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I have been putting on talit along with tefilin for over a decade, and I still frequently get the strap of my shel yad tangled in the one of the fore-tzitzit of my talit when I'm winding it around my arm. Once it contacts a tzitzit during its circular motion, they wind together until I notice, and then I have to either unwind them or pull the remaining length of the strap through the talit strings to extricate it.

What technique works well to prevent this tangling from happening? Please indicate in the answer post whether you have used the technique and how well it works for you.

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    Pull your front Tallit-bits very low when putting it on. I'm not posting as an answer because until I do it again tomorrow morning I can't say what I actually do to alleviate this issue. – Double AA Dec 1 '14 at 0:13
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    All I can say is that I have the same problem. Reminds me of the old addage, "Ah! Tosefos asks the same question!" It may not help with your answer, but somehow makes you feel better... – Jeremy Dec 1 '14 at 18:23
  • @Jeremy, I confess that comments like yours and those in most of the answers to date do, in fact, feel gratifying. It feels good to be in good company! – Isaac Moses Dec 1 '14 at 18:28
  • @DoubleAA Are you ready to answer yet? :P – Shokhet Dec 4 '14 at 21:40
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    I won't post an answer, because this isn't something that I do myself, but I've seen people put on their talis, and then take the half that belongs on their left shoulder, put it on their right shoulder, and put it back when they're done putting on their tefillin. – Shokhet Dec 4 '14 at 21:42
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Going on ten years and I'm proud to say I'm a recovering twister. There is one thing that I find helps. Putting on the tephilin slowly and carefully. It seems this would usually happen when I was late and in a rush, and like you say by the time I looked down to see what was going on, it was too late.

Going slow has worked for me.

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I hold both my hands far from my body when winding the shel-yad strap, and make sure the nondominant-hand side of my talis lies on my chest and the top of my shoulder, not on my arm. Then the two don't mingle.

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As a disclaimer, I still have this problem, and I got much consolation from seeing it once happen to R' Tzvi Berkowitz, who has been putting on a tallis and tefillin for around 4 decades.

What has mitigated the issue for me, is to put my shel yad strap draped over the chair in front of me as I wrap it, so that it doesn't droop near my tallis strings. Then as I wrap, it winds up while remaining draped over the chair. Once it is no longer long enough to drape, it is no longer long enough to reach down to my tallis strings.

I usually have the problem more as I take my tefillin off, at which point I try to do the same thing, but for some reason when taking off the shel rosh it seems to go awry.

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I never encountered this problem, and, no, I am not exaggerating, either. Perhaps, it may be that my daily tallit is relatively short (yes, it is the minimal required length, and, it is not a "shawl", if you're curious).

But, from your description, I can envision the problem. One suggestion - Most people fold part of the tallit over their shoulders so, at least 2 tzitziot are behind you. I assume that you're doing that. As for the front tzitziot, if your tallit is long enough, you may be able to tuck them into your belt, or top of the pants, temporarily. If not, perhaps, wear the tallit diagonally (similar to how I have seen many people wear their jacket diagonally while wearing tefillin.) I.e. - if you're a righty so your tefillin is on the left hand, wear the right part of the tallit over the shoulder; the left part goes diagonally down the back and comes around the left front where you can tuck in both tzitziot (front and back) into your belt. After you have adjusted the tefillin, you can adjust the tallit.

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