Here we study the problem of sampling random proper colorings of a bounded degree graph. Let $k$ be the number of colors and let $d$ be the maximum degree. In 1999, Vigoda showed that the Glauber dynamics is rapidly mixing for any $k > \frac{11}{6} d$. It turns out that there is a natural barrier at $\frac{11}{6}$, below which there is no one-step coupling that is contractive, even for the flip dynamics. We use linear programming and duality arguments to guide our construction of a better coupling. We fully characterize the obstructions to going beyond $\frac{11}{6}$. These examples turn out to be quite brittle, and even starting from one, they are likely to break apart before the flip dynamics changes the distance between two neighboring colorings. We use this intuition to design a variable length coupling that shows that the Glauber dynamics is rapidly mixing for any $k\ge \left(\frac{11}{6} - ε_0\right)d$ where $ε_0 \geq 9.4 \cdot 10^{-5}$. This is the first improvement to Vigoda's analysis that holds for general graphs.