Yes, the spy getting the gates opened has many historical precedents. The spy recruits others within a settlement who for political, financial, or self preservation reasons secure the gatehouse. The odd part is still that all gates are open, but we won't go there...
And even if the men at the pots were not somehow disabled, they would not be prepared for the assault, so at best it would take them time to stoke the fires, heat the oil, and be ready to pour. They would not have sufficient time when the gates were *already open*.
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