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Nearly 2 years later, I finally found the answer thanks to Gemini...
Go to Window > Preferences > Editors > SQL Editor > SQL Processing and set "Error handling" to "Stop + rollback" instead of "Ignore"

Apparently if you want error pop ups, this is necessary. Stupid if you ask me, because I'd like error pop-ups without rollbacking, but well...

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Answer selected by wheinen
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