The mistakes riders make when first attempting counter-canter are predictable and understanding them in advance significantly reduces the frustration that comes from repeatedly producing swaps, breaks, and resistance rather than genuine counter-canter. The most common mistake is asking for too much curve too soon. Riders who have read about counter-canter and understand the concept often go directly to a full circle or a sharp corner without building through the progressive curve stages that allow the horse to develop the balance for the exercise. The result is a horse that breaks every time the corner is reached, which teaches the horse to associate corners with transitions rather than with counter-canter maintenance. The second common mistake is using the wrong leg aids — specifically, putting the inside leg at the cinch for the direction of travel rather than for the lead being maintained. In counter-canter going right on the left lead, the left leg should be at the cinch (the lead-side leg) and the right leg behind. A rider who habitually positions legs for the direction of travel rather than the lead will inadvertently signal a lead change every time the counter-canter is attempted. A third mistake is allowing the horse to drift to the inside during counter-canter — letting the horse cut the corners and reduce the curve by drifting inward rather than holding the line being ridden. A horse that drifts inside during counter-canter is reducing the demand of the exercise to a manageable level, which means the exercise is not developing the balance it is intended to develop. Maintaining the line — keeping the horse on the actual path being ridden — is essential for the exercise to be productive. Finally, drilling counter-canter — asking for many consecutive counter-canter circles or extended counter-canter sessions — before the horse has the collection to sustain it produces tired, tense horses that learn to resist the exercise rather than develop through it. Short, successful counter-canter sessions with generous transitions back to correct-lead canter are more productive than extended sessions that exhaust the horse before it can find the balance that makes the exercise feel achievable.
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Watch: Common Mistakes Riders Make When First Attempting Counter-Canter

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Clinton Anderson: Counter Cantering — Common Mistakes Riders Make When First Attempting Counter-Canter
Downunder Horsemanship