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Haha yes I encountered this exact issue too. How do we @ apple to get this fixed. haha.
I didn't know if others would have this issue so I didn't think twice about it, but will update the GitHub instructions since we're not alone. Thank you @rworne !!
Found one possible reason for it:
Do not use your Apple watch to confirm the password dialog. Click "use password" instead and type it in. Now it will remain checked.
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