I am having increasing trouble with the register line that has been posted from the manage bill & income function and what is downloaded from the bank and/or brokerage. One of our SS checks comes in 3rd of the month, but if the 3rd is on a Saturday or Sunday - the feds deposit on the Friday before. I suspect that Quicken first looks at the date and then looks at $$ and no match on a date & $$, Quicken inserts a new line entry. But the entry from manage bills has some monthly automatic deduction, which the new line entry doesn't have. We also get an SS check on the 3 Wednesday of the month, so that check can be deposited anywhere from the 15th to the 21st. I have auto ACH transfers from Chas Schwab to our PNC bank account twice a month. Schwab doesn't have the function to transfer every 2 weeks to keep the deposit on a business day, but the transaction date in Schwab is on the day of the transfer and the PNC date in the register the date it received it, making the transaction show up one day apart. When I go to reconcile accounts at the end of the month, accounts don't tie out and I have to go and track down the reason(s).
Would suggest that the software starts looking for $$ and +/- 7 days of the date. If only one matching $$$ in the register, presume that it is a match and/or put a notation in the uncategorized transaction section on the home page. It seems the more I try to automate transactions, the more I have to manually correct, which IMO should be handled by the system.