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Missing Fidelity HSA Transactions

Mortimer Duke

Simplifi has stopped showing all transactions to my Fidelity HSA after October 3, 2025. Any suggestions?

Also, though it took me some time to figure out what it was doing, Simplifi seems to consolidate multiple transactions from a given payee on a particular day into a single transaction in the Simplifi ledger. Is this Simplifi's doing or how Fidelity sends data across to it? Have others noticed similar phenomena?

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Coach Jon

Hello @Mortimer Duke,

Thank you for reaching out! I am sorry that you are not receiving transactions in your Fidelity HSA account. Can you confirm if the account balance is still updating within Quicken Simplifi? Have you tried the following steps to see if they work to resolve the issue you are seeing?

Navigate to the bank's website, sign in, and then remove Quickens access from the bank's third-party linked apps.
Make all of the accounts with the bank manual by following the steps here.
Once you see the account(s) listed in the Manual Accounts section under Settings > Accounts, go back through the Add Account flow to reconnect to the bank.
If the connection is successful, carefully link the account(s) found to your existing Quicken Simplifi account(s) by following the steps here.

As for your second inquiry, this could very well be how your financial institution sends over data, but I would not be sure myself. Have you verified if the transactions show up the same way on the bank's website? Let us know!

-Coach Jon

Mortimer Duke

Thanks. I'll try removing and readding the account.

As for the second portion, the ledger at Fidelity shows discrete ledger entries for each transaction.

Coach Jon

Hello @Mortimer Duke,

Thank you for the reply! I apologize, but after more research, I have verified that Fidelity HSA Accounts do NOT download transactions. This is due to HIPAA. Users will need to manually enter their Investment Transactions for these particular accounts in Quicken Simplifi.

I am sorry I do not have a better solution.

-Coach Jon

Mortimer Duke

Wow. Fascinating. Thanks.

interesting that transactions prior to October 3 exist,

Mortimer Duke

Things keep getting more interesting.

Within Fidelity's website is a setting that grants or restricts access by third party applications to data on an account by account basis. Access to the HSA is enabled, so I would expect Simplifi to be able to access it.

Upon completing all of the prescribed steps above, the account balance now appears but without any transaction history. Previously, the account type was set to Savings. After being re-added, only types within the Investment category are selectable.

This begs the questions, what is the most appropriate account type for an HSA since none of the available choices (IRA, 401K, Keough, etc) fit very well and why can I not set it to Savings as is once was when Simplifi was reflecting all of the data correctly prior to October 3, 2025?

Lastly, is all of the transactional data lost for good?

SRC54

Yes, in regard to your second point, Fidelity Investment accounts have to be set to investment accounts in Simplifi. Supposedly there is work ongoing to come up with a better solution especially for cash management accounts.

You might be better off with a manual account if you want to keep up with transactions. OTOH, if all you really need is the balance, I would leave it alone. Just my two cents.

Mortimer Duke

I appreciate your input - though it makes me want to understand how I was able to designate the HSA as Savings account before I made matters worse by setting out to fix them. 🤣

SRC54

It happened along about last April 2025. I still have my Cash Management Fidelity account as a savings account, but I don't use it much. I have been waiting for the "fix". The problem with cash management accounts that are used as checking accounts is that:

Simplifi won't allow splits in investments accounts.
Dividends come in as buys and sells.

I clean up the dividends as a simple payment/deposit dividend and delete the extra transaction.

There have been offered some workarounds to get Simplifi to keep this as a bank account, but it has been hit or miss.