diff --git a/smithy-model/src/main/java/software/amazon/smithy/model/validation/validators/SensitiveTraitValidator.java b/smithy-model/src/main/java/software/amazon/smithy/model/validation/validators/SensitiveTraitValidator.java
new file mode 100644
index 00000000000..df0bda01dae
--- /dev/null
+++ b/smithy-model/src/main/java/software/amazon/smithy/model/validation/validators/SensitiveTraitValidator.java
@@ -0,0 +1,67 @@
+/*
+ * Copyright 2020 Amazon.com, Inc. or its affiliates. All Rights Reserved.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License").
+ * You may not use this file except in compliance with the License.
+ * A copy of the License is located at
+ *
+ *  http://aws.amazon.com/apache2.0
+ *
+ * or in the "license" file accompanying this file. This file is distributed
+ * on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either
+ * express or implied. See the License for the specific language governing
+ * permissions and limitations under the License.
+ */
+
+package software.amazon.smithy.model.validation.validators;
+
+import java.util.List;
+import java.util.Objects;
+import java.util.stream.Collectors;
+import software.amazon.smithy.model.Model;
+import software.amazon.smithy.model.shapes.MemberShape;
+import software.amazon.smithy.model.shapes.Shape;
+import software.amazon.smithy.model.shapes.SimpleShape;
+import software.amazon.smithy.model.traits.EnumTrait;
+import software.amazon.smithy.model.traits.SensitiveTrait;
+import software.amazon.smithy.model.validation.AbstractValidator;
+import software.amazon.smithy.model.validation.ValidationEvent;
+
+/**
+ * Finds members marked as sensitive that target shapes marked as sensitive,
+ * and find members marked as sensitive that target structures, unions, or
+ * enums.
+ */
+public final class SensitiveTraitValidator extends AbstractValidator {
+    @Override
+    public List<ValidationEvent> validate(Model model) {
+        return model.shapes(MemberShape.class)
+                .filter(member -> member.hasTrait(SensitiveTrait.class))
+                .map(member -> {
+                    Shape target = model.getShape(member.getTarget()).orElse(null);
+                    if (target == null) {
+                        return null;
+                    } else if (target.hasTrait(SensitiveTrait.class)) {
+                        return warning(member, member.expectTrait(SensitiveTrait.class),
+                                       "Redundant `sensitive` trait found on member that targets a `sensitive` shape");
+                    } else if (isBadSensitiveTarget(target)) {
+                        return warning(member, member.expectTrait(SensitiveTrait.class),
+                                "Members marked with the `sensitive` trait should not target shapes that represent "
+                                + "concrete data types like structures, unions, or enums. A better approach is to "
+                                + "instead mark the targeted shape as sensitive and omit the `sensitive` trait from "
+                                + "the member. This helps to prevent modeling mistakes by ensuring every reference "
+                                + "to concrete data types that are inherently sensitive are always considered "
+                                + "sensitive. Concrete types that are conditionally sensitive should generally be "
+                                + "separated into two types: one to represent a sensitive type and one to represent "
+                                + "the normal type.");
+                    }
+                    return null;
+                })
+                .filter(Objects::nonNull)
+                .collect(Collectors.toList());
+    }
+
+    private boolean isBadSensitiveTarget(Shape target) {
+        return !(target instanceof SimpleShape) || target.hasTrait(EnumTrait.class);
+    }
+}
diff --git a/smithy-model/src/main/resources/META-INF/services/software.amazon.smithy.model.validation.Validator b/smithy-model/src/main/resources/META-INF/services/software.amazon.smithy.model.validation.Validator
index c4106c59e47..f8d772407f4 100644
--- a/smithy-model/src/main/resources/META-INF/services/software.amazon.smithy.model.validation.Validator
+++ b/smithy-model/src/main/resources/META-INF/services/software.amazon.smithy.model.validation.Validator
@@ -25,6 +25,7 @@ software.amazon.smithy.model.validation.validators.ResourceCycleValidator
 software.amazon.smithy.model.validation.validators.ResourceIdentifierBindingValidator
 software.amazon.smithy.model.validation.validators.ResourceIdentifierValidator
 software.amazon.smithy.model.validation.validators.ResourceLifecycleValidator
+software.amazon.smithy.model.validation.validators.SensitiveTraitValidator
 software.amazon.smithy.model.validation.validators.ServiceValidator
 software.amazon.smithy.model.validation.validators.ShapeIdConflictValidator
 software.amazon.smithy.model.validation.validators.ShapeRecursionValidator
diff --git a/smithy-model/src/test/resources/software/amazon/smithy/model/errorfiles/validators/sensitive-trait-target.errors b/smithy-model/src/test/resources/software/amazon/smithy/model/errorfiles/validators/sensitive-trait-target.errors
new file mode 100644
index 00000000000..04a2fd2dafa
--- /dev/null
+++ b/smithy-model/src/test/resources/software/amazon/smithy/model/errorfiles/validators/sensitive-trait-target.errors
@@ -0,0 +1,2 @@
+[WARNING] smithy.example#Foo$baz: Members marked with the `sensitive` trait should not target shapes that represent concrete data types | SensitiveTrait
+[WARNING] smithy.example#Foo$qux: Redundant `sensitive` trait found on member that targets a `sensitive` shape | SensitiveTrait
diff --git a/smithy-model/src/test/resources/software/amazon/smithy/model/errorfiles/validators/sensitive-trait-target.smithy b/smithy-model/src/test/resources/software/amazon/smithy/model/errorfiles/validators/sensitive-trait-target.smithy
new file mode 100644
index 00000000000..44fd9bbe287
--- /dev/null
+++ b/smithy-model/src/test/resources/software/amazon/smithy/model/errorfiles/validators/sensitive-trait-target.smithy
@@ -0,0 +1,29 @@
+namespace smithy.example
+
+structure Foo {
+    // This is fine.
+    @sensitive
+    bar: String,
+
+    // This should warn.
+    @sensitive
+    baz: Baz,
+
+    // This is fine.
+    bam: SensitiveString,
+
+    // This is fine.
+    boo: Boo,
+
+    // This should warn for the redundant member trait.
+    @sensitive
+    qux: Boo
+}
+
+structure Baz {}
+
+@sensitive
+structure Boo {}
+
+@sensitive
+string SensitiveString