Single-digit, three addend sums of the type a + b + c offer a rich opportunity to directly observe the range of strategies that different participants may use because they afford the possibility of measuring a partial sum (i.e., a + b or a + c or b + c). For example, while computing the sum 9 + 7 + 1, do participants go in order by first adding 9 + 7 and then adding 1, or do they incur the cost of going out of order by adding 9 + 1 in order to obtain the partial sum of 10, which makes the subsequent addition of 7 less effortful? Informed by findings in simple and complex arithmetic, we investigated the problem types and participant characteristics that can predict out of order switching behavior in such three-addend sums. To test our hypotheses, we tasked participants, first in an online study, and then in an in-person study to complete 120 single-digit, three addend problems. We found that participants switched the order of addition to prioritize efficiency gains in contexts in which the partial sum addends were small or equal to each other, or when doing so led to a partial sum of 10, or led to a partial sum that is equal to the third remaining integer. Response latency data confirmed that participants were deriving efficiencies in the manner we expected. Related to individual differences, our findings showed that participants with higher levels of math education were most likely to seek efficiency benefits whenever they were on offer.