Do you have any errors when deleting such Items from Recycle bin in the browser console or in the error logs.
Please remove all the files under <your project>\App_Data\Sitefinity\Logs\... , r
eproduce the case and check or provide the file/s generated in the above mentioned folder.
Do you have this behaviour with that particular Content type/Content Item only?
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and vote to affect the priority of the items