Hyphens with the Prefix re
Many of us find hyphens confusing. The prefix re can make hyphenating even more of a head-scratching experience. However, there is really only one rule that you need to learn to determine when to hyphenate with re.
Rule: Use the hyphen with the prefix re only when re means again AND omitting the hyphen would cause confusion with another word.
Example: Will she recover from her illness?
Re does not mean again so no hyphen.
Example: I have re-covered the sofa twice.
Re does mean again AND omitting the hyphen would have caused confusion with another word so hyphenate.
Example: The stamps have been reissued.
Re means again but would not cause confusion with another word so no hyphen.
Example: I must re-press the shirt.
Re means again AND omitting the hyphen would cause confusion with another word so hyphenate.
Pop Quiz
Select the correct answer:
1A. Please call the restaurant to reserve a table.
1B. Please call the restaurant to re-serve a table.
1C. Please call the restaurant to re serve a table.
2A. I resent the file to you last night.
2B. I re-sent the file to you last night.
2C. I re sent the file to you last night.
3A. I’ll print out the letters again, and you can resign them.
3B. I’ll print out the letters again, and you can re-sign them.
3C. I’ll print out the letters again, and you can re sign them.
Answers:
1A. Please call the restaurant to reserve a table.
2B. I re-sent the file to you last night.
3B. I’ll print out the letters again, and you can re-sign them.
Posted on Tuesday, March 30th, 2010, at 9:06 am

Can anyone help us solve a raging debate at our company relating to hyphens?
Do we use toll free conference calling OR toll-free conference calling?
…Jerry
toll-free conference calling
“Toll-free” is acting as one idea in front of another adjective.
So useful, thanks!
You are welcome.
What about rerule? Is that even a word? or should it be Re-Rule? having a fight in scrabble!
Thanks
None of the dictionaries that I have consulted list it as a word in the English language.
I do not agree with the given answer on number 9 in the quiz: reinjured vs. re-injured. Upon initially reading the word “reinjured”, it COULD be misconstrued as “rein”; I think here, it is appropriate to put the hyphen after “re-”.
Even if misconstrued as “rein,” it still would not form another word. Reinjured is a valid word which you can find listed as a “related form” to injure on Dictionary.com as well as in The Official Scrabble Players Dictionary.
Is it reintegration or re-integration? If it’s hyphenated, is the ‘i’ capitalized or not?
The word reintegration does not have a hyphen.