diff --git a/crates/pathops/src/edit.rs b/crates/pathops/src/edit.rs
index 94788f8d1..520ff2bd3 100644
--- a/crates/pathops/src/edit.rs
+++ b/crates/pathops/src/edit.rs
@@ -327,7 +327,7 @@ pub const SMOOTH_AUTO_LEVEL: f64 = 50.0;
 /// within a tolerance from 0.1 % of the path's longer side at level 0 to 2.5 % at level 100. A refit
 /// never has more anchor points than the subpath had: a shape whose corners the tolerance can't
 /// round, such as a rectangle, stays as it is. Closed subpaths stay closed, with no kink left where
-/// they start, and open ones keep their end points. A level outside 0..=100 counts as the nearer end, and one that is not a number as
+/// they start unless rounding it would pass the tolerance, and open ones keep their end points. A level outside 0..=100 counts as the nearer end, and one that is not a number as
 /// [`SMOOTH_AUTO_LEVEL`].
 pub fn smooth_level(path: &PathData, level: f64) -> PathData {
     let level = if level.is_finite() { level.clamp(0.0, 100.0) } else { SMOOTH_AUTO_LEVEL };
@@ -338,7 +338,7 @@ pub fn smooth_level(path: &PathData, level: f64) -> PathData {
     let opts = SimplifyOptions { tolerance: size * (0.001 + 0.024 * level / 100.0), corner_angle_deg: SMOOTH_CORNER_DEG, straight_lines: false };
     let smoothed = |sp: &SubPath| {
         let Some(mut fit) = simplify_subpath(sp, &opts).filter(|f| f != sp) else { return sp.clone() };
-        smooth_seam(&mut fit);
+        smooth_seam(&mut fit, sp, opts.tolerance);
         fit
     };
     PathData::new(path.subpaths.iter().map(smoothed).collect())
@@ -349,18 +349,65 @@ const SMOOTH_CORNER_DEG: f64 = 179.0;
 
 /// A closed subpath's refit leaves its start anchor with the tangents of the original segments on
 /// either side of it, a kink when the path had one there: turn it into a smooth anchor with the same
-/// handle lengths, unless the path turns back there.
-fn smooth_seam(sp: &mut SubPath) {
+/// handle lengths, unless the path turns back there or the rounded path would stray from `original`
+/// by more than `tol` (or than the refit already does).
+fn smooth_seam(sp: &mut SubPath, original: &SubPath, tol: f64) {
     if !sp.closed {
         return;
     }
-    let Some(a) = sp.anchors.first_mut() else { return };
+    let Some(a) = sp.anchors.first() else { return };
     let (Some(i), Some(o)) = (crate::fit::unit(a.p - a.h_in), crate::fit::unit(a.h_out - a.p)) else { return };
     if i.dot(o) < SMOOTH_CORNER_DEG.to_radians().cos() {
         return;
     }
     let Some(dir) = crate::fit::unit(i + o) else { return };
-    *a = Anchor::with_handles(a.p, a.p - dir * a.h_in.distance(a.p), a.p + dir * a.h_out.distance(a.p));
+    let mut rounded = sp.clone();
+    if let Some(r) = rounded.anchors.first_mut() {
+        *r = Anchor::with_handles(a.p, a.p - dir * a.h_in.distance(a.p), a.p + dir * a.h_out.distance(a.p));
+    }
+    if seam_error(original, sp, &rounded, tol) <= tol.max(seam_error(original, sp, sp, tol)) {
+        *sp = rounded;
+    }
+}
+
+/// How far the segments on either side of the start anchor of `fit` (a refit of the closed
+/// `original` whose other segments match `before`) are from `original`, both ways: the largest
+/// distance from those segments to `original`, and from the parts of `original` that `before`'s
+/// segments there cover (within `tol`) to `fit`.
+fn seam_error(original: &SubPath, before: &SubPath, fit: &SubPath, tol: f64) -> f64 {
+    use kurbo::ParamCurveNearest;
+    let n = fit.segment_count();
+    if n == 0 || before.segment_count() != n || original.segment_count() == 0 {
+        return f64::INFINITY;
+    }
+    let is_seam = |j: usize| j == 0 || j + 1 == n;
+    let dist = |q: Point, sp: &SubPath, seam: bool| {
+        (0..sp.segment_count())
+            .filter(|&j| is_seam(j) == seam)
+            .map(|j| sp.segment(j).nearest(q, 1e-9).distance_sq)
+            .fold(f64::INFINITY, f64::min)
+            .sqrt()
+    };
+    let samples = |sp: &SubPath, seam_only: bool| {
+        let mut pts = Vec::new();
+        for j in (0..sp.segment_count()).filter(|&j| !seam_only || is_seam(j)) {
+            let c = sp.segment(j);
+            let m = ((c.arclen(1e-6) / (tol.max(1e-6) * 0.5)).ceil() as usize).clamp(4, 256);
+            sample(&c, m, &mut pts, true);
+        }
+        pts
+    };
+    let all = |q: Point| dist(q, original, true).min(dist(q, original, false));
+    let forward = samples(fit, true).into_iter().map(all).fold(0.0, f64::max);
+    let back = samples(original, false)
+        .into_iter()
+        .filter(|&q| dist(q, before, true) <= tol)
+        .map(|q| {
+            let d = dist(q, fit, true);
+            if d > tol { d.min(dist(q, fit, false)) } else { d }
+        })
+        .fold(0.0, f64::max);
+    forward.max(back)
 }
 
 /// Remove anchors that can be deleted without changing the shape by more than `tolerance`
diff --git a/crates/pathops/tests/it/ops.rs b/crates/pathops/tests/it/ops.rs
index 9feaa79a8..c3184a9fc 100644
--- a/crates/pathops/tests/it/ops.rs
+++ b/crates/pathops/tests/it/ops.rs
@@ -445,6 +445,52 @@ fn smooth_level_keeps_corners_it_cannot_round_and_curves_polygons() {
     assert_eq!(smooth_level(&polygon, 0.0), polygon, "0.1 pt is less than the sagitta");
 }
 
+/// The largest distance from a point of `a` to `b` (sampled on `a`, exact on `b`).
+fn one_way_distance(a: &PathData, b: &PathData) -> f64 {
+    use kurbo::ParamCurveNearest;
+    let mut worst = 0.0_f64;
+    for sa in &a.subpaths {
+        for i in 0..sa.segment_count() {
+            let c = sa.segment(i);
+            for k in 0..=64 {
+                let q = c.eval(f64::from(k) / 64.0);
+                let d = b
+                    .subpaths
+                    .iter()
+                    .flat_map(|sb| (0..sb.segment_count()).map(move |j| sb.segment(j).nearest(q, 1e-9).distance_sq))
+                    .fold(f64::INFINITY, f64::min);
+                worst = worst.max(d.sqrt());
+            }
+        }
+    }
+    worst
+}
+
+/// Object › Path › Smooth at level 0 keeps a closed path within 0.1 % of its longer side, a sharp
+/// corner where the path starts included (a drop with a 90° tip at its first anchor).
+#[test]
+fn smooth_level_0_keeps_a_closed_paths_start_corner_within_tolerance() {
+    let n = 24;
+    let step = 1.5 * PI / f64::from(n);
+    let at = |t: f64| {
+        let (r, dr) = (100.0 * (2.0 * t / 3.0).sin(), 200.0 / 3.0 * (2.0 * t / 3.0).cos());
+        (Point::new(r * t.cos(), r * t.sin()), kurbo::Vec2::new(dr * t.cos() - r * t.sin(), dr * t.sin() + r * t.cos()))
+    };
+    let anchors = (0..n)
+        .map(|i| {
+            let (p, d_out) = at(f64::from(i) * step);
+            let d_in = if i == 0 { at(1.5 * PI).1 } else { d_out };
+            vectorcraft_geom::Anchor::with_handles(p, p - d_in * (step / 3.0), p + d_out * (step / 3.0))
+        })
+        .collect();
+    let p = PathData::single(SubPath::new(anchors, true));
+    let b = p.bounds().unwrap();
+    let limit = 0.001 * b.width().max(b.height());
+    let s = smooth_level(&p, 0.0);
+    let moved = one_way_distance(&p, &s).max(one_way_distance(&s, &p));
+    assert!(moved <= limit, "level 0 moved the path by {moved} pt, more than {limit} pt: {:?}", s.subpaths[0].anchors[0]);
+}
+
 #[test]
 fn remove_redundant_collinear_and_curve() {
     let p = PathData::single(SubPath::polyline(