With Lee’s and Longstreet’s rather vague advice in hand, Stuart turned to his most trusted scout, John Singleton Mosby, for information on the best route to take into Pennsylvania. Mosby, who would later find fame as the commanding colonel of an effective independent cavalry unit in northern Virginia, Mosby’s Rangers, was still serving on Stuart’s personal staff. He rode into headquarters on June 23 with word that Stuart could pass safely around the rear of Hooker’s widely dispersed army in western Maryland en route to Pennsylvania. Hooker, said Mosby, was lying idle along a 25-mile-long line from Leesburg, Va., to Thoroughfare Gap, just west of Haymarket, and the Federal line was stretched so thin that Stuart could simply ride through it. It was a dangerously overoptimistic assessment of the military situation, based on the assumption that the Federals would simply sit still and wait for events to overtake them. But Stuart trusted Mosby implicitly and was, at any rate, always ready to accept information that conformed to his own expectations.

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Stuart liked the plan so well that he committed it to paper and showed it to the commanders of his two brigades, Brig. Gens. Fitzhugh Lee and Wade Hampton. He then detailed his strategy to Lee and Longstreet. Stuart’s plan called for him to pass through Glasscock Gap, then head northeast, crossing the Potomac at Seneca Ford and joining Ewell in Pennsylvania. Stuart fully expected his cavalry to pass to the rear of the Union army, severing communications between Hooker and his own cavalry commander, Brig. Gen. Alfred Pleasonton, destroying transportation for the Union army, and taking pressure off Lee by creating a diversion and slowing down Hooker’s movements. Once in Maryland, Stuart would wreck the C&O Canal and destroy railroad communications with Washington.

Stuart went to army headquarters at Berryville to await Lee’s approval of his plan. He was sleeping out in the open under a poncho when Lee’s response arrived. Stuart’s adjutant, Major Henry McClellan, opened the letter (clearly marked confidential) and woke Stuart to show him the message. Lee had written: If General Hooker’s army remains inactive, you can leave two brigades to watch him, and withdraw with the three others, but should he not appear to be moving northward, I think you had better withdraw this side of the mountain tomorrow night, cross at Shepherdstown next day and move to Fredericktown [Frederick]. You will, however, be able to judge whether you can pass around their army without hindrance, doing them all the damage you can, and cross the river east of the mountains. In either case, after crossing the river, you must move on and feel the right of Ewell’s troops, collecting information, provisions, etc. Give instructions to the commander of the brigades left behind to watch the flank and rear of the army and (in event of the enemy leaving their front) retire from the mountains west of the Shenandoah, leaving sufficient pickets to guard the passes, and bringing everything clean along the valley, closing upon the rear of the army.

The second letter from Lee was ambiguous and somewhat illogical, especially when considering his first letter. Initially, Lee had told Stuart he was concerned that Hooker might steal a march on us and get across the Potomac before we are aware. His first set of instructions ordered Stuart to link up with Ewell’s right and guard his flank, while also collect[ing] all the supplies you can for the use of the army. That in itself was a rather contradictory order, especially for a cavalryman famous for his independent raiding sorties.

The second letter told Stuart he could move if General Hooker’s army remains inactive [emphasis added] and simultaneously advised Stuart to enter Maryland west of the Blue Ridge Mountains or pass around the Federals east of the mountains and then feel the right of Ewell’s troops. Besides giving Stuart two dramatically different routes to take, Lee had softened the stipulation that the cavalry link up with Ewell and guard his flank. And his remark that Stuart should do as much damage as possible seemed to be directed more at a raiding party than a flank-guarding detail. Lee also gave Stuart the latitude to judge whether he could pass around their army without hindrance. It would be up to Stuart to decide what constituted a true hindrance, as opposed to a momentary complication.

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