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What is the word in each case?

  1. I can attach or cut.
  2. I can be virtual or real.
  3. I can approve or penalize.
  4. I can separate or entangle.
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Four words that satisfy these double definitions are:

1. I can attach or cut.

CLIP (and also CLEAVE, courtesy of @msh210 in comments)

2. I can be virtual or real.

LITERAL(LY) ('virtually' when used in the colloquial sense...)

3. I can approve or penalize.

SANCTION (and also ENDORSE, albeit more commonly in the UK in the context of driving licence penalty points re the 'penalize' definition)

4. I can separate or entangle.

RAVEL

In fact, there's a word to describe words like these:

Auto-antonyms - words with multiple meanings which are the reverse of one another.

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    $\begingroup$ Absolutely correct! I was quite pleased when I discovered the existence of these words. $\endgroup$ Commented Jul 21, 2021 at 14:18
  • $\begingroup$ @DmitryKamenetsky I toyed with rot13(RAQBEFR) for the third one also, since in the UK we use that word to describe both backing a candidate and adding penalty points to a driving licence, but I figured the one I went for was probably more internationally known... $\endgroup$
    – Stiv
    Commented Jul 21, 2021 at 14:20
  • $\begingroup$ Oh I didn't realize that word could also mean penalize. Interesting. Perhaps worth adding a note to the Wikipedia entry. $\endgroup$ Commented Jul 21, 2021 at 14:22
  • $\begingroup$ #1 can also be rot13(gb pyrnir). $\endgroup$
    – msh210
    Commented Jul 21, 2021 at 15:44
  • $\begingroup$ @msh210 That's true - I'll add that as an additional option, thanks. $\endgroup$
    – Stiv
    Commented Jul 21, 2021 at 15:55

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