diff --git a/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/MethodReferenceUsage.java b/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/MethodReferenceUsage.java
index 48659799e1..3a7c1de49c 100644
--- a/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/MethodReferenceUsage.java
+++ b/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/MethodReferenceUsage.java
@@ -100,6 +100,8 @@ private static Optional<SuggestedFix.Builder> constructMethodRef(
         .flatMap(statements -> constructMethodRef(lambdaExpr, statements.get(0)));
   }
 
+  // XXX: Replace nested `Optional` usage.
+  @SuppressWarnings("NestedOptionals")
   private static Optional<SuggestedFix.Builder> constructMethodRef(
       LambdaExpressionTree lambdaExpr, MethodInvocationTree subTree) {
     return matchArguments(lambdaExpr, subTree)
@@ -156,6 +158,8 @@ private static Optional<SuggestedFix.Builder> constructMethodRef(
     return constructFix(lambdaExpr, lhsType.tsym, subTree.getIdentifier());
   }
 
+  // XXX: Refactor or replace inner `Optional` with a custom type.
+  @SuppressWarnings("NestedOptionals")
   private static Optional<Optional<Name>> matchArguments(
       LambdaExpressionTree lambdaExpr, MethodInvocationTree subTree) {
     ImmutableList<Name> expectedArguments = getVariables(lambdaExpr);
diff --git a/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/NestedOptionals.java b/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/NestedOptionals.java
new file mode 100644
index 0000000000..a10ae529e4
--- /dev/null
+++ b/error-prone-contrib/src/main/java/tech/picnic/errorprone/bugpatterns/NestedOptionals.java
@@ -0,0 +1,51 @@
+package tech.picnic.errorprone.bugpatterns;
+
+import static com.google.errorprone.BugPattern.LinkType.NONE;
+import static com.google.errorprone.BugPattern.SeverityLevel.WARNING;
+import static com.google.errorprone.BugPattern.StandardTags.FRAGILE_CODE;
+
+import com.google.auto.service.AutoService;
+import com.google.common.collect.Iterables;
+import com.google.errorprone.BugPattern;
+import com.google.errorprone.VisitorState;
+import com.google.errorprone.bugpatterns.BugChecker;
+import com.google.errorprone.bugpatterns.BugChecker.MethodInvocationTreeMatcher;
+import com.google.errorprone.matchers.Description;
+import com.google.errorprone.suppliers.Supplier;
+import com.google.errorprone.suppliers.Suppliers;
+import com.google.errorprone.util.ASTHelpers;
+import com.sun.source.tree.MethodInvocationTree;
+import com.sun.source.tree.Tree;
+import com.sun.tools.javac.code.Type;
+import com.sun.tools.javac.util.List;
+import java.util.Optional;
+
+/** A {@link BugChecker} which flags nesting of {@link Optional Optionals}. */
+@AutoService(BugChecker.class)
+@BugPattern(
+    summary =
+        "Avoid nesting `Optional`s inside `Optional`s; the resultant code is hard to reason about",
+    linkType = NONE,
+    severity = WARNING,
+    tags = FRAGILE_CODE)
+public final class NestedOptionals extends BugChecker implements MethodInvocationTreeMatcher {
+  private static final long serialVersionUID = 1L;
+  private static final Supplier<Type> OPTIONAL = Suppliers.typeFromClass(Optional.class);
+
+  @Override
+  public Description matchMethodInvocation(MethodInvocationTree tree, VisitorState state) {
+    return isOptionalOfOptional(tree, state) ? describeMatch(tree) : Description.NO_MATCH;
+  }
+
+  private static boolean isOptionalOfOptional(Tree tree, VisitorState state) {
+    Type optionalType = OPTIONAL.get(state);
+    Type type = ASTHelpers.getType(tree);
+    if (!ASTHelpers.isSubtype(type, optionalType, state)) {
+      return false;
+    }
+
+    List<Type> typeArguments = type.getTypeArguments();
+    return !typeArguments.isEmpty()
+        && ASTHelpers.isSubtype(Iterables.getOnlyElement(typeArguments), optionalType, state);
+  }
+}
diff --git a/error-prone-contrib/src/main/java/tech/picnic/errorprone/refastertemplates/OptionalTemplates.java b/error-prone-contrib/src/main/java/tech/picnic/errorprone/refastertemplates/OptionalTemplates.java
index f84351a1e8..f35bd720a3 100644
--- a/error-prone-contrib/src/main/java/tech/picnic/errorprone/refastertemplates/OptionalTemplates.java
+++ b/error-prone-contrib/src/main/java/tech/picnic/errorprone/refastertemplates/OptionalTemplates.java
@@ -311,6 +311,7 @@ Optional<R> after(
   /** Prefer {@link Optional#or(Supplier)} over more verbose alternatives. */
   abstract static class OptionalOrOtherOptional<T> {
     @BeforeTemplate
+    @SuppressWarnings("NestedOptionals" /* Auto-fix for the `NestedOptionals` check. */)
     Optional<T> before(Optional<T> optional1, Optional<T> optional2) {
       // XXX: Note that rewriting the first and third variant will change the code's behavior if
       // `optional2` has side-effects.
diff --git a/error-prone-contrib/src/test/java/tech/picnic/errorprone/bugpatterns/NestedOptionalsTest.java b/error-prone-contrib/src/test/java/tech/picnic/errorprone/bugpatterns/NestedOptionalsTest.java
new file mode 100644
index 0000000000..d5154cf554
--- /dev/null
+++ b/error-prone-contrib/src/test/java/tech/picnic/errorprone/bugpatterns/NestedOptionalsTest.java
@@ -0,0 +1,42 @@
+package tech.picnic.errorprone.bugpatterns;
+
+import com.google.errorprone.CompilationTestHelper;
+import org.junit.jupiter.api.Test;
+
+final class NestedOptionalsTest {
+  private final CompilationTestHelper compilationTestHelper =
+      CompilationTestHelper.newInstance(NestedOptionals.class, getClass());
+
+  @Test
+  void identification() {
+    compilationTestHelper
+        .addSourceLines(
+            "A.java",
+            "import java.util.Optional;",
+            "import java.util.stream.Stream;",
+            "",
+            "class A {",
+            "  void m() {",
+            "    Optional.empty();",
+            "    Optional.of(1);",
+            "    // BUG: Diagnostic contains:",
+            "    Optional.of(Optional.empty());",
+            "    // BUG: Diagnostic contains:",
+            "    Optional.of(Optional.of(1));",
+            "",
+            "    Optional.ofNullable(null);",
+            "    // BUG: Diagnostic contains:",
+            "    Optional.ofNullable((Optional) null);",
+            "",
+            "    Optional.of(\"foo\").map(String::length);",
+            "    // BUG: Diagnostic contains:",
+            "    Optional.of(\"foo\").map(Optional::of);",
+            "",
+            "    Stream.of(\"foo\").findFirst();",
+            "    // BUG: Diagnostic contains:",
+            "    Stream.of(\"foo\").map(Optional::of).findFirst();",
+            "  }",
+            "}")
+        .doTest();
+  }
+}