Editors spend a lot of time making decisions related to hyphens. That’s because hyphenation depends not only on accepted usage but also on context—and sometimes on both.

For example, many terms that are hyphenated as adjectives before a noun are not hyphenated when they follow the noun. A well-edited document would be described as well edited, and a long-term plan would play out in the long term.

Other terms won’t depend on context. When we work on-site or online or on-screen, our on-site and online and on-screen activities might be set aside whenever we decide to go off-line. These terms are generally invariable—unless you prefer onscreen and offline. Dictionaries don’t necessarily agree, and spelling and grammar checkers tend to ignore such variations.

So how can proofreading software help you sort it all out?

PerfectIt’s Hyphenation Check

PerfectIt is a proofreading add-in for Microsoft Word that scans your documents for inconsistencies and other potential problems in several categories, including hyphenation, spelling, capitalization, italics, abbreviations, numbers, and lists. As with Word’s spelling and grammar checker, PerfectIt gives you a chance to review each item one by one and decide what to fix and what to skip.

For example, if PerfectIt finds “well-edited” in five places and “well edited” in three, it will list all eight and show you the surrounding context for each. However, it won’t know which of them, if any, need fixing. That’s where your editorial judgment comes in: Does the term modify and precede a noun? Then it should have a hyphen. If not, no hyphen.

If, on the other hand, PerfectIt finds both “on-site” and “onsite” (one word), you could choose “on-site” as your preferred spelling and go through PerfectIt’s list to add a hyphen to fix each instance of “onsite.” Ditto for “on-site” versus “on site” (two words). But context matters here too. Make sure, for example, that you don’t add a hyphen to something like this: “The research focused on site management.”

Keep in mind also that your preferences aren’t the only ones that matter. For example, you would generally want to preserve “onsite” or “on site” if either occurs in a direct quotation or in the title of a work—assuming it has been transcribed correctly from the original source.

As with spelling and grammar checkers, the final decision in each case is yours.

But back to onsite v. on-site v. on site: How do you know which one of the three is Chicago style?

The Chicago Manual of Style for PerfectIt

For matters of spelling, including hyphenation, Chicago usually defers to the first-listed entries in Merriam-Webster. For terms not found there, the recommendations in The Chicago Manual of Style, starting with the hyphenation guide at CMOS 7.89, take precedence.

Many of these preferences have been built into Chicago Style for PerfectIt, saving you the time of looking them up. For example, Chicago Style for PerfectIt will find any instances of “onsite,” “on-line,” “onscreen,” and “offline” and suggest the preferred forms:

If you need more guidance, clicking on “See more from CMOS 7.89” will display an excerpt from the hyphenation guide in CMOS:

If you need more than that, the red numbers link directly to the corresponding sections in CMOS Online.

Sometimes, however, your preferences will conflict with Chicago’s. Maybe your publisher’s house style departs from Merriam-Webster for certain terms, or maybe you’re editing a book that has a specialized vocabulary. Then you’ll want to use PerfectIt to create a new style based on Chicago but edited to reflect your preferences and to add terms not included in Chicago Style for PerfectIt.

Defaulting to Consistency

Terms like well-edited, on the other hand, have not been added to Chicago Style for PerfectIt. For starters, well‑edited isn’t in Merriam-Webster. But even if it were—like the similar adjectives well-read and well-known—hyphenation would still depend on context. Chicago and other styles usually take precedence over Merriam-Webster, leaving phrasal adjectives open when they follow a noun.

For those terms, PerfectIt’s regular consistency checks still apply. This means, however, that PerfectIt may miss a term like well-edited that’s been consistently (but incorrectly) hyphenated both before and after a noun. That’s why it’s important to do a careful copyedit also.

When PerfectIt does find an inconsistency, you’ll still have the option of getting more specific details from CMOS. In the case of “well-edited,” the advice has been adapted from CMOS 7.85:

Anticipating Exceptions

If you’ve paid attention to Word’s grammar check, you know that software alone can’t anticipate every possible exception to a rule. The same is true for PerfectIt. We noted one of these exceptions earlier, in the example “research focused on site management”; in that context, “on site” would show up as a false positive in a consistency check that also finds “on-site” in the same document.

Another example: PerfectIt might find “daughter in law” in one place and “daughter-in-law” in another. The hyphenated version is correct—except in something like “a daughter in law school” or “a daughter in law enforcement.” And there’s a difference between “twenty-first birthday” and “twenty first-floor apartments” or “twenty first graders.”

Another one: In Chicago style, the phrase “half-finished” is hyphenated as an adjective both before and after a noun. But what about “among the thirty students who showed up, only half finished the test”? That’s another potential false positive.

Editors know to spot such exceptions and ignore them. But Chicago Style for PerfectIt tries to help in limited cases. For example, it will look for the unhyphenated version of every ordinal from “twenty-first” through “ninety-ninth” and suggest a hyphen. However, it’s been programmed to ignore any one of these terms when it occurs immediately before a hyphen or the word “graders.”

Others are more difficult to control for. Chicago Style for PerfectIt will spot “is/are/was/were half finished,” where “half-finished,” with a hyphen, would almost always be correct. But it will ignore any other instance of “half finished” except as part of the consistency check. Still, when PerfectIt does flag one of those four set phrases, you’ll be reminded of the principle:

That’s one of the main values of Chicago Style for PerfectIt. With its advice and direct links to CMOS, it can help you learn the style while double-checking your documents.

An Easier Way to Master Chicago-Style Hyphenation

It can take time for editors to learn Chicago-style hyphenation. Even experienced editors won’t be perfectly consistent, and all editors need to look things up at least sometimes. The idea behind Chicago Style for PerfectIt is that it teaches the principles.

The trick to learning the principles through PerfectIt is to make use of the built-in guidance from CMOS. These bite-size excerpts offer advice and recommendations directly from the Manual. So when PerfectIt stops on “a-priori arrangements” or “a 50-percent increase” or “Asian-American novelists”—and you’re not quite sure why—take a moment to read the explanation from CMOS. Maybe it will take running ten documents through PerfectIt. Maybe it will take more than that. But before too long you will have mastered Chicago hyphenation style without even picking up the book.

Learn More

By itself, PerfectIt will find where you’ve been inconsistent with your hyphens. But in Chicago Style for PerfectIt, you’ll get the additional benefit of recommendations adapted directly from CMOS. Think of it as your chance to learn something about Chicago’s hyphenation style while perfecting your documents. That, to borrow a hyphenated cliché from the world of business, is a win-win situation.

To learn more about The Chicago Manual of Style for PerfectIt or to apply it on your next document, click for details.

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Photo: Half What?, by Kalyan Chakravarthy, CC BY 2.0 (adapted for post).

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