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Why do some people have the custom to wind the Tefillin-Shel-Yad towards themselves, while others wind it away from themselves? What is the reason behind these two customs, and which sects of Judaism generally follow which method?

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Handy graphical guide to different customs: shemayisrael.co.il/tefillin/var.htm – jake Jun 16 '11 at 22:38

It's pretty much a question of which eida you come from:

Ashkenazim wind inwards, Sfaradim wind outwards.
(And, confusingly, right-handed ashkenazi using left-handed ashkenazi tfillin would also be winding backwards...)

The link that @jake posted in comments illustrates this very nicely - it depends on which eida's minhag you use.

(Sorry, I don't know the reasoning behind the different minhagim - though I find it likely that each do it that way, because thats the way they do it...)

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I wear tefillin made for people of the opposite handedness (for lack of better word) all the time, and I don't end up winding backwards. Am I doing something wrong? – Baal Shemot Tovot Mar 28 '12 at 5:00

In my (predominantly Ashkenazi) school where we learned about Tefillin, we were taught that the reason for wrapping inwards is that it is towards your heart, thereby making a statement (over the top...) of the love that you (... towards your heart) has for the mitzvah of Tefillin.

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