May
/meɪ/ (n., modal v.)

  1. (n.) A month which promises much but so often disappoints.
  2. (n.) A prime minister who did likewise.
  3. (modal v.) A modal verb which expresses optionality, but is commonly articulated by lawyers as “shall be entitled” or, if they want to be bloody minded it (and which lawyer does not?) “may, but shall not be obliged to”. Or even “may, but shall not be obligated to”.
Towards more picturesque speech
The Unbearbable Tension Between Compulsion And Choice (von Sachsen-Rampton, 1906)
SEC guidance on plain EnglishIndex: Click to expand:
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May” confers an discretion, not an obligation. There is one time that you should use this expression in a contract: when you are conferring on a party a right that party would not otherwise have.

To wit: “Party A may cross Party B’s private land to access the roadway” is a good use of the word “may”.

“Notwithstanding anything contained in the foregoing [which is about something else altogether], and for the avoidance of doubt, Party B may telephone his elderly aunt at any time without limitation” is not a good use of “may”, or the trees on which such a pointless sentence may, for the time being and from time to time, be printed.

Shall be entitled to

Shall be entitled to” means, exactly, “may” — they are exact synonyms — but it is so much worse a piece of legal psychology.

How so?

Because it is so in your face. First, it uses that equivocal staple of fusty compulsion, “shall” — but, however redundant the construction might otherwise be, it involves no compulsion.

Second, then it talks, gratuitously, in terms of entitlement. It acts “all entitled”. Now perhaps this is just me, but this has the air about it not of the gentle citizen pottering about her own plot of land, equably and quietly enjoying her rights in a way calculated to offend no-one. Rather it is the wilfully aggravating disposition of bloody-minded troll, marching up and down her boundary, wantonly provoking passers-by with a loudhailer.

For an essay on the modern fear being conferred a choice, see discretion.

See also