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One 'problem' account is Chase. Another bank account is OK
The other problem account is Schwab.

I currently use the macOS variant of Quicken. It's been a few years since I've used the Windows variant.

What you originally described sounds like a timing problem with Quicken aggregation server contacting the Chase and Schwab Express Web Connect servers.

The Quicken Community has a number of discussions regarding connection and download problems from both financial institutions. You might want to visit for more information.
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