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I have created a rollup summary for Account in relation to Opportunity with the filter criteria:

Stage EQUALS Negotiation/Review, Closed Won

The above criteria give perfect results, but when I change them to:

(Stage EQUALS Negotiation/Review) AND (Stage EQUALS Closed Won)

The above criteria yields Null. Why? This result seems incorrect.

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The two criteria you presented are different. The first one tries to find records which Stage field is one of the two options. The second one tries to find records which Stage field is both Negotiation/Review AND Closed Won at the same time, which won't happen.

You can use the second approach if you change the AND connector by OR.

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