Quicken for Mac Premier 2019-MacOS 10.12.6. Recently I have to enter my password each time I do an

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repeated sign in requests when updating
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You can try this:
1) Quit Quicken
2) Open Keychain Access from the Applications > Utilities folder
3) find and delete all "quicken" entries
4) quit Keychain Access
5) launch Quicken
You will have to enter each password one more time. Make sure you check the box to save in your keychain.Quicken Mac Subscription; Quicken Mac user since the early 90s0
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