Fidelity Online Balance - includes investments values - can't reconcile

@Brad L Vandermoon I assume you're talking here about a brokerage (e.g. non-retirement) account, right? The "Dividend Income Tax-Free" is not something that is sent by the financial institution. When you hold a tax-free security in a brokerage account, you need to set the security in Quicken to be tax-exempt. Here's an example:

With that checkbox set, dividend income from that security will be tax-free and will not appear as taxable income in Quicken reports.

Whether a reinvested dividend gets downloaded as two transactions — a cash dividend followed by a purchase of shares — or as a single reinvested dividend transaction is entirely up to how the financial institution reports it; from Quicken's standpoint, it does not matter which way is used.

The only potential problem I see in what you wrote is that you said the dividend payments "come in as a payment transaction". Do you mean they come in as Type=Dividend transactions which show the security and increase the cash balance? If so, that's exactly as it should be. Or do you mean they come in as a Type=Payment/Deposit transaction, whithout being associated with the security? That would be wrong.

@Brad L Vandermoon So is the transaction which downloads Type=Payment/Deposit? Just want to make sure I'm understanding correctly. If so, that has to be an error on the Fidelity end; if Fidelity were reporting it as a Dividend and specifying the security correctly, that's the way it would import into Quicken. (The only time it wouldn't is if the security is the core money market fund for the account, because those do get recorded as cash — but the two ticker symbols you mentioned are not money market funds.)