Downloaded transactions aren't matching with corresponding Check Pay register entries

Makers

I'm running Quicken Premier 2020 Version 5.15.3 (Build 515.33035.100) on my Mac running Catalina OS X 10.15.3. I've started to pay bills within Quicken using Check Pay. Why doesn't Quicken match the check to the corresponding entry/transaction in my register when the check clears and is downloaded from my bank? Each time I must manually mark the transaction "cleared" and delete the downloaded transaction as a duplicate.

UKR

Makers said:

Thanks @UKR, that worked but unfortunately it lost the check number in the process. Does it matter which transaction I drag to the other? That is, will I get the same result if I drag the Check Pay entry over the downloaded transaction or vice versa?

I don't know about loss of check number on drag and drop. Not being a Q Mac user myself (I'm just a frequent flyer in the Community), I can't say. The wording in discussions always is something like "drag downloaded transaction over register transaction". If you can, try the other way, too, and see what that does.
IMHO, a paper check's number entered in a register transaction should not be overwritten by downloaded information. I don't know how that's supposed to work with online Bill Pay transactions, though.

ChicagoGuy

Don't know if it's your case but I've seen that happen when the dates of the two are more then a couple days different. If I update the entered registry date to the downloaded xaction date, the download xaction changes to show Matched.

Makers

I tried your suggestion but all that did was move the Check Pay transaction up in the register to be next to the corresponding downloaded transaction. Unfortunately Quicken still doesn't recognize it as one and the same transaction.

UKR

In Quicken Mac, if a downloaded transaction can't be matched to an existing register transaction, you can drag the downloaded transaction over the register transaction to effect a manual match.

J_Mike

Free with @UKR - dog and drop to match - do not delete the duplicate.
QMac ";earns" when your matching effort.

Makers

Thanks @UKR, that worked but unfortunately it lost the check number in the process. Does it matter which transaction I drag to the other? That is, will I get the same result if I drag the Check Pay entry over the downloaded transaction or vice versa?

UKR

Makers said:

Thanks @UKR, that worked but unfortunately it lost the check number in the process. Does it matter which transaction I drag to the other? That is, will I get the same result if I drag the Check Pay entry over the downloaded transaction or vice versa?

I don't know about loss of check number on drag and drop. Not being a Q Mac user myself (I'm just a frequent flyer in the Community), I can't say. The wording in discussions always is something like "drag downloaded transaction over register transaction". If you can, try the other way, too, and see what that does.
IMHO, a paper check's number entered in a register transaction should not be overwritten by downloaded information. I don't know how that's supposed to work with online Bill Pay transactions, though.

Makers

Thanks for your help!