When the ones digit we are subtracting is larger than the ones digit we are subtracting from, we need to regroup — trading 1 ten for 10 ones. For example, 53 − 27 requires regrouping in the ones column because 3 < 7: we borrow a ten, making the ones 13, and the tens column becomes 4. The total value of the number does not change; we are just representing it differently.
Start with base-ten blocks to show physically breaking apart a tens rod into 10 ones. Use the 'can I subtract?' check on the ones column as a decision-making habit. Compare with the counting-up strategy (counting up from 27 to 53 on a number line) so students see multiple valid methods.
You already know place value — that a two-digit number like 53 is made of 5 tens and 3 ones. You also know how to subtract within 20. Regrouping (sometimes called borrowing) is what happens when those two skills meet a problem they cannot handle separately: there are not enough ones to subtract from.
Consider 53 − 27. Start with the ones column: can you subtract 7 from 3? No, because 3 is too small. So you regroup — you trade one of the tens for 10 ones. The 5 tens becomes 4 tens, and the 3 ones becomes 13 ones. Now you can subtract: 13 − 7 = 6 in the ones place. Then subtract the tens: 4 − 2 = 2. The answer is 26. Crucially, the total value of 53 never changed — you just re-expressed it as 4 tens and 13 ones instead of 5 tens and 3 ones.
This mirrors what you learned in addition with regrouping, but in reverse. In addition, 10 or more ones bundled up into a new ten. In subtraction, a ten unbundles into 10 ones when you need them. The place-value structure allows both kinds of exchange because 1 ten always equals 10 ones exactly.
A useful habit: before subtracting, look at the ones column first. Ask "can I subtract?" If yes, proceed. If no, regroup first, then subtract. After regrouping, always update the tens digit — it drops by 1 — before continuing to the tens column. Forgetting that update is the most common error in the whole procedure.