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I hear the word should used a lot and its meaning can be vague. To illustrate how many times this occurs, from the single article Forty Hadiths for Women, the word should appears in:

woman should take the permission of her husband before going out; women should not travel without mahram; women should have their own entrance to the mosque; women should not walk in the middle of the street; women should perform tawaf without mingling with men; men shouldn’t enter freely into private places where foreign women are; women should have their own learning venues; women should not carry funeral; women should not take off their clothes outside their homes; woman should not describe another woman to her husband; women should not speak unnecessarily in the presence of foreign men; a woman should not be married against her will; a woman should not ask for divorce without a reason; woman should be grateful to her husband; woman should not obey her husband if ordered to do a sin; woman should not donate from her money unless upon husband’s consent; woman should help her husband and his dependants; husband should provide for wife and children; woman should not wear tight clothes; woman should not wear false hair like Jews; woman should not lie and adopt falsehood; women should not wear high shoes; women should cover her face in the presence of foreign men; women should not show their ornaments to foreign men; women should not imitate men in dress, movements, and way of speech.

If we compare, e.g.:

a. "woman should not obey her husband if ordered to do a sin", with
b. "women should not walk in the middle of the street"

we see the level of obligation is significantly different, but there is no corresponding change in phrasing. So I can't tell which of these things are actually important without studying the Qur'an, hadith, tafsir, and fatwa in detail, which takes time. And I'd need to do this for every one of these claims.

Question: How can I practically determine what should means?

Specifically, I'm seeking practical steps for those times when someone tells me or I read you should XYZ, and I want to know (a) if it's true and accurate, and (b) gauge the level of obligation.

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Muslim jurists generally distinguish between the following:

  1. wajib: Actions that are obligatory: not doing them is a sin.
  2. mustahabb or sunnah: actions that are desirable/praiseworthy, but omitting them is not a sin.
  3. mubah: actions that are indifferent, neither desirable nor reprehensible, neither commanded nor forbidden.
  4. makruh: actions that are not desirable, and it is best to refrain from.
  5. haram: actions that are forbidden, doing them is sinful.

There are also grey areas; so for example, one action may be 'mustahabb' (desirable) according to some interpretations and wajib ('obligatory') according to other interpretations, and so on.

You're right: should in English can be used for either wajib or mustahabb; and shouldn't could be used for either 'makruh' or 'haram'; knowing which is which requires further research.

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