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I am looking for sources for the segula of baking challah on behalf of a sick person, a shidduch, a baby or even a World Series victory. Where does this come from? Why can men not be part of it? Why does it have to be done at a specific time? etc.

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You might want to look at "Shabbos Secrets", by D. Meisels. I don't have it, but I've seen it, and it's got pictures in the back of any type of customary challah you can imagine. Maybe he discusses the significances in the book itself. amazon.com/Shabbos-Secrets-Rabbi-Dovid-Meisels/dp/1931681430 – jake May 13 '11 at 16:22
Who said men can't be part of it? – Baal Shemot Tovot Mar 28 '12 at 21:44
Baking Challah is a Segula for avoiding hunger. – Double AA Jan 27 '15 at 2:57

There's the whole key-challah thing that's supposed to be a auspicious for making a living. See more about it here and here (summarizing from this mp3), including notable rabbis who think it's downright prohibited.

The baking segulah I'd heard was to bake your own challah for Shabbos rather than buying it, as a segulah for your children finding the right person and getting married. Or so I've heard it.

Regarding baking in general, there is a Gemara (which appears to be in the realm of Agada as it's not cited directly by Rambam or Shulchan Aruch, as far as I can tell) in Bava Kama 82a:

Ezra made ten enactments ... [#6] that a woman wake up early and bake [bread] ... why? Because poor people might show up

-- and this way she'd have something readily available to feed them. (There's a story in Taanis about having food on-hand for poor people.)

So this challah segulah is sort of my favorite type of segulah:

  • It traces back (to some degree) to a solid Talmudic foundation
  • It's not asking for anything too weird, crazy, or pagan-looking
  • It encourages healthy behavior that may, on its own, influence the desired outcome

Hopefully if a family can manage their house well enough to bake their own challah, that will be a good environment for their children to learn healthy relationships. (I say hopefully). Alternatively -- the mom is so busy baking challah that she stops meddling? :)

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