Tefillin on Chol HaMoed

There was a shiur on this topic on YU Torah but it doesn't appear to be there anymore so I'll write what I remember from it.

A person doesn't wear the twa of tefillin on shabbos and yom tov since they are an twa themselves.
Q: Is Chol HaMoed an twa and patur from tefillin?
A: Possibly. If it depends on the mitzva of yom tov, then chol hamoed is also, since you can’t eat out of the succah all of succos and you can’t eat chometz all of pesach. But if it depends on whether there’s an issur melacha, then it’s a question. Is the issur melacha d’oraysa and therefor it is an twa or is it just d’rabanan (and wouldn’t prevent the d’oraysa of tefillin)?

So if each possibility was a 50% chance, there would only be a 25% chance that chol hamoed is not an twa and patur from tefillin. Most of the Ashkenazi rishonim held like this and that’s how the Rema paskens. He says you wear tefillin on chol hamoed and make a bracha, just say it quietly (just in case there are Hassidim in the back).

But other poskim say no, you shouldn't wear tefillin on chol hamoed. Either because twa goes by the mitzvas yom tov or because the issur melacha is d’oraysa. The shulchan oruch says you’re not allowed to wear tefillin on chol hamoed, because twa of shabbos and yom tov doesn’t just permit not wearing tefillin, it makes it assur. The zohar says someone who wears tefillin on chol hamoed is chayiv misa.* The Vilna Gaon also says [the Rema is very wrong and] you shouldn’t wear tefillin on Chol hamoed.

So according to some it’s a chiyuv d’oraysa and according to others it’s assur d’oraysa. The Mishna Berurah, quoting the Ba’ch, suggests a compromise. Put on tefillin, but make a condition before putting them on: Say “If really there’s no mitzvah, I’m not doing anything now; these are just expensive bits of leather I’m wrapping around my arm.” Without the intention of doing a mitzvah, you won’t be doing any issur, even according to the shulchan aruch. Then you say “If there is a mitzvah then obviously I’m doing the mitzvah of tefillin!” That way you’re safe either way and you can put on teffilin, you just don’t make a bracha since you’re in doubt .

The mishna berurah says everyone should follow their custom, just make sure you don’t have some people wearing and some people not wearing tefillin since then it’s “Lo Sisgod’doo. R’ Moshe says elswhere (by which half of sefirah to keep) that in America, this isn’t a concern, since there is no minhag America, everone came with their own customs. In Europe, each town or area had its own minhagim, and it would be wrong to do differently. But in America everywhere’s “Lo Sisgod’doo”. So probably everyone can follow their own minhag for tefillin on chol hamoed also. Just don’t go to a minyan that does have a minhag and not follow it. (Don’t wear tefillin to a Hassidic Minyan, they take the zohar literally!)


* The Rema says this Zohar means only if he wears Tefillin and kills someone would he be chayiv misa.