Quicken Users Often Experience Problems With Chase Bank Transactions

Quicken is an old-school personal financial management (PFM) software application that allows users to manage their banking from their own computer, rather in the cloud. Older (and wiser) computer users prefer a local software solutions because for something as important as banking, they want the local control if things go bad.

The 30+ year quicken personal finance software was created and owned by Intuit Software and was sold in 2016 to H.I.G. Capital, a Miami-based private equity firm, who have been struggling to make the software viable once more.

Quicken Acquisition By H.I.G. Capital in 2016 Fails To Resolve Ongoing Problems

A recent software upgrade from Quicken demonstrates that the new owners, H.I.G. Capital, have a great deal of problems making the software work properly and often rely on users to be their beta testers. This is not an isolated incident, as it is indicative of a culture of poor quality and failure to support customers and it is at the very hear of H.I.G. Capital’s problems.

What seems to be the problem is that the Quicken developers do not sufficiently test their software and they allow their own users to become the de facto beta testers.

Chase Bank Really Hates Quicken

The ongoing relationship between Quicken and Chase is often like a divorcing couple who live in the same house. They might have a cordial talk over breakfast, but when one of them sleeps with the neighbor, the whole wagon come off the rails. Things have gotten so bad that Chase Bank customers are often told by Chase phone representatives that Quicken is no longer supported or approved by the bank, but that story changes on who the support agent is. Even a quick search of the Quicken website forum https://community.quicken.com/categories/alerts shows that Chase Bank is the most encountered bank error, but Quicken does not seem to be listening.

Natalie the overzealous moderator at Quicken

Overzealous Community Admin ‘Natalie’ Deletes All Postings That Show Quicken and H.I.G. Capital in a Bad Light

A recent posting from the Quicken community forum highlights just how bad the relationship has become between Chase and Quicken. The board moderator, “Quicken Natalie” is quick to delete any reference on the forums to the failure of her own organization to address the systematic quality problems that appear to pervasive with their Quicken software. She also deletes any reference to their terrible relationship with Chase Bank. The problems between Quicken and Chase Bank have become notoriously bad over the last three years and shows few signs of any abeyance. In a last fit of their attack-dog strategy, Quicken Kathryn – The Community Administrator, got involved and has now deleted all references to the overall problem, in some vain hope that this posting will just go away, rather than actually solve the problem. This is a good example of where Quicken is today. Poor product, terrible coding and just godawful support.

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Using the new version Quicken r27.42 I get the error message “OL-301-A” when attempting to send for Chase Bill Pay payments.

Member ✭ edited 11:47AM in Errors and Troubleshooting (Windows) Using Quicken r27.42, the error OL-301-A comes up after attempting to send payments through Chase bill pay. The payments actually still go through on the Chase end, but they appear in Quicken as failed.

The “refresh” procedure that is often cited, failed to fix the problem and still comes back with the error on all my accounts

So when I try again and again, I end up getting lots and lots of duplicate transactions at Chase which their support team then have to go through and reverse. What a mess Quicken has created.

Surprisingly, downloading transactions is fine. Sometimes its better not to do the upgrade at all, as it is clearly not tested by Quicken or Chase Bank.

The support team at Quicken treat you like a mental case, until a whole bunch of other people start calling them about the same thing. It is only then that they will accept that the screwed up, again.

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Quicken_Natalie mod  Accepted Answer

Hello All,

Thank you for taking the time to visit the Community and post your issue, although I apologize you’re experiencing difficulties downloading transactions into Quicken.

There is a known issue with Chase Bill Pay returning the OL-301 error that has been reported here.

An Alert has been created and can be found here.

I suggest bookmarking the Alert so that you can be automatically notified of any updates/changes as they’re posted.

Thank you,

Quicken Natalie
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Quicken Francisco Moderator mod

Thank you for reaching out on the community and telling us about your issue. We’re currently seeing in increase in OL-301-A errors. We’re currently also trying to collect more information from our users. If you have a chance please contact Quicken Support Via phone or web chat so we’re able to get logs and get the issue escalated. I’ll also leave our hours down below so you can find a time that works best for you.
Thanks,Quicken Francisco
Quicken Phone Support Current Hours of Operation:Monday through Friday5:00 am to 5:00 pm PDTQuicken Chat Support Current Hours of Operation:Monday through Sunday5:00 am to 5:00 pm PDT
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robertlstein Member ✭✭ edited 12:34AM
Now this is weird. I tried to send payments using direct connect between Quicken and my bank. It has previously worked great.
Today, however, I am getting an OL-301A message “your bank rejected the transaction” message.
But guess what? The payment in fact is showing on the Chase website and is scheduled as it was in Quicken. Quicken shows the “Send” (not SENT) status in its register.

Chase tech support told me that Quicken will no longer support direct connect, which is news to me (I moved my checking to Chase specifically for replacing QBP that’s going away). In any event, Quicken support says talk to Chase, and Chase says talk to Quicken.

This is unacceptable if it’s true that Direct Connect is going away.

(As a test, I have a Bank of the West checking account with Direct Connect, and payments process normally, so this is a Quicken-Chase issue, but who can we talk with that can fix this?)Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  1Like  LOL


dvatani Member ✭
I am having this issue too. The One Step Update dialog now shows “Chase Error Recovery” and now I am getting a different error code of OL-220-A. I’d also gotten the OL301-A code yesterday. I could not get through to Chase to talk with anyone and am extremely dissappointed to learn that Direct Connect is going away.Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  Like  LOL


robertlstein Member ✭✭
The good news is that after I posted, I spoke with Quicken Support. They, of course, have no information that Chase is cancelling Direct Connect and I suspect the Chase support person totally confused QBP wi Direct Connect.

I’m guessing that this in fact is a Chase server side problem.Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  Like  LOL


garacine Member ✭
I’m having the same issue. My transaction was entered about 10 times at Chase before I went and looked. Chase help line said it was a Quicken issue. I’m a 25+ year Quicken user and this is a big issue for me!Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  1Like  LOL


garacine Member ✭My errors are OL-301A and OL 393-A .
I’m pretty dependent on this interaction between Chase and Quicken working, so if anyone has a solution I’m all ears!Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  Like  LOL


robertlstein Member ✭✭
I was disappointed at Chase’s offshore support. Pretty useless, but they promised to escalate. With Citi, all the support/service reps are US based and can access the people who can actually troubleshoot and fix stuff.Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  Like  LOL


TracieK Member ✭
I am having the same issue with not being able to send payments after upgrading to R27.42. I reported the problem through my Quicken software. Any update or fix?Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  Like  LOL


ps56k SuperUser ✭✭✭✭✭ edited 12:24AM
There is another posting on this brand new Chase error…Be aware, that even though Quicken is posting an error –
the uploaded payment transaction may have in fact been received by Chase –
Check your payments via the Chase online website.
I’ve asked the threads be merged.Did this answer the question? Yes · NoQuicken 2020 Deluxe – Subscription – Windows 10
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robertlstein Member ✭✭Yes, @ps56k that was mentioned in my OP. Indeed, this can result in multiple duplicate payments received and processed by Chase, while QFW shows “Send” in the transaction, as if it never got to Chase.Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  1Like  LOL


Joe Member ✭✭I am having the same problem w ol-301 after the update. Receive error that states rejected, but when I go to account at Chase it shows payment went through. I have also noticed that since update, one step update is taking forever to complete as it states WAITING for all accounts and then finally starts to proceed.Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  Like  LOL


Quicken_Natalie Moderator mod Accepted Answer
Hello All,

Thank you for taking the time to visit the Community and post your issue, although I apologize you’re experiencing difficulties downloading transactions into Quicken.

There is a known issue with Chase Bill Pay returning the OL-301 error that has been reported here.

An Alert has been created and can be found here.

I suggest bookmarking the Alert so that you can be automatically notified of any updates/changes as they’re posted.

Thank you,

Quicken Natalie
  Flag  Quote ·  Off Topic  Dislike  Like  LOL


tvmitch Member ✭
I attempted to pay a bill this weekend via Quicken. I received an error on the transaction and it would not send. Turns out, Quicken actually sent the same transaction 5 times to Chase. On my end, it still says not sent. Chase sent 5 checks yesterday for the same transaction! Thankfully I noticed it today and stopped payment. What a nightmare!Did this answer the question? Yes · No Flag  Quote ·  Off Topic  Dislike  Like  LOL

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Michael Rogers

Having never been a member of the 657 crew and still a frequent guest at the Jolly Sailor, Mike likes to travel back to his old stomping grounds once in a while. Rogers has been writing for twenty years about things that really don't matter for such publications as Good Housekeeping and The Radio Times. Married with two dogs and a cat, he will often be found at his desk looking for writing inspiration in the most random places, often in the waste paper basket for something he wrote last week.