This matches nothing:
Query replace regexp (default \.org.+ → ): \.org.+$ →
The same without '$' matches incompletely:
I'd like to be able to match
\.org and all that follows.
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\.org.+$ works for me, starting from
Try starting Emacs using
emacs -Q (no init file). Do you see the same thing? If not, bisect your init file to find the culprit.
(Maybe pay attention too to what whitespace you're trying to match. Your question is underspecified. All we have to go on is your screenshot - we have no idea what whitespace chars you're trying to match, etc.)