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Missing transactions from previously reconciled months

I searched and found an old discussion or two, but nothing that seemed to fully address the issue I'm seeing...
Two or three times a year, I discover that a Quicken account balance does not match the reconciled online balance. Though I reconcile my accounts regularly, I find that suddenly several old transactions are simply missing. This results in me spending the better part of an afternoon searching through 18+ months of transactions and statements to find about six missing transactions - as happened to me last week.
I tend to find that the missing transactions are ones for which there was a second similar charge on or about the same day. For example, our daughter rides Bird scooters, and the charges all tend to be the same amount (eg $5.00) and similar payee (Bird includes the date in the "Statement Payee", eg "CHECKCARD 0706 BIRD APP"). She will ride the scooter twice in one day, or on consecutive days, and one of these transactions will be missing.
Again, this is going back as far as 18 months and beyond, several little transactions, after several months of perfectly reconciled accounts. I believe this always happens with our debit accounts, but I can't be certain.
I saw one thread that suggested this is a possible issue with cloud sync, but not conclusively.
Though it tends to be relatively low totals (like $30 or $40 total), for which I could easily make an adjustment, it really worries me that transactions simply disappear.
Does anyone have any insight into this?
I'm running Quicken for Mac 2020, Deluxe, version 5.18.2, on macOS 10.15.7, but this issue has been happening for years through several versions.
Two or three times a year, I discover that a Quicken account balance does not match the reconciled online balance. Though I reconcile my accounts regularly, I find that suddenly several old transactions are simply missing. This results in me spending the better part of an afternoon searching through 18+ months of transactions and statements to find about six missing transactions - as happened to me last week.
I tend to find that the missing transactions are ones for which there was a second similar charge on or about the same day. For example, our daughter rides Bird scooters, and the charges all tend to be the same amount (eg $5.00) and similar payee (Bird includes the date in the "Statement Payee", eg "CHECKCARD 0706 BIRD APP"). She will ride the scooter twice in one day, or on consecutive days, and one of these transactions will be missing.
Again, this is going back as far as 18 months and beyond, several little transactions, after several months of perfectly reconciled accounts. I believe this always happens with our debit accounts, but I can't be certain.
I saw one thread that suggested this is a possible issue with cloud sync, but not conclusively.
Though it tends to be relatively low totals (like $30 or $40 total), for which I could easily make an adjustment, it really worries me that transactions simply disappear.
Does anyone have any insight into this?
I'm running Quicken for Mac 2020, Deluxe, version 5.18.2, on macOS 10.15.7, but this issue has been happening for years through several versions.
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