Tricky Capitalization Cases, Solved

The basic rules of title case take five minutes to learn. These are the other cases — the ones where careful writers hesitate — worked through one at a time, with the reasoning behind each call.

By the TitleCaseMaker Editorial Team · Last updated: July 26, 2026

Case 1: The word after a colon (and a dash)

Whatever follows a colon in a title is treated as the start of a subtitle, and subtitles begin with a capital letter in every major style: Deep Focus: A Field Guide to Attention. This holds even when the next word is an article or short preposition that would otherwise be lowercase. APA extends the same promotion to the first word after an em dash used to introduce a subtitle. The mistake to avoid is the halfway version — capitalizing after some colons and not others in the same document. The rule has no exceptions, so apply it mechanically.

Note the rule is about subtitles, not every colon in running text. In a sentence-case heading like One warning: read this first, house styles differ — but in title case, capitalize after the colon every time.

Case 2: Hyphenated compounds

Hyphens create the most second-guessing per character of anything in title case. The working rules:

When in doubt, ask whether each element could stand alone as a meaningful word in the title. If yes, capitalize it; if it is glue (to, of, the), leave it lowercase.

Case 3: Short prepositions, long prepositions

Prepositions are the one part of speech the style guides genuinely disagree about, and the split is clean. APA, AP and AMA use a length test: three letters or fewer stays lowercase (of, to, in, on, at, by, up), four or more gets capitalized (With, From, Over, Under, Between, Through). Chicago and MLA lowercase all prepositions regardless of length — with, between, even notwithstanding. So Working With Sources (APA) and Working with Sources (Chicago) are both correct, in their own worlds. There is no universal answer; there is only your chosen guide's answer. The full split, with tables, is in our style guide comparison.

Case 4: Phrasal verbs vs. plain prepositions — the sneakiest case on this page

Compare these two correct titles:

Same two letters, opposite cases. In the first, up is part of the phrasal verb set up — it belongs to the verb, so it is capitalized like a verb. In the second, up to is a plain prepositional phrase, so up stays lowercase. The test: say the sentence without the little word. If the verb collapses or changes meaning (set your studio?), the particle is part of the verb — capitalize it. If the meaning survives (costs 50% less), it is a preposition — follow your style's preposition rule. The same logic gives you Log In Before You Start, Back Up Your Files, and Turn Off Notifications, versus a Cabin in the Woods and News from off the Coast.

Case 5: Proper nouns that break the rules on purpose

Title case never overrides how a proper noun spells itself. Three families to watch:

The principle: proper-noun spelling is a fact about the noun, and facts outrank formatting.

Case 6: The first-word and last-word rules

The two positional rules outrank everything else in title case. The first word and the last word are capitalized no matter what part of speech they are: The Art of the Possible, Something to Believe In, A Cause Worth Fighting For. Writers reliably apply the first-word rule (sentence habit does it for them) and reliably forget the last-word rule, because a trailing for or in feels minor. Positional rules beat part-of-speech rules — that is the hierarchy. And it cascades: in a title with a subtitle, the first word after the colon gets the same promotion (Case 1), and the last word before the colon does in some house styles too — check your guide if your title splits down the middle.

Case 7: A few words that refuse to behave

A 15-second checklist for any tricky title

  1. Run the title through the converter in your chosen style to get the mechanical rules right for free.
  2. Scan for colons — is the word after each one capitalized?
  3. Scan hyphens — is every standalone word in the compound capitalized, every glue word lowercase?
  4. Find the little words next to verbs — phrasal-verb particles up, plain prepositions down.
  5. Restore any proper-noun spellings (iPhone, van Gogh, acronyms).
  6. Check the last word. It is capitalized. It is always capitalized.

If a title survives that list, it will survive an editor. For the errors that show up long before these subtleties matter, start with the ten most common capitalization mistakes.

Frequently asked questions

Is 'up' capitalized in a title?
It depends on its job. Capitalize it when it is part of a phrasal verb ('How to Set Up Your Studio', 'Back Up Your Files'); lowercase it when it is a plain preposition ('up to 50% Less'). Test by removing the word — if the verb's meaning collapses, it is part of the verb.
Do you capitalize both words in a hyphenated title word?
Capitalize both elements when both are real standalone words ('Long-Term', 'Self-Esteem'), but keep minor connecting words lowercase ('Day-to-Day', 'State-of-the-Art').
How do you capitalize iPhone at the start of a title?
Brand spellings beat title case, so 'iPhone' keeps its lowercase i even mid-title. Most editors avoid the conflict at the start of a title by rewording so the brand name is not the first word.
Is the word after a colon capitalized in a title?
Yes, always. APA, Chicago, AP, MLA and AMA all capitalize the first word of a subtitle after a colon, even if it is an article like 'the' or 'a'.

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