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Are constructs using a slash combined with a hyphen to switch a prefix such as in "on-/offline" as a short-form of "online/offline" (or rather "on-line/off-line") which again stands for "online or offline" (which could be written as "on- or offline") something a native English speaker reader would understand right away?

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    I think it depends on how familiar readers are with the words in which you're thinking of using a suspended hyphen. – JLG Aug 22 '17 at 14:49
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It would be understood. However, this is a style issue. There are style manuals one may follow. I use the Chicago Manual of Style.

In formal writing, slashes and parentheses are frowned on; such as 24/7, (s)he, he/she, and/or and on/offline.

However, things having slashes or parentheses as a convention are alright: on/off switch, fractions, area codes, interpolations, etc.

Sentences with examples similar to yours should be rewritten to retain meaning. An additional problem is non-native speakers could be confused.

Try,

I am going online and offline as soon as I get home and find out where I'm at.

Documents can be printed either online or offline.

However, in less formal writing, you don't have to be too careful with style as long as your target audience understands your message.

Still, because online and offline are not hyphenated in modern dictionaries, you wouldn't hyphenate in your construction.

off/online or on/offline are accepted, but on-/offline looks awkward to me. A construction where the words in question would normally be hyphenated would be an exception: para-/ortho-oxygenated side chains

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    I'm trying to work out whether the less awkward-looking on-/off-line (in that both parts are hyphenated) outweighs the fact that neither would normally be hyphenated. Did they evolve from on line through on-line to online the way tomorrow did? – TripeHound Aug 22 '17 at 15:33
  • OK, so basically the hyphen does not need to be added or even shouldn't be added since it should be clear from the context that e.g. on/offline does not refer to on or offline but on or offline. Note that theoretically switching a suffix would also be possible (I can't think of any English example right now) but again the context should make things clear. – phk Aug 22 '17 at 17:47
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    As you say, the problem is ambiguity. On/offline [+/- the hyphen] could mean: 1) Online and offline; 2) Online and then offline; 3) Online or offline; or 4) Online but then offline. Rewording is the best option. – Stu W Aug 23 '17 at 1:02
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    Of possible interest: Google's n-grams for on line/on-line/online and off line/off-line/offline both show the two-word version was used first; the hyphenated version taking over either side of 1960 and the one-word version dominating from 1980 (online) and mid-1990s (offline). – TripeHound Aug 23 '17 at 6:47

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