Same as the title:
Can you lose money in Vanguard money market settlement fund?
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Possible but very unlikely. Money market funds invest in high grade liquid assets and the primary goal is not to lose money. I have not been able to find an example of a Vanguard money market fund ever "breaking the buck" and having the value of a share go below a dollar. It is possible that this could happen in the event of a large scale financial collapse, but even then I would call it possible rather than likely.