinction at title boundaries.
Style ScopeChicago 18 and other grammar-sensitive title styles
Important caveats
Automation boundary
Context patterns never become a general parser. If the reviewed rule set cannot establish the relevant role, the token remains left unresolved rather than being guessed.
Further guidance
Reviewed Examples
“Like” can be a verb or a preposition; “over” can be a preposition or adverb; “till” can be a preposition or conjunction. This guide stores only narrow source-backed context patterns that resolve reviewed examples.
Why Grammar Matters
Chicago’s own Q&A treats words such as “than” differently by grammatical role and advises checking dictionaries when part of speech determines capitalization.
Sources and evidence
Sources are shown with the role they play in this guide. Historical or style-sensitive claims are kept within the evidence boundary described above.
Chicago 18 uses title case for titles of works and changed a long-standing rule: prepositions of five letters or more are now capitalized. Shorter prepositions generally remain lowercase internally, while first and last words are capitalized and “to” remains lowercase as an infinitive marker in ordinary mid-title use.
APA capitalizes “Like” internally because it has four letters. Chicago 18 lowercases it when used as a short preposition but capitalizes principal-word uses such as a verb; MLA likewise depends on grammatical function. This guide keeps style-specific rules separate and marks grammatical ambiguity where the same spelling can play different roles.
APA capitalizes “Near” internally because it has four letters. Chicago 18 lowercases it when it is a short preposition but capitalizes adverb/adjective uses; MLA likewise distinguishes minor-preposition from principal-word uses. This guide keeps style-specific rules separate and marks grammatical ambiguity where the same spelling can play different roles.
“Off” cannot be assigned one safe capitalization from spelling alone. As a short preposition it is normally lowercase internally in APA and Chicago, but as an adverb or verb particle it is a major word and is capitalized; the surrounding phrase determines the answer.
APA capitalizes “Over” internally because it has four letters. Chicago 18 lowercases it when it is a short preposition but capitalizes it when it functions as an adverb; MLA treatment likewise depends on whether it is functioning as a minor preposition or a principal word. This guide keeps style-specific rules separate and marks grammatical ambiguity where the same spelling can play different roles.
“Than” exposes a genuine style-engine edge case. APA capitalizes it because it has four letters, while Chicago 18 may lowercase it as a preposition but capitalize it as a conjunction, so Chicago output can depend on the grammatical structure of the title.
Until and till can both function as prepositions or subordinating conjunctions. APA capitalizes both because each has at least four letters. Chicago 18 capitalizes until, while till needs grammatical-role analysis because a four-letter preposition is lowercased but a subordinating conjunction is capitalized. MLA likewise depends on whether the word is functioning as a preposition or a subordinating conjunction.
Hyphenated compounds cannot be capitalized safely with one universal “capitalize everything after a hyphen” rule. APA explicitly capitalizes the second part of hyphenated major words, while Chicago 18 changed its prefix-compound treatment and still applies grammatical title-case rules to individual elements.
