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Recently I had flagged some posts for which the flag was initially declined but just little later the concerned questions were closed or migrated for exactly the reason I had flagged them for. Examples are,
Open source Java/C statistics functions [on hold]
Normality and heteroscedasticity problems in panel data [on hold]
Pseudo R squared for cumulative link function

Not sure if I just got unlucky, if I am flagging too much (though on the other hand the vast majority of my flags is usually accepted) or if this was a system related thing?

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I am moving my guess comment as an answer, as it seems other users shared the same opinion.

I guess it can happen (happened with me a few times).

For example, the first two reviewers or one moderator did not agree with you and declined the raised flag.
But after that, let's suppose another user flagged the same question for the same reason as you did.

I see two possible paths:

  1. Other peer reviewers can have approved the flag (because they understood differently from previous reviewers).

  2. The reviewers who declined your flag in first place, could have changed their minds due to having more people thinking as you did.

Addition to above comment:

Once in a while, discussions come up on grey areas about closing and migrating.

One alternative to surpass this situation consists of leaving comments to the OP asking for clarification or providing guidance.

This strategy requires some time to revisit the comments after some time and if no reply is given by the OP, then the question can be flagged more safely. Some cases it is better to flag the question right away (it depends on individual judgement).


Hint - to increase effectiveness of leaving comments.

Probably, many users already know about this, but I recently (motivated by this thread) discovered the AutoReviewComments* script for customizing standard warnings on SE.

It was designed specially to deal with newcomers who naturally know very little about the site's functioning rules.

*developed by Benjol

I am not using it yet, but looks promising.

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