diff --git a/error-prone-contrib/pom.xml b/error-prone-contrib/pom.xml
index 172e1ce548..9f455e7838 100644
--- a/error-prone-contrib/pom.xml
+++ b/error-prone-contrib/pom.xml
@@ -143,6 +143,11 @@
             <artifactId>assertj-core</artifactId>
             <scope>provided</scope>
         </dependency>
+        <dependency>
+            <groupId>org.immutables</groupId>
+            <artifactId>value-annotations</artifactId>
+            <scope>test</scope>
+        </dependency>
         <dependency>
             <groupId>org.junit.jupiter</groupId>
             <artifactId>junit-jupiter-api</artifactId>
diff --git a/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/ImmutablesSortedSetComparator.java b/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/ImmutablesSortedSetComparator.java
new file mode 100644
index 0000000000..5e8a3c2c71
--- /dev/null
+++ b/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/ImmutablesSortedSetComparator.java
@@ -0,0 +1,81 @@
+package tech.picnic.errorprone.bugpatterns;
+
+import static com.google.errorprone.BugPattern.LinkType.NONE;
+import static com.google.errorprone.BugPattern.SeverityLevel.ERROR;
+import static com.google.errorprone.BugPattern.StandardTags.LIKELY_ERROR;
+import static com.google.errorprone.matchers.Matchers.allOf;
+import static com.google.errorprone.matchers.Matchers.anyOf;
+import static com.google.errorprone.matchers.Matchers.enclosingClass;
+import static com.google.errorprone.matchers.Matchers.hasAnnotation;
+import static com.google.errorprone.matchers.Matchers.hasModifier;
+import static com.google.errorprone.matchers.Matchers.isSubtypeOf;
+import static com.google.errorprone.matchers.Matchers.methodReturns;
+import static com.google.errorprone.matchers.Matchers.not;
+
+import com.google.auto.service.AutoService;
+import com.google.errorprone.BugPattern;
+import com.google.errorprone.VisitorState;
+import com.google.errorprone.bugpatterns.BugChecker;
+import com.google.errorprone.bugpatterns.BugChecker.MethodTreeMatcher;
+import com.google.errorprone.fixes.SuggestedFix;
+import com.google.errorprone.fixes.SuggestedFixes;
+import com.google.errorprone.matchers.Description;
+import com.google.errorprone.matchers.Matcher;
+import com.sun.source.tree.MethodTree;
+import java.util.SortedSet;
+import javax.lang.model.element.Modifier;
+
+/**
+ * A {@link BugChecker} which flags {@link SortedSet} property declarations inside
+ * {@code @Value.Immutable}- and {@code @Value.Modifiable}-annotated types that lack a
+ * {@code @Value.NaturalOrder} or {@code @Value.ReverseOrder} annotation.
+ *
+ * <p>Without such an annotation:
+ *
+ * <ul>
+ *   <li>deserialization of the enclosing type requires that the associated JSON property is
+ *       present, contrary to the way in which Immutables handles other collection properties; and
+ *   <li>different instances may use different comparator implementations (e.g. deserialization
+ *       would default to natural order sorting), potentially leading to subtle bugs.
+ * </ul>
+ */
+@AutoService(BugChecker.class)
+@BugPattern(
+    summary =
+        "`SortedSet` properties of a `@Value.Immutable` or `@Value.Modifiable` type must be "
+            + "annotated with `@Value.NaturalOrder` or `@Value.ReverseOrder`",
+    linkType = NONE,
+    severity = ERROR,
+    tags = LIKELY_ERROR)
+public final class ImmutablesSortedSetComparator extends BugChecker implements MethodTreeMatcher {
+  private static final long serialVersionUID = 1L;
+  private static final Matcher<MethodTree> METHOD_LACKS_ANNOTATION =
+      allOf(
+          methodReturns(isSubtypeOf(SortedSet.class)),
+          anyOf(
+              allOf(
+                  hasModifier(Modifier.ABSTRACT),
+                  enclosingClass(
+                      anyOf(
+                          hasAnnotation("org.immutables.value.Value.Immutable"),
+                          hasAnnotation("org.immutables.value.Value.Modifiable")))),
+              hasAnnotation("org.immutables.value.Value.Default")),
+          not(
+              anyOf(
+                  hasAnnotation("org.immutables.value.Value.NaturalOrder"),
+                  hasAnnotation("org.immutables.value.Value.ReverseOrder"))));
+
+  @Override
+  public Description matchMethod(MethodTree tree, VisitorState state) {
+    if (!METHOD_LACKS_ANNOTATION.matches(tree, state)) {
+      return Description.NO_MATCH;
+    }
+
+    SuggestedFix.Builder builder = SuggestedFix.builder();
+    String valueTypeIdentifier =
+        SuggestedFixes.qualifyType(state, builder, "org.immutables.value.Value");
+    return describeMatch(
+        tree,
+        builder.prefixWith(tree, String.format("@%s.NaturalOrder ", valueTypeIdentifier)).build());
+  }
+}
diff --git a/error-prone-contrib/src/test/java/tech/picnic/errorprone/bugpatterns/ImmutablesSortedSetComparatorTest.java b/error-prone-contrib/src/test/java/tech/picnic/errorprone/bugpatterns/ImmutablesSortedSetComparatorTest.java
new file mode 100644
index 0000000000..3942c6de1e
--- /dev/null
+++ b/error-prone-contrib/src/test/java/tech/picnic/errorprone/bugpatterns/ImmutablesSortedSetComparatorTest.java
@@ -0,0 +1,182 @@
+package tech.picnic.errorprone.bugpatterns;
+
+import com.google.errorprone.BugCheckerRefactoringTestHelper;
+import com.google.errorprone.BugCheckerRefactoringTestHelper.TestMode;
+import com.google.errorprone.CompilationTestHelper;
+import org.junit.jupiter.api.Test;
+
+final class ImmutablesSortedSetComparatorTest {
+  private final CompilationTestHelper compilationTestHelper =
+      CompilationTestHelper.newInstance(ImmutablesSortedSetComparator.class, getClass());
+  private final BugCheckerRefactoringTestHelper refactoringTestHelper =
+      BugCheckerRefactoringTestHelper.newInstance(ImmutablesSortedSetComparator.class, getClass());
+
+  @Test
+  void identification() {
+    compilationTestHelper
+        .addSourceLines(
+            "A.java",
+            "import com.google.common.collect.ContiguousSet;",
+            "import com.google.common.collect.ImmutableSet;",
+            "import com.google.common.collect.ImmutableSortedSet;",
+            "import java.util.NavigableSet;",
+            "import java.util.Set;",
+            "import java.util.SortedSet;",
+            "import java.util.TreeSet;",
+            "import org.immutables.value.Value;",
+            "",
+            "interface A {",
+            "  @Value.Immutable",
+            "  interface ImmutableInterface {",
+            "    Set<String> set();",
+            "",
+            "    // BUG: Diagnostic contains:",
+            "    SortedSet<String> sortedSet();",
+            "",
+            "    @Value.NaturalOrder",
+            "    SortedSet<String> sortedSet2();",
+            "  }",
+            "",
+            "  @Value.Modifiable",
+            "  interface ModifiableInterfaceWithDefaults {",
+            "    @Value.Default",
+            "    default Set<Integer> set() {",
+            "      return new TreeSet<>();",
+            "    }",
+            "",
+            "    @Value.Default",
+            "    // BUG: Diagnostic contains:",
+            "    default NavigableSet<Integer> navigableSet() {",
+            "      return new TreeSet<>();",
+            "    }",
+            "",
+            "    @Value.Default",
+            "    @Value.ReverseOrder",
+            "    default NavigableSet<Integer> navigableSet2() {",
+            "      return new TreeSet<>();",
+            "    }",
+            "",
+            "    default NavigableSet<Integer> nonPropertyNavigableSet() {",
+            "      return new TreeSet<>();",
+            "    }",
+            "  }",
+            "",
+            "  interface NonImmutablesInterface {",
+            "    SortedSet<String> sortedSet();",
+            "  }",
+            "",
+            "  @Value.Immutable",
+            "  abstract class AbstractImmutableWithDefaults {",
+            "    @Value.Default",
+            "    ImmutableSet<Integer> immutableSet() {",
+            "      return ImmutableSet.of();",
+            "    }",
+            "",
+            "    @Value.Default",
+            "    // BUG: Diagnostic contains:",
+            "    ImmutableSortedSet<String> immutableSortedSet() {",
+            "      return ImmutableSortedSet.of();",
+            "    }",
+            "",
+            "    @Value.Default",
+            "    @Value.NaturalOrder",
+            "    ImmutableSortedSet<String> immutableSortedSet2() {",
+            "      return ImmutableSortedSet.of();",
+            "    }",
+            "",
+            "    ImmutableSortedSet<String> nonPropertyImmutableSortedSet() {",
+            "      return ImmutableSortedSet.of();",
+            "    }",
+            "  }",
+            "",
+            "  @Value.Modifiable",
+            "  abstract class AbstractModifiable {",
+            "    abstract ImmutableSet<Integer> immutableSet();",
+            "",
+            "    // BUG: Diagnostic contains:",
+            "    abstract ContiguousSet<Integer> contiguousSet();",
+            "",
+            "    @Value.ReverseOrder",
+            "    abstract ContiguousSet<Integer> contiguousSet2();",
+            "  }",
+            "",
+            "  abstract class AbstractNonImmutables {",
+            "    abstract SortedSet<Integer> sortedSet();",
+            "  }",
+            "}")
+        .doTest();
+  }
+
+  @Test
+  void replacement() {
+    refactoringTestHelper
+        .addInputLines(
+            "A.java",
+            "import com.google.common.collect.ImmutableSortedSet;",
+            "import java.util.SortedSet;",
+            "import org.immutables.value.Value;",
+            "",
+            "@Value.Immutable",
+            "abstract class A {",
+            "  abstract ImmutableSortedSet<String> sortedSet();",
+            "",
+            "  @Value.Modifiable",
+            "  interface B {",
+            "    SortedSet<String> sortedSet();",
+            "  }",
+            "}")
+        .addOutputLines(
+            "A.java",
+            "import com.google.common.collect.ImmutableSortedSet;",
+            "import java.util.SortedSet;",
+            "import org.immutables.value.Value;",
+            "",
+            "@Value.Immutable",
+            "abstract class A {",
+            "  @Value.NaturalOrder",
+            "  abstract ImmutableSortedSet<String> sortedSet();",
+            "",
+            "  @Value.Modifiable",
+            "  interface B {",
+            "    @Value.NaturalOrder",
+            "    SortedSet<String> sortedSet();",
+            "  }",
+            "}")
+        .doTest(TestMode.TEXT_MATCH);
+  }
+
+  @Test
+  void replacementWithImportClash() {
+    refactoringTestHelper
+        .addInputLines(
+            "MySpringService.java",
+            "import com.google.common.collect.ImmutableSortedSet;",
+            "import org.springframework.beans.factory.annotation.Value;",
+            "",
+            "class MySpringService {",
+            "  MySpringService(@Value(\"${someProperty}\") String prop) {}",
+            "  ;",
+            "",
+            "  @org.immutables.value.Value.Immutable",
+            "  interface A {",
+            "    ImmutableSortedSet<String> sortedSet();",
+            "  }",
+            "}")
+        .addOutputLines(
+            "MySpringService.java",
+            "import com.google.common.collect.ImmutableSortedSet;",
+            "import org.springframework.beans.factory.annotation.Value;",
+            "",
+            "class MySpringService {",
+            "  MySpringService(@Value(\"${someProperty}\") String prop) {}",
+            "  ;",
+            "",
+            "  @org.immutables.value.Value.Immutable",
+            "  interface A {",
+            "    @org.immutables.value.Value.NaturalOrder",
+            "    ImmutableSortedSet<String> sortedSet();",
+            "  }",
+            "}")
+        .doTest(TestMode.TEXT_MATCH);
+  }
+}
diff --git a/pom.xml b/pom.xml
index f8d4dd71ec..b2a01c63b5 100644
--- a/pom.xml
+++ b/pom.xml
@@ -386,6 +386,11 @@
                 <artifactId>hamcrest-core</artifactId>
                 <version>2.2</version>
             </dependency>
+            <dependency>
+                <groupId>org.immutables</groupId>
+                <artifactId>value-annotations</artifactId>
+                <version>2.9.0</version>
+            </dependency>
             <dependency>
                 <groupId>org.junit</groupId>
                 <artifactId>junit-bom</artifactId>