Although it's forbidden to make an interruption between putting on the tefilin shel yad and shel rosh (Shulchan Aruch 25:9)

אסור להפסיק בדיבור בין תפלה של יד לתפל' של ראש ואם הפסיק מברך על של ראש על מצות תפילין: הגה ולדידן דנוהגין לברך ב' ברכות אף אם לא הפסיק צריך לחזור ולברך על של ראש להניח וגם על מצות - It is forbidden to speak at all between putting on the two tefillin, and if he spoke, he must make the blessing on the head tefillin. Note: Since we [Ashkenazim] make two blessings, he must make both blessings on the head tefillin

since my minhag is to put on tefillin without a bracha on Chol haMoed, would I be able to make a hefsek between the tefillin shel yad and shel rosh? (By answering kaddish)

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    Why would it be permitted to interrupt? Your source says clearly it's forbidden to interrupt between the two Tefillin. – Double AA Sep 28 '18 at 19:08
  • The source seems to partially imply that the issue was in the brachos – NJM Sep 28 '18 at 22:10
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    That's awfully vague. Which words imply what issue? Edit your question to clarify instead of leaving important info in the comments. – Double AA Sep 28 '18 at 22:12

The Mishnah Berurah there (s.k. 28) explicitly addresses your question.

ואפילו לאותן המניחין תפילין בחוה"מ בלי ברכה או המניחין תפלין דר"ת אחר שחלץ תפלין דרש"י או שחלץ תפלין ע"מ להחזירן דהרמ"א בסי"ב פסק דא"צ לחזור ולברך כשמניחן אח"כ אפ"ה עבירה היא להסיח ביניהן דלכתחילה בעינן שיהיו סמוכין ותכופין זה לזה דכתיב והיה לך לאות על ידך ולזכרון בין עיניך שיהא הוייה אחת לשתיהן

Even those who wear tefillin on Chol HaMoed without a blessing, or those who wear Rabbeinu Tam tefillin after they've already worn Rashi's tefillin, or someone who takes off tefillin with intention to put them back on (which the Rema in Seif 12 rules that one doesn't make another blessing) and puts them on later, even so it is a transgression to speak between them. This is because ideally we need the two tefillin to be connected and adjacent to each other, as it is written: "It shall be for you as a sign on your arm and a remembrance between your eyes", that they should have the same "being" for the two of them.

In Shaar HaTziyun he cites the Magen Avraham (s.k. 14):

ואפי' לאותן המניחין בח"ה בלא ברכה אפי' הכי עבירה היא להסיח (ב"י מהרא"י)‏

Even those who wear tefillin on Chol HaMoed without a blessing, even so it is a transgression to speak.

The Magen Avraham cites the Beis Yosef (ad. loc.) and Terumas HaDeshen (#107) (who the Beis Yosef brings).

While the Pri Megadim (Eishel Avraham ad. loc. s.k. 14) says that on Chol HaMoed, since no blessing was said, one can answer "Amen yehei shmeih rabah" in Kaddish between the two tefillin, he points to what he wrote in s.k. 17. There he brings the reason of having the two tefillin be connected, and therefore forbids saying even amen yehei shmeih rabah. The Pri Megadim (Mishbetzos Zahav ad. loc. s.k. 4) says this idea comes from the Ba'al HaMeor at the end of Rosh Hashanah. This is where the Mishnah Berurah got his explanation from.

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In a lecture about wearing tefillin on Chol Hamoed (starting at approximately 8:26 into the recording), R. Aryeh Lebowitz said as follows:

Now if you happen to put on tefillin without a beracha like the shitas haTaz, so the whole thing about not being mafsik between the beracha that you say on the shel yad until after you finish putting on the shel rosh – even for amen yehei shemei rabbah, and amein, and kedushah and barechu – so that won't apply. You would then be allowed to answer for all those things in between the shel yad and the shel rosh. You may need to again adjust the shel yad afterwards to make the connection between the shel yad and the shel rosh but you would be allowed to answer to all those things.

His point seems to be that even if there needs to be a connection between the shel yad and the shel rosh, the connection can be established after the interruption. Normally this can't be done because it would be an interruption between the beracha and the mitzvah, but in this case that issue is moot.

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  • Not to argue on his suggestion, but what then is the Mishnah Berurah (quoting earlier sources) saying when he says its forbidden to interrupt? Why not just interrupt and "fix it" later? – robev Oct 5 '18 at 4:02
  • @robev I assume he is understanding the Mishnah Berurah to mean that you can’t orchestrate a situation where the shel rosh is disconnected from the shel yad. You can avoid that by reputting on the shel yad. (I.e. there is no independent issur in hust putting on a shel yad and taking it off.) – Alex Oct 5 '18 at 4:21

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