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This is a recurring problem which I have also encountered with other extensions. The download step isn't actually skipped, it just downloads a zero-length file. The file exists so SQL Developer tries to load it on restart but fails. Repeating the exercise just downloads a new version of the empty file.
It is another symptom of Oracle's generally flaky download servers, and I have never solved it satisfactorily.
There is workaround which involves obtaining the file by other means and then selecting the 'Install from local file' on the update dialog box.
Getting hold of the file by other means is a whole other problem...
To do Install from Local File, you need this patch file:
The hard way is to copy (actually, type out) the link from the Oracle SQL Developer Update Center in Check for Updates :
into your web browser, then search through the resulting xml file for above-mentioned link to the patch file.
SQL Developer Team