diff --git a/lib/web_ui/lib/src/engine/recording_canvas.dart b/lib/web_ui/lib/src/engine/recording_canvas.dart
index 021ed6262e2bf..2322466e48a07 100644
--- a/lib/web_ui/lib/src/engine/recording_canvas.dart
+++ b/lib/web_ui/lib/src/engine/recording_canvas.dart
@@ -7,6 +7,9 @@ part of engine;
 /// Enable this to print every command applied by a canvas.
 const bool _debugDumpPaintCommands = false;
 
+// Similar to [Offset.distance]
+double _getDistance(double x, double y) => math.sqrt(x * x + y * y);
+
 /// Records canvas commands to be applied to a [EngineCanvas].
 ///
 /// See [Canvas] for docs for these methods.
@@ -228,12 +231,31 @@ class RecordingCanvas {
   }
 
   void drawDRRect(ui.RRect outer, ui.RRect inner, ui.Paint paint) {
-    // If inner rect is not contained inside outer, flutter engine skips
-    // painting rectangle.
-    if (!(outer.contains(ui.Offset(inner.left, inner.top)) &&
-        outer.contains(ui.Offset(inner.right, inner.bottom)))) {
-      return;
+    // Ensure inner is fully contained within outer, by comparing its
+    // defining points (including its border radius)
+    ui.Rect innerRect = inner.outerRect;
+    if (outer.outerRect.intersect(innerRect) != innerRect) {
+      return; // inner is not fully contained within outer
+    }
+
+    // Compare radius "length" of the rectangles that are going to be actually drawn
+    final ui.RRect scaledOuter = outer.scaleRadii();
+    final ui.RRect scaledInner = inner.scaleRadii();
+
+    final double outerTl = _getDistance(scaledOuter.tlRadiusX, scaledOuter.tlRadiusY);
+    final double outerTr = _getDistance(scaledOuter.trRadiusX, scaledOuter.trRadiusY);
+    final double outerBl = _getDistance(scaledOuter.blRadiusX, scaledOuter.blRadiusY);
+    final double outerBr = _getDistance(scaledOuter.brRadiusX, scaledOuter.brRadiusY);
+
+    final double innerTl = _getDistance(scaledInner.tlRadiusX, scaledInner.tlRadiusY);
+    final double innerTr = _getDistance(scaledInner.trRadiusX, scaledInner.trRadiusY);
+    final double innerBl = _getDistance(scaledInner.blRadiusX, scaledInner.blRadiusY);
+    final double innerBr = _getDistance(scaledInner.brRadiusX, scaledInner.brRadiusY);
+
+    if (innerTl >= outerTl || innerTr >= outerTr || innerBl >= outerBl || innerBr >= outerBr) {
+      return; // Some inner radius is overlapping some outer radius
     }
+
     _hasArbitraryPaint = true;
     _didDraw = true;
     final double strokeWidth =
diff --git a/lib/web_ui/test/engine/recording_canvas_test.dart b/lib/web_ui/test/engine/recording_canvas_test.dart
new file mode 100644
index 0000000000000..d8f1963e59aa6
--- /dev/null
+++ b/lib/web_ui/test/engine/recording_canvas_test.dart
@@ -0,0 +1,60 @@
+// Copyright 2013 The Flutter Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+import 'package:ui/ui.dart';
+import 'package:ui/src/engine.dart';
+import 'package:test/test.dart';
+
+import '../mock_engine_canvas.dart';
+
+void main() {
+
+  RecordingCanvas underTest;
+  MockEngineCanvas mockCanvas;
+
+  setUp(() {
+    underTest = RecordingCanvas(Rect.largest);
+    mockCanvas = MockEngineCanvas();
+  });
+
+  group('drawDRRect', () {
+    final RRect rrect = RRect.fromLTRBR(10, 10, 50, 50, Radius.circular(3));
+    final Paint somePaint = Paint()..color = const Color(0xFFFF0000);
+
+    test('Happy case', () {
+      underTest.drawDRRect(rrect, rrect.deflate(1), somePaint);
+      underTest.apply(mockCanvas);
+      // Expect drawDRRect to be called
+      expect(mockCanvas.methodCallLog.length, equals(1));
+      MockCanvasCall mockCall = mockCanvas.methodCallLog[0];
+      expect(mockCall.methodName, equals('drawDRRect'));
+      expect(mockCall.arguments, equals({
+          'outer': rrect,
+          'inner': rrect.deflate(1),
+          'paint': somePaint.webOnlyPaintData,
+        }));
+    });
+
+    test('Inner RRect > Outer RRect', () {
+      underTest.drawDRRect(rrect, rrect.inflate(1), somePaint);
+      underTest.apply(mockCanvas);
+      // Expect nothing to be called
+      expect(mockCanvas.methodCallLog.length, equals(0));
+    });
+
+    test('Inner RRect not completely inside Outer RRect', () {
+      underTest.drawDRRect(rrect, rrect.deflate(1).shift(const Offset(0.0, 10)), somePaint);
+      underTest.apply(mockCanvas);
+      // Expect nothing to be called
+      expect(mockCanvas.methodCallLog.length, equals(0));
+    });
+
+    test('Inner RRect same as Outer RRect', () {
+      underTest.drawDRRect(rrect, rrect, somePaint);
+      underTest.apply(mockCanvas);
+      // Expect nothing to be called
+      expect(mockCanvas.methodCallLog.length, equals(0));
+    });
+  });
+}