diff --git a/Userland/Libraries/LibGfx/Painter.cpp b/Userland/Libraries/LibGfx/Painter.cpp
index 7f28634f98..cec2980fe0 100644
--- a/Userland/Libraries/LibGfx/Painter.cpp
+++ b/Userland/Libraries/LibGfx/Painter.cpp
@@ -2323,10 +2323,12 @@ void Painter::for_each_line_segment_on_elliptical_arc(FloatPoint p1, FloatPoint
     auto start = p1;
     auto end = p2;
 
+    bool start_swapped = false;
     if (theta_delta < 0) {
         swap(start, end);
         theta_1 = theta_1 + theta_delta;
         theta_delta = fabsf(theta_delta);
+        start_swapped = true;
     }
 
     auto relative_start = start - center;
@@ -2351,6 +2353,13 @@ void Painter::for_each_line_segment_on_elliptical_arc(FloatPoint p1, FloatPoint
         p.set_y(original_x * sin_x_axis + original_y * cos_x_axis);
     };
 
+    auto emit_point = [&](auto p0, auto p1) {
+        // NOTE: If we swap the start/end we must swap the emitted points, so correct winding orders can be calculated.
+        if (start_swapped)
+            swap(p0, p1);
+        callback(p0, p1);
+    };
+
     for (float theta = theta_1; theta <= theta_1 + theta_delta; theta += theta_step) {
         float s, c;
         AK::sincos(theta, s, c);
@@ -2358,12 +2367,12 @@ void Painter::for_each_line_segment_on_elliptical_arc(FloatPoint p1, FloatPoint
         next_point.set_y(b * s);
         rotate_point(next_point);
 
-        callback(current_point + center, next_point + center);
+        emit_point(current_point + center, next_point + center);
 
         current_point = next_point;
     }
 
-    callback(current_point + center, end);
+    emit_point(current_point + center, end);
 }
 
 // static