Advanced Regrouping in Multiple Columns

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What does it mean to have 'multiple regroupings' in one problem?
It means you have to carry a number in more than one column. For example, carrying from the ones to the tens, AND from the tens to the hundreds.
$$168 + 257 = ?$$
$$\begin{array}{rr} & 168 \\ + & 257 \\ \hline & 425 \end{array}$$Ones: \(8+7=15\). Write \(5\), carry \(1\). Tens: \(1+6+5=12\). Write \(2\), carry \(1\). Hundreds: \(1+1+2=4\).
$$399 + 499 = ?$$
$$\begin{array}{rr} & 399 \\ + & 499 \\ \hline & 898 \end{array}$$Ones: \(9+9=18\). Write \(8\), carry \(1\). Tens: \(1+9+9=19\). Write \(9\), carry \(1\). Hundreds: \(1+3+4=8\).
$$87 + 95 = ?$$
$$\begin{array}{rr} & 87 \\ + & 95 \\ \hline & 182 \end{array}$$Ones: \(7+5=12\). Write \(2\), carry \(1\). Tens: \(1+8+9=18\). Write \(8\) in the tens place and the \(1\) in the new hundreds place.
What happens when you need to regroup from the hundreds column?
The carried digit moves to the thousands place. For example, \(12\) hundreds is the same as \(1\) thousand and \(2\) hundreds.
$$678 + 543 = ?$$
$$\begin{array}{rr} & 678 \\ + & 543 \\ \hline & 1221 \end{array}$$Ones: \(8+3=11\). Write \(1\), carry \(1\). Tens: \(1+7+4=12\). Write \(2\), carry \(1\). Hundreds: \(1+6+5=12\). Write \(2\), carry \(1\) to the thousands place.
$$99 + 99 = ?$$
$$\begin{array}{rr} & 99 \\ + & 99 \\ \hline & 198 \end{array}$$
$$456 + 789 = ?$$
$$\begin{array}{rr} & 456 \\ + & 789 \\ \hline & 1245 \end{array}$$
When solving \(247 + 385\), which columns will you need to regroup in?
Both the ones column (\(7+5=12\)) and the tens column (\(1+4+8=13\)). You will regroup twice.
$$999 + 2 = ?$$
$$1001$$
$$586 + 627 = ?$$
$$1213$$
$$88 + 88 = ?$$
$$176$$
$$249 + 155 = ?$$
$$404$$
$$765 + 345 = ?$$
$$1110$$
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