I have the same problem and it is the program, not my reconciling. My wife is an accountant, there are no missed transactions it is the software. Let me explain:
Randomly, and with different accounts, The amount in the cleared Charges column on the left does not match the "cleared Balance" on the right. The difference is ALWAYS -29.75. It doesn't matter what account and it doesn't happen to all of them (YET). I have spent hours on the phone with support, they tell me to start over with all new file. I have decades of data. The two numbers should simply be a spreadsheet column copy and for them not to match tells me the program, not the data is bad. This problem began under Quicken 2017 and continues under 2019. My wife has her own computer with her own program and data file and she has experienced the same thing, albeit only one time so far. It is maddening. I am tired of doing "adjustments" to make things balance as this is no way to keep proper books. Anyone else?