diff --git a/baseline-refaster-rules/src/main/java/com/palantir/baseline/refaster/AssertjOptionalIsNotPresent.java b/baseline-refaster-rules/src/main/java/com/palantir/baseline/refaster/AssertjOptionalIsNotPresent.java
new file mode 100644
index 000000000..4b1a28518
--- /dev/null
+++ b/baseline-refaster-rules/src/main/java/com/palantir/baseline/refaster/AssertjOptionalIsNotPresent.java
@@ -0,0 +1,49 @@
+/*
+ * (c) Copyright 2019 Palantir Technologies Inc. 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.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License 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 com.palantir.baseline.refaster;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import com.google.errorprone.refaster.ImportPolicy;
+import com.google.errorprone.refaster.annotation.AfterTemplate;
+import com.google.errorprone.refaster.annotation.BeforeTemplate;
+import com.google.errorprone.refaster.annotation.UseImportPolicy;
+import java.util.Optional;
+
+public final class AssertjOptionalIsNotPresent<T> {
+
+    @BeforeTemplate
+    void before1(Optional<T> thing) {
+        assertThat(thing.isPresent()).isFalse();
+    }
+
+    @BeforeTemplate
+    void before2(Optional<T> thing) {
+        assertThat(!thing.isPresent()).isTrue();
+    }
+
+    @BeforeTemplate
+    void before3(Optional<T> thing) {
+        assertThat(thing).isEqualTo(Optional.empty());
+    }
+
+    @AfterTemplate
+    @UseImportPolicy(ImportPolicy.STATIC_IMPORT_ALWAYS)
+    void after(Optional<T> thing) {
+        assertThat(thing).isNotPresent();
+    }
+}
diff --git a/baseline-refaster-rules/src/main/java/com/palantir/baseline/refaster/AssertjOptionalIsNotPresentWithDescription.java b/baseline-refaster-rules/src/main/java/com/palantir/baseline/refaster/AssertjOptionalIsNotPresentWithDescription.java
new file mode 100644
index 000000000..14c5ee3ef
--- /dev/null
+++ b/baseline-refaster-rules/src/main/java/com/palantir/baseline/refaster/AssertjOptionalIsNotPresentWithDescription.java
@@ -0,0 +1,49 @@
+/*
+ * (c) Copyright 2019 Palantir Technologies Inc. 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.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License 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 com.palantir.baseline.refaster;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import com.google.errorprone.refaster.ImportPolicy;
+import com.google.errorprone.refaster.annotation.AfterTemplate;
+import com.google.errorprone.refaster.annotation.BeforeTemplate;
+import com.google.errorprone.refaster.annotation.UseImportPolicy;
+import java.util.Optional;
+
+public final class AssertjOptionalIsNotPresentWithDescription<T> {
+
+    @BeforeTemplate
+    void before1(Optional<T> thing, String description) {
+        assertThat(thing.isPresent()).describedAs(description).isFalse();
+    }
+
+    @BeforeTemplate
+    void before2(Optional<T> thing, String description) {
+        assertThat(!thing.isPresent()).describedAs(description).isTrue();
+    }
+
+    @BeforeTemplate
+    void before3(Optional<T> thing, String description) {
+        assertThat(thing).describedAs(description).isEqualTo(Optional.empty());
+    }
+
+    @AfterTemplate
+    @UseImportPolicy(ImportPolicy.STATIC_IMPORT_ALWAYS)
+    void after(Optional<T> thing, String description) {
+        assertThat(thing).describedAs(description).isNotPresent();
+    }
+}
diff --git a/baseline-refaster-rules/src/test/java/com/palantir/baseline/refaster/AssertjOptionalPresenceTest.java b/baseline-refaster-rules/src/test/java/com/palantir/baseline/refaster/AssertjOptionalPresenceTest.java
index cf9648a47..cf7f81aa2 100644
--- a/baseline-refaster-rules/src/test/java/com/palantir/baseline/refaster/AssertjOptionalPresenceTest.java
+++ b/baseline-refaster-rules/src/test/java/com/palantir/baseline/refaster/AssertjOptionalPresenceTest.java
@@ -16,6 +16,8 @@
 
 package com.palantir.baseline.refaster;
 
+import static org.assertj.core.api.Assumptions.assumeThat;
+
 import org.junit.Test;
 
 public class AssertjOptionalPresenceTest {
@@ -65,4 +67,64 @@ public void isPresent_description() {
                         "  }",
                         "}");
     }
+
+    @Test
+    public void isNotPresent_simple() {
+        assumeThat(System.getProperty("java.specification.version"))
+                .describedAs("Refaster does not currently support fluent refactors on java 11")
+                .isEqualTo("1.8");
+        RefasterTestHelper
+                .forRefactoring(AssertjOptionalIsNotPresent.class)
+                .withInputLines(
+                        "Test",
+                        "import static org.assertj.core.api.Assertions.assertThat;",
+                        "import java.util.Optional;",
+                        "public class Test {",
+                        "  void f(Optional<String> in) {",
+                        "    assertThat(in.isPresent()).isFalse();",
+                        "    assertThat(!in.isPresent()).isTrue();",
+                        "    assertThat(in).isEqualTo(Optional.empty());",
+                        "  }",
+                        "}")
+                .hasOutputLines(
+                        "import static org.assertj.core.api.Assertions.assertThat;",
+                        "import java.util.Optional;",
+                        "public class Test {",
+                        "  void f(Optional<String> in) {",
+                        "    assertThat(in).isNotPresent();",
+                        "    assertThat(in).isNotPresent();",
+                        "    assertThat(in).isNotPresent();",
+                        "  }",
+                        "}");
+    }
+
+    @Test
+    public void isNotPresent_description() {
+        assumeThat(System.getProperty("java.specification.version"))
+                .describedAs("Refaster does not currently support fluent refactors on java 11")
+                .isEqualTo("1.8");
+        RefasterTestHelper
+                .forRefactoring(AssertjOptionalIsNotPresentWithDescription.class)
+                .withInputLines(
+                        "Test",
+                        "import static org.assertj.core.api.Assertions.assertThat;",
+                        "import java.util.Optional;",
+                        "public class Test {",
+                        "  void f(Optional<String> in) {",
+                        "    assertThat(in.isPresent()).describedAs(\"desc\").isFalse();",
+                        "    assertThat(!in.isPresent()).describedAs(\"desc\").isTrue();",
+                        "    assertThat(in).describedAs(\"desc\").isEqualTo(Optional.empty());",
+                        "  }",
+                        "}")
+                .hasOutputLines(
+                        "import static org.assertj.core.api.Assertions.assertThat;",
+                        "import java.util.Optional;",
+                        "public class Test {",
+                        "  void f(Optional<String> in) {",
+                        "    assertThat(in).describedAs(\"desc\").isNotPresent();",
+                        "    assertThat(in).describedAs(\"desc\").isNotPresent();",
+                        "    assertThat(in).describedAs(\"desc\").isNotPresent();",
+                        "  }",
+                        "}");
+    }
 }
diff --git a/changelog/@unreleased/pr-911.v2.yml b/changelog/@unreleased/pr-911.v2.yml
new file mode 100644
index 000000000..53da3b97c
--- /dev/null
+++ b/changelog/@unreleased/pr-911.v2.yml
@@ -0,0 +1,5 @@
+type: improvement
+improvement:
+  description: Add refaster rule to simplify empty optional asserts
+  links:
+  - https://github.com/palantir/gradle-baseline/pull/911