Accept payments created outside of Quicken into register - not correct

DLCPhoto

I have used Quicken for Windows for decades, and started seeing this problem around 6 months ago.

I initiate various online payments (Credit Card, Utility, etc.) within Quicken: I have Online Payees configured with my bank (Fifth Third), use the "Send" option within Quicken, these transactions are sent to the bank, and at the appropriate date, the payments are sent.

When I do an Online Update, the transactions which have been paid then (most of the time) appear in the 'Downloaded Transactions' listing that appears at the bottom of the register, I click on each one, they automatically match with the original transaction, and everything is good.

The problem is that after doing an Online Update, in the Downloaded Transactions section at the bottom of the register, I now sometimes see some of these transactions in a section labeled

"Accept payments created outside of Quicken into register"

I then have to click on each one, and manually match it to the register transaction, since it doesn't happen automatically. Despite the fact that the original transactions is already in the register - exact same Payee, Date, Amount, etc. - it doesn't recognize it or automatically match it, and tries to enter a duplicate. I have to avoid that by manually matching it to the correct transaction.

After matching these, it then shows "Continue" at the bottom right, which then brings me to the usual list of Downloaded Transactions, where I can click and match as usual.

So these transactions it is seeing as having been "created outside of Quicken" were in fact absolutely created within Quicken, as I have done it for decades. It creates additional and needless work to get these properly matched.

I have tried:

Validate
Super-Validate
Did a File Backup, and then restored from that Backup

No matter what I do, it continues to show some of these online payment transactions (not all) as not having been created within Quicken, when in fact they were.

I have done a phone call with support, and was told they would escalate this to Tier 2, but I haven't head anything back. Very frustrating.

Am I the only one seeing this?

Tagging @Quicken Anja as you have been helpful with a couple of other questions and problems I've run into.

Quicken Anja

Hello @DLCPhoto,

Thank you for the detailed explanation—that’s very helpful!

To better assist, could you please confirm when you contacted Support about this specific issue? Was that a recent interaction?

Also, if possible, please provide screenshots showing what you’re seeing—specifically the section labeled “Accept payments created outside of Quicken into register” and how those transactions appear before and after you manually match them.

If needed, please review this Community FAQ for instructions on how to attach a screenshot. Alternatively, you can also drag and drop screenshots to your response if you are not given the option to add attachments.

This will help us review the behavior more closely and determine next steps.

Thank you!