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If I don't have a known family minhag regarding this, how should I decide whether to wear tefillin during Chol HaMoed? Which communities generally follow each option, and what are the reasons behind each?

Also, does it make a difference if I am in Israel (either for a visit or permanently)? I hear that in Israel as a whole there is a pervasive and strong disposition not to wear tefillin during Chol Hamoed. And if I am supposed to wear tefillin, what would I do on 2nd day on Yom Tov if I am visiting Israel?

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Did you wear tefillin during the last time it was chol hamoed or not? If so, then that is your minhag, but if not, then no. Because either way you have been fulfilling one of the minhagim, and both are acceptable and in accordance with halacha. –  Adam Mosheh May 23 '12 at 0:38
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Oy. Very tough question. Both Minhagim are very adamantly held positions, and they are mutually exclusive. CYLOR! –  Seth J May 23 '12 at 2:09
    
@SethJ They don't have to be mutually exclusive, if you put on tefillin with no bracha and a tnai. –  Double AA May 23 '12 at 15:15
    
@DoubleAA, those are sort of quirky Halachically wishy-washy solutions to a very complex problem. But on paper, the two positions are mutually exclusive. You're only wearing Tefillin on condition that it's what you're supposed to do? That's like saying I'm only eating this cheeseburger on condition that the meat is soy. –  Seth J May 23 '12 at 15:26
    
@SethJ I agree it is complex, and clearly most people stick to their respective minhagim lechumra and lekula, but I disagree with your analogy to cheeseburgers: that is a lav while here it is an asei where mitzvot tzrichot kavana is a very relevant factor. What I described is an opinion that has been held by various rishonim and achronim, and I think deserves to be brought to the table. –  Double AA May 23 '12 at 16:11
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Regarding Israel, the (virtually) universal minhag is not to put on tefillin here. Some people may put on privately at home, but no one wears in shul. If you are living here, you should adopt this minhag; if you are visiting, you should adopt it at least in public. Assuming you are keeping two days of yom tov, then on the 8th day of yom tov you will say the yom tov davening and not wear tefillin.

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Mike, Welcome to mi.yodeya, and thanks very much for bringing your Israeli knowledge to the Launch Party. –  Isaac Moses Mar 3 '10 at 15:19
    
"If you are living here, you should adopt this minhag" -- you mean in public? Or one should change his minhag even in private if he moves to Israel? –  Curiouser May 23 '12 at 1:47
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There are minyonim where tefillin is worn in public on chol hamoed in Eretz Yisroel, e.g. minyan affiliated with Machon Moreshes Ashkenaz. There are also significant elements who. though they may not wear them publically, do put them on in private, including gedolei Yisroel.

There is really no single, unitary 'minhag Eretz Yisroel' in general, by the way. Sepharadim in Eretz Yisroel don't act the same as GR"A followers, who don't act the same as Hassidim, and on and on....

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Nevertheless at least with respect to tefillin-wearing on C.H., I believe Mike is correct. When I was sojourning in Jerusalem one Sukkoth, I was told to wear tefillin in my apartment, since the "minhag Yerushalayim" is not to wear. –  Barry Mar 17 '10 at 16:08
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It was Reb Moshe Feinstein who said in Eretz Yisroel the Minhag is not to and hence only to wear them in Private. –  SimchasTorah Apr 2 '10 at 4:33
    
Usually there is no unitary 'minhag Eretz Yisroel', but with regards to tefillin on chol hamoed, the original groups there all had one minhag - (the sefardim there and the talmidei hagra and chassidim all didn't wear it.) –  Ariel K Sep 24 '13 at 16:54
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There are places where tefillin is worn in public on chol hamoed in Eretz Yisroel. For example, the Erlauer Rebbe does so in his beis midrash, minyan of Machon Moreshes Ashkenaz does so, and I think others as well.

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As far as I know, people who follow the Rambam wear tephilin on Chol HaMoed. This includes both modern Rambamists and Baladi Yeminites. As others have noted, there are also many individuals who follow this practice in private.

It seems that the universal practice was to wear tephilin on Chol HaMoed until the time of the Zohar. Quoting from an aquaintance of mine who follows Rambam in all matters:

the halakhic source by which tefillin on Hol haMoedh is forbidden, the ShulHan Arukh, breaks its own rule: As is well known, Rav Yosef Karo built the Sh"A according the majority opinion between RaMBaM, the Ro"sh (Rabbenu Asher), and the Ri"f (Rav YiS'Haq Alfasi). In this ruling, he IGNORES THE OPINION OF ALL THREE (that tefillin is worn on Hol haMoedh) and rules according to Zohar.

I have heard that one who has no minhagim, or who converts should take the Yeminite customs since many consider them to be the most historically accurate / pure.

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See here judaism.stackexchange.com/questions/22156/… Suffice to say that everyone thinks their minhagim are the best for newcomers, so your logic is currently not very compelling –  Double AA Sep 24 '13 at 17:00
    
Why was this marked down? As far as I know it is completely accurate. The part about what minhag to adopt is simply another opinion among many, and just as valid as other opinions presented here. –  Robert S. Barnes Sep 24 '13 at 18:49
    
In fact the answer to the question you referred to says: "The point is, there really isn't a set rule on this issue and the convert has relative freedom to choose." –  Robert S. Barnes Sep 24 '13 at 18:55
    
Why are you asking me ("you referred to")? I didn't mark you down. You should know, though, that accurate claims can sometimes be downvoted as not helpful if they are not sourced well. You are just another random internet user after all. –  Double AA Sep 24 '13 at 20:08
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