When using CiviRules, what happens if two rules match a single trigger? Rule one says "if group X is added, filter matches X location, then send e-mail X." Rule two says "if group X is added, filter matches Y location, then send e-mail Y." Do both rules trigger? Does it dump after triggering the first applicable reached rule, even if the filter doesn't match?

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It should do both. I have two rules with the same trigger - membership changed with different conditions- (a) membership status is one of the ones I consider active and (b) membership status is one that I do not consider active. Both are working. But I'd still do some tests on your precise requirement to see that it does what you want.

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