Hyphens, En Dashes, Em Dashes

Q. We are struggling with hyphenating trans-Atlantic and trans-Pacific. AP says to hyphenate; Chicago does not. But you say to hyphenate trans-American. If Atlantic, Pacific, and American are all normally capitalized, shouldn’t they all follow the same hyphenation standard for prefixes?

Q. Please, please help. How does one hyphenate this phrase: “twenty-five-thousand-dollar fine” or “twenty-five thousand-dollar fine”? I am not able to find an example in all of CMOS.

Q. Where does Chicago stand on this “eco” compound word madness? Everything that comes across my desk these days is “eco-conscious, ecobusiness, eco centered,” and of course not a single word of it is consistent.

Q. How should the following be hyphenated, if at all? Two and a half hours.

Q. I tend to let my ear be my guide—and usually that works—so I need some clarification to ensure I’m on the right track. Can you clarify that I am using my hyphens correctly? Facilitate a core-team workshop to discuss . . . Develop a future-state document . . . Conduct a future-state assessment . . . Identify change-management opportunities.

Q. I can’t find hyphen placement in ages, such as “fourteen-years old” in the Manual. And what about “years-old”? Is that correct?

Q. Is “official-rate increases” hyphenated as written?

Q. “We are more than ready to analyze plan design changes.” For clarity would you recommend inserting a hyphen between plan and design?

Q. Is it prework or pre-work (for work that is to be done before a meeting)?

Q. I am copyediting a parent resource website and this comes up a lot. How do I hyphenate “this class is for three- to four-year-olds”? Is that correct? I have seen it as: three-to-four year-olds.