I've had an ongoing issue between a checking account and a Fidelity account that I can't figure out how to resolve. My checking account is not connected to allow for automatic updates. My Fidelity 529 account is connected. Every week, I send money to Fidelity from checking. In my registers, I'm showing this as a transfer. When Quicken updates, it auto matches on the Fidelity register with the blue pencil and blue dot. However, it also always writes a new line item to my checking account for this, so it duplicates what I already have in there as a transfer and requires deletion every week.
The reason I don't have my checking account set up to sync is because it's just a holding account for a lot of transfers out, some of which take days to process and occur weekly. It starts feeling messy, at least in the past, because things either wouldn't match based on the date being 3 days different, or would update the date on the overall transfer and then cause one of the registers to be incorrect. I honestly don't recall the specifics from doing this years ago, but it was too messy to deal with - maybe it's better now with the new matching stuff that was recently released.
What's the best move here to prevent the weekly dupes in my checking register?
