diff --git a/jetCheck/src/jetCheck/PropertyFailureImpl.java b/jetCheck/src/jetCheck/PropertyFailureImpl.java
index 47c95e2ae5aa..b6f255b267d3 100644
--- a/jetCheck/src/jetCheck/PropertyFailureImpl.java
+++ b/jetCheck/src/jetCheck/PropertyFailureImpl.java
@@ -76,20 +76,35 @@ class PropertyFailureImpl<T> implements PropertyFailure<T> {
   }
 
   private void shrink() {
-    ShrinkStep step = minimized.data.shrink();
-    while (step != null) {
-      step = findSuccessfulShrink(step);
-      if (step != null) {
-        step = step.onSuccess(minimized.data);
-      }
+    NodeId limit = null;
+    while (true) {
+      ShrinkStep lastSuccessfulShrink = shrinkIteration(limit);
+      if (lastSuccessfulShrink == null) break;
+      limit = lastSuccessfulShrink.getNodeAfter();
     }
   }
 
+  private ShrinkStep shrinkIteration(NodeId limit) {
+    ShrinkStep lastSuccessfulShrink = null;
+    ShrinkStep step = minimized.data.shrink();
+    while (step != null) {
+      step = findSuccessfulShrink(step, limit);
+      if (step != null) {
+        lastSuccessfulShrink = step;
+        step = step.onSuccess(minimized.data);
+      }
+    }
+    return lastSuccessfulShrink;
+  }
+
   @Nullable
-  private ShrinkStep findSuccessfulShrink(ShrinkStep step) {
+  private ShrinkStep findSuccessfulShrink(ShrinkStep step, @Nullable NodeId limit) {
     List<CustomizedNode> combinatorial = new ArrayList<>();
 
     while (step != null) {
+      if (limit != null && limit.number <= step.getNodeAfter().number) {
+        break;
+      }
       StructureNode node = step.apply(minimized.data);
       if (node != null && iteration.session.generatedHashes.add(node.hashCode())) {
         CombinatorialIntCustomizer customizer = new CombinatorialIntCustomizer();
diff --git a/jetCheck/src/jetCheck/RemoveListRange.java b/jetCheck/src/jetCheck/RemoveListRange.java
index 1066a5a197a5..d78c9c804d39 100644
--- a/jetCheck/src/jetCheck/RemoveListRange.java
+++ b/jetCheck/src/jetCheck/RemoveListRange.java
@@ -3,6 +3,7 @@
  */
 package jetCheck;
 
+import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
 
 import java.util.ArrayList;
@@ -70,4 +71,20 @@ class RemoveListRange extends ShrinkStep {
     int newLength = Math.min(length * 2, start - 1);
     return new RemoveListRange(inheritor, start, start - newLength, newLength);
   }
+
+  @NotNull
+  @Override
+  NodeId getNodeAfter() {
+    return node.id;
+  }
+
+  @Override
+  public String toString() {
+    return "RemoveListRange{" +
+           "last=" + lastSuccessfulRemove +
+           ", start=" + start +
+           ", length=" + length +
+           ", node=" + node.id + ": " + node +
+           '}';
+  }
 }
diff --git a/jetCheck/src/jetCheck/ShrinkStep.java b/jetCheck/src/jetCheck/ShrinkStep.java
index 2d6bc4becdd0..63c035621e6b 100644
--- a/jetCheck/src/jetCheck/ShrinkStep.java
+++ b/jetCheck/src/jetCheck/ShrinkStep.java
@@ -23,6 +23,9 @@ abstract class ShrinkStep {
   @Nullable
   abstract ShrinkStep onFailure();
 
+  @NotNull 
+  abstract NodeId getNodeAfter();
+
   static ShrinkStep create(@NotNull NodeId replaced,
                            @NotNull StructureElement replacement,
                            @Nullable Function<StructureNode, ShrinkStep> onSuccess,
@@ -45,6 +48,17 @@ abstract class ShrinkStep {
       ShrinkStep onFailure() {
         return onFailure == null ? null : onFailure.get();
       }
+
+      @NotNull
+      @Override
+      NodeId getNodeAfter() {
+        return replacement.id;
+      }
+
+      @Override
+      public String toString() {
+        return "replace " + replaced + " with " + replacement;
+      }
     };
   }
 }
diff --git a/jetCheck/src/jetCheck/StructureNode.java b/jetCheck/src/jetCheck/StructureNode.java
index af04c1ec82a0..c8ac7807a1f4 100644
--- a/jetCheck/src/jetCheck/StructureNode.java
+++ b/jetCheck/src/jetCheck/StructureNode.java
@@ -110,6 +110,17 @@ class StructureNode extends StructureElement {
       ShrinkStep onFailure() {
         return wrapChildShrink(index, step.onFailure());
       }
+
+      @NotNull
+      @Override
+      NodeId getNodeAfter() {
+        return step.getNodeAfter();
+      }
+
+      @Override
+      public String toString() {
+        return "-" + step.toString();
+      }
     };
   }
 
diff --git a/jetCheck/test/jetCheck/GeneratorTest.java b/jetCheck/test/jetCheck/GeneratorTest.java
index 85bbcf40c1f9..efb64763b92f 100644
--- a/jetCheck/test/jetCheck/GeneratorTest.java
+++ b/jetCheck/test/jetCheck/GeneratorTest.java
@@ -20,7 +20,7 @@ public class GeneratorTest extends PropertyCheckerTestCase {
   public void testListSumMod() {
     checkFalsified(nonEmptyLists(integers()),
                    l -> l.stream().mapToInt(Integer::intValue).sum() % 10 != 0,
-                   181);
+                   390);
   }
 
   public void testListContainsDivisible() {
@@ -44,7 +44,7 @@ public class GeneratorTest extends PropertyCheckerTestCase {
   public void testIsSorted() {
     PropertyFailure<List<Integer>> failure = checkFalsified(nonEmptyLists(integers()),
                                                             l -> l.stream().sorted().collect(Collectors.toList()).equals(l),
-                                                            20);
+                                                            22);
     List<Integer> value = failure.getMinimalCounterexample().getExampleValue();
     assertEquals(2, value.size());
     assertTrue(value.toString(), value.stream().allMatch(i -> Math.abs(i) < 2));
@@ -57,7 +57,7 @@ public class GeneratorTest extends PropertyCheckerTestCase {
   public void testSortedDoublesNonDescending() {
     PropertyFailure<List<Double>> failure = checkFalsified(listsOf(doubles()),
                                                            l -> isSorted(l.stream().sorted().collect(Collectors.toList())),
-                                                           35);
+                                                           41);
     assertEquals(2, failure.getMinimalCounterexample().getExampleValue().size());
   }
 
diff --git a/jetCheck/test/jetCheck/ShrinkTest.java b/jetCheck/test/jetCheck/ShrinkTest.java
index e87884a6d191..b14ca3a2a5cc 100644
--- a/jetCheck/test/jetCheck/ShrinkTest.java
+++ b/jetCheck/test/jetCheck/ShrinkTest.java
@@ -3,7 +3,11 @@
  */
 package jetCheck;
 
+import java.util.Arrays;
+import java.util.HashSet;
 import java.util.List;
+import java.util.Set;
+import java.util.function.Predicate;
 
 import static jetCheck.Generator.*;
 
@@ -17,7 +21,7 @@ public class ShrinkTest extends PropertyCheckerTestCase {
                      String s = l.toString();
                      return !"abcdefghijklmnopqrstuvwxyz()[]#!".chars().allMatch(c -> s.indexOf((char)c) >= 0);
                    },
-                   225);
+                   258);
   }
 
   public void testShrinkingNonEmptyList() {
@@ -27,4 +31,19 @@ public class ShrinkTest extends PropertyCheckerTestCase {
     assertEquals(1, list.size());
   }
 
+  public void testWhenEarlyObjectsCannotBeShrunkBeforeLater() {
+    Generator<String> gen = listsOf(IntDistribution.uniform(0, 2), listsOf(IntDistribution.uniform(0, 2), sampledFrom('a', 'b'))).map(List::toString);
+    Set<String> failing = new HashSet<>(Arrays.asList("[[a, b], [a, b]]", "[[a, b], [a]]", "[[a], [a]]", "[[a]]", "[]"));
+    Predicate<String> property = s -> !failing.contains(s);
+    checkFalsified(gen, property, 0); // prove that it sometimes fails
+    for (int i = 0; i < 1000; i++) {
+      try {
+        PropertyChecker.forAll(gen).shouldHold(property);
+      }
+      catch (PropertyFalsified e) {
+        assertEquals("[]", e.getBreakingValue());
+      }
+    }
+  }
+
 }