With a combined force of 341 men, of which Bailey commanded three companies of 197 soldiers, he and Lt. Col. Major Isaiah Stillman were ordered by Governor John Reynolds to guard the settled areas of the Mississippi and Illinois rivers after receiving reports of Black Hawk moving in to threaten the frontier.
[3] On May 12, while staying at Dixon's Ferry, he and Stillman encountered Brigadier General Samuel Whiteside and Governor Reynolds, having been en route to Black Hawk's camp by way of the village of the Winnebago Prophet.
During the proceedings, fighting broke out when militiamen shot at scouts seen on the hillside, resulting in the death of one of the emissaries and a militia flagbearer, while the other two messengers escaped to report back to Black Hawk.
In an attempt to cover their retreat, 12 militiamen under Captain John Giles Adams fought to the death while holding off their Sauk pursuers on a hill south of the militia camp.
[4][5][6] The presence of Bailey during the battle is unclear, although it is presumed he had some role in directing the 30-mile (48 km) retreat back to rejoin the main force at Dixon's Ferry, as he and Stillman survived to make their report.
[7] Although held responsible for the defeat, it is accepted by many historians that both Bailey and Stillman may have been unfairly blamed for the disastrous battle which was due more to the unclear orders given by Governor John Reynolds, whose actions may have been politically motivated.