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The natural generalization of your "straightest-possible" constraint is a curvature-constrained path. I know this is not what you asked, but I wanted to mention that even finding a path with maximum curvature 1 inside a convex polygon is already difficult. This was studied by Agarwal et al. in a paper, "Curvature-Constrained Shortest Paths in a Convex Polygon," (SIAM Journal on Computing, Volume 31, Issue 6, 2002) Here is one of their figures, which hints at why it is difficult to find a path from between initial $I$ to and final $T$ F$positions/orientations: Returning to the question (or questions) you did ask, I think looking at the paper "Polygonal path simplification with angle constraints," by Chen et al. (Computational Geometry, Volume 32, Issue 3, November 2005, Pages 173-187), might help. They explicitly consider the "tunnel" version of your revised question, phrased in terms of an error tolerance$\epsilon$. Perhaps most usefully for your purposes, they describe all the related work in this domain, which has considered many variations. Usually those variations start with a path$P$, and then try to find another path (a "simplification") with certain properties: (1) The min-# problem: Find a path that remains within$\epsilon$of$P$but has the fewest segments; (2) The min-$\epsilon$problem: Given a fixed number$m$of segments, find a path using no more than$m$segments that minimizes$\epsilon$. This specific paper solves the min-# problem with the addition of angular constraints, which seems close to your initial formulation (as clarified in the comments). Edit. Here is a preliminary version of the "Simplification" paper: simplification.pdf. 2 Added private copy of prelim version of paper. The natural generalization of your "straightest-possible" constraint is a curvature-constrained path. I know this is not what you asked, but I wanted to mention that even finding a path with maximum curvature 1 inside a convex polygon is already difficult. This was studied by Agarwal et al. in a paper, "Curvature-Constrained Shortest Paths in a Convex Polygon," (SIAM Journal on Computing, Volume 31, Issue 6, 2002) Here is one of their figures, which hints at why it is difficult to find a path from$I$to$T$positions/orientations: Returning to the question (or questions) you did ask, I think looking at the paper "Polygonal path simplification with angle constraints," by Chen et al. (Computational Geometry, Volume 32, Issue 3, November 2005, Pages 173-187), might help. They explicitly consider the "tunnel" version of your revised question, phrased in terms of an error tolerance$\epsilon$. Perhaps most usefully for your purposes, they describe all the related work in this domain, which has considered many variations. Usually those variations start with a path$P$, and then try to find another path (a "simplification") with certain properties: (1) The min-# problem: Find a path that remains within$\epsilon$of$P$but has the fewest segments; (2) The min-$\epsilon$problem: Given a fixed number$m$of segments, find a path using no more than$m$segments that minimizes$\epsilon$. This specific paper solves the min-# problem with the addition of angular constraints, which seems close to your initial formulation (as clarified in the comments). Edit. Here is a preliminary version of the "Simplification" paper: simplification.pdf. 1 The natural generalization of your "straightest-possible" constraint is a curvature-constrained path. I know this is not what you asked, but I wanted to mention that even finding a path with maximum curvature 1 inside a convex polygon is already difficult. This was studied by Agarwal et al. in a paper, "Curvature-Constrained Shortest Paths in a Convex Polygon," (SIAM Journal on Computing, Volume 31, Issue 6, 2002) Here is one of their figures, which hints at why it is difficult to find a path from$I$to$T$positions/orientations: Returning to the question (or questions) you did ask, I think looking at the paper "Polygonal path simplification with angle constraints," by Chen et al. (Computational Geometry, Volume 32, Issue 3, November 2005, Pages 173-187), might help. They explicitly consider the "tunnel" version of your revised question, phrased in terms of an error tolerance$\epsilon$. Perhaps most usefully for your purposes, they describe all the related work in this domain, which has considered many variations. Usually those variations start with a path$P$, and then try to find another path (a "simplification") with certain properties: (1) The min-# problem: Find a path that remains within$\epsilon$of$P$but has the fewest segments; (2) The min-$\epsilon$problem: Given a fixed number$m$of segments, find a path using no more than$m$segments that minimizes$\epsilon\$. This specific paper solves the min-# problem with the addition of angular constraints, which seems close to your initial formulation (as clarified in the comments).