When you fire up Quicken Classic for Windows, you get a little splash screen saying that they play well with Fidelity. This is a lie.
I have used Quicken ever since Microsoft Money was discontinued in 2009. I have parked my money in various Fidelity accounts over the years. They have never played well together.
Today, I have nine (9) Fidelity accounts. Downloading works great - until it doesn't, and once again I get the dreaded OL-220A. The only fix is to deactivate and reactivate all nine accounts. Lately this Happens. Every. Time. Only to Fidelity, though—itty bitty banks connect no problem.
THIS IS NOT, NOT, NOT A FIDELITY ISSUE!! This is Quicken not willing to fix a recurring problem with the largest brokerage on the planet, one they consider a "partner."
Am I unique? Heck no - see
That string is closed. Let's open another so that the folks at Quicken are aware of this continuing pain.