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As a rule, there shouldn't be anything that is a separation between a man's head and the tefillin, so seemingly a wig would be a problem. In Igros Moshe Orach Chaim Chelek 4 Siman 40 Ois 18, Rabbi Moshe Feinstein addresses the question of someone who wears an easily-removed wig at all times and would be embarrassed to remove it in the synagogue. He says that such a person should put on the head-tefillin in the synagogue, while wearing the wig, without saying the bracha, and that later, at home, he should put on tefillin without the wig and with the bracha. Are there any makilim (lenient halachic decisors) in this matter that permit someone to put on the tefillin lichatchila, with a bracha, over a wig, in a case in which asking the person in question to do this double wearing may be asking too much?

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This is a really good question for this forum but for practical advice (esp. since it seems like a specific case and one that involves some very personal issues) please see your rabbi. He'll likely be more sensitive to the situation as a whole. – Charles Koppelman Sep 19 '12 at 13:57
Although this is a practical shailo it's not my shailo (or that of my son or any family member) I only heard it today from a Rov that was dealing with it. The olam shouldn't feel to hold themselves back from trying to answer the question or provide additional sources. – Yehoshua Sep 19 '12 at 14:39
@CharlesKoppelman, I've generalized the question. – Seth J Sep 19 '12 at 17:29

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