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EU Regulation 261/2004 mentions "extraordinary circumstances" several times as a condition under which airlines are not obligated to pay out compensation:

(12) The trouble and inconvenience to passengers caused by cancellation of flights should also be reduced. This should be achieved by inducing carriers to inform passengers of cancellations before the scheduled time of departure and in addition to offer them reasonable re-routing, so that the passengers can make other arrangements. Air carriers should compensate passengers if they fail to do this, except when the cancellation occurs in extraordinary circumstances which could not have been avoided even if all reasonable measures had been taken.

(14) As under the Montreal Convention, obligations on operating air carriers should be limited or excluded in cases where an event has been caused by extraordinary circumstances which could not have been avoided even if all reasonable measures had been taken. Such circumstances may, in particular, occur in cases of political instability, meteorological conditions incompatible with the operation of the flight concerned, security risks, unexpected flight safety shortcomings and strikes that affect the operation of an operating air carrier.

(15) Extraordinary circumstances should be deemed to exist where the impact of an air traffic management decision in relation to a particular aircraft on a particular day gives rise to a long delay, an overnight delay, or the cancellation of one or more flights by that aircraft, even though all reasonable measures had been taken by the air carrier concerned to avoid the delays or cancellations.

  1. An operating air carrier shall not be obliged to pay compensation in accordance with Article 7, if it can prove that the cancellation is caused by extraordinary circumstances which could not have been avoided even if all reasonable measures had been taken.

How can one know if their particular reason for delay/cancellation counts as "extraordinary circumstances"? Is there a list of all court cases related to EU 261/2004 that would help travelers evaluate their particular scenario?

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Is there a list of all court cases related to EU 261/2004 that would help travelers evaluate their particular scenario?

Yes, at least of all court cases in the EU court system. Cases in national courts are not included. It is found by selecting "document information" on the page you linked to in the question. there is a long list under the heading "affected by case." There is also a summary of CJEU judgements on the official EU website.

But this isn't necessarily going to be particularly helpful.

How can one know if their particular reason for delay/cancellation counts as "extraordinary circumstances"?

You can't, really, unless the circumstances of your delay match those in one of the cases very closely. But there are some general principles that are outlined fairly well in an answer to a recent question, based on a pretty good blog post that appears to be from a company that handles these claims in return for a percentage of the payment (I haven't looked very closely). I know nothing about the company, but the post is very clear and thorough.

The general points are these:

  1. You are entitled to receive evidence of the circumstances that they are claiming were extraordinary and the steps they have taken to deal with them. The airline's own statement of the circumstances is not sufficient by itself.

  2. Circumstances are extraordinary if an event "is not inherent in the normal exercise of the activity of the air carrier and is beyond the actual control of that carrier on account of its nature or origin."

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