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This may be two questions that are closely related.

Would engaging in war with 'Amalek without a specific command (a la Shaul) be a Milhemeth Mitzvah or Milhemeth Reshuth?

Is killing all of 'Amalek (as opposed to assimilating them, perhaps) a Mitzvah, or a Reshuth? If you had a choice, is total physical annihilation preferred over peacefully (or even forcefully) converting them all?

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Isn't that 3 questions? –  Double AA Jul 17 '12 at 4:59
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+1. But re "engaging in war with 'Amalek without a specific command (a la Shaul)", see Sh'muel 15:3. –  msh210 Jul 17 '12 at 6:10
    
The third is a rephrasing of the second. –  Seth J Jul 17 '12 at 12:12
    
Why wouldn't killing all of Amalek be a Milchemet Mitzvah? –  Daniel May 8 '13 at 19:12
    
@Daniel, the Mitzvah is the "erase their memory". Does that mean by war? Individual 'Amalekim are allowed to convert; why not the entire nation? See msh210's answer. –  Seth J May 8 '13 at 19:47
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up vote 4 down vote accepted

Minchas Chinuch 527 writes that the rules of any milchemes mitzva apply to Amalek: whether that means you allow them make peace before annihilating them is, he says, a machlokes rishonim.

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