diff --git a/rewrite-java/src/main/java/org/openrewrite/java/cleanup/SimplifyBooleanExpressionVisitor.java b/rewrite-java/src/main/java/org/openrewrite/java/cleanup/SimplifyBooleanExpressionVisitor.java
index 1c60f2692a0..22092471649 100644
--- a/rewrite-java/src/main/java/org/openrewrite/java/cleanup/SimplifyBooleanExpressionVisitor.java
+++ b/rewrite-java/src/main/java/org/openrewrite/java/cleanup/SimplifyBooleanExpressionVisitor.java
@@ -445,19 +445,24 @@ private boolean canSimplifyDoubleNegation(Expression innerExpression) {
     }
 
     /**
-     * Override this method to disable simplification of equals expressions,
-     * specifically for Kotlin while that is not yet part of the OpenRewrite/rewrite.
+     * Determines whether an equals comparison with a boolean literal can be simplified.
      * <p>
-     * Comparing Kotlin nullable type `?` with tree/false can not be simplified,
-     * e.g. `X?.fun() == true` is not equivalent to `X?.fun()`
+     * In Java, {@code x == true} can always be simplified to {@code x}.
+     * In Kotlin and other languages, nullable types like {@code Boolean?} compared
+     * with {@code == true} have different semantics than using the value directly,
+     * e.g. {@code nullableBoolean == true} evaluates to {@code false} when null,
+     * whereas using {@code nullableBoolean} directly would be a type error.
      * <p>
-     * Subclasses will want to check if the `org.openrewrite.kotlin.marker.IsNullSafe`
-     * marker is present.
+     * For non-Java languages, simplification is only allowed when the expression
+     * type is primitive boolean (non-nullable).
      *
      * @param j the expression to simplify
-     * @return true by default, unless overridden
+     * @return true if the equals comparison can be safely simplified
      */
     protected boolean shouldSimplifyEqualsOn(J j) {
-        return true;
+        if (getCursor().firstEnclosing(SourceFile.class) instanceof J.CompilationUnit) {
+            return true;
+        }
+        return j instanceof Expression && ((Expression) j).getType() == JavaType.Primitive.Boolean;
     }
 }
diff --git a/rewrite-kotlin/src/test/java/org/openrewrite/kotlin/cleanup/SimplifyBooleanExpressionVisitorTest.java b/rewrite-kotlin/src/test/java/org/openrewrite/kotlin/cleanup/SimplifyBooleanExpressionVisitorTest.java
new file mode 100644
index 00000000000..102f8600c20
--- /dev/null
+++ b/rewrite-kotlin/src/test/java/org/openrewrite/kotlin/cleanup/SimplifyBooleanExpressionVisitorTest.java
@@ -0,0 +1,111 @@
+/*
+ * Copyright 2026 the original author or authors.
+ * <p>
+ * 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
+ * <p>
+ * https://www.apache.org/licenses/LICENSE-2.0
+ * <p>
+ * 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 org.openrewrite.kotlin.cleanup;
+
+import org.junit.jupiter.api.Test;
+import org.openrewrite.Issue;
+import org.openrewrite.java.cleanup.SimplifyBooleanExpressionVisitor;
+import org.openrewrite.test.RecipeSpec;
+import org.openrewrite.test.RewriteTest;
+
+import static org.openrewrite.kotlin.Assertions.kotlin;
+import static org.openrewrite.test.RewriteTest.toRecipe;
+
+class SimplifyBooleanExpressionVisitorTest implements RewriteTest {
+
+    @Override
+    public void defaults(RecipeSpec spec) {
+        spec.recipe(toRecipe(() -> new SimplifyBooleanExpressionVisitor()));
+    }
+
+    @Issue("https://github.com/openrewrite/rewrite-static-analysis/issues/303")
+    @Test
+    void nullableReceiverEqualsTrue() {
+        rewriteRun(
+          kotlin(
+            """
+              fun Boolean?.toLegacyFlag() = if (this == true) "1" else "0"
+              """
+          )
+        );
+    }
+
+    @Issue("https://github.com/openrewrite/rewrite-static-analysis/issues/303")
+    @Test
+    void nullableVariableEqualsTrue() {
+        rewriteRun(
+          kotlin(
+            """
+              data class Todo(val completed: Boolean?)
+              fun main() {
+                  val todo = Todo(null)
+                  val isCompleted: Boolean = todo.completed == true
+              }
+              """
+          )
+        );
+    }
+
+    @Issue("https://github.com/openrewrite/rewrite-static-analysis/issues/303")
+    @Test
+    void nullableVariableEqualsFalse() {
+        rewriteRun(
+          kotlin(
+            """
+              fun check(b: Boolean?) {
+                  if (b == false) println("false or null")
+              }
+              """
+          )
+        );
+    }
+
+    @Issue("https://github.com/openrewrite/rewrite-static-analysis/issues/303")
+    @Test
+    void nullableVariableNotEqualTrue() {
+        rewriteRun(
+          kotlin(
+            """
+              fun check(b: Boolean?) {
+                  if (b != true) println("not true")
+              }
+              """
+          )
+        );
+    }
+
+    @Test
+    void simplifyBooleanLiteralOperations() {
+        rewriteRun(
+          kotlin(
+            """
+              fun check(b: Boolean) {
+                  val a = !false
+                  val c = b || true
+                  val d = b && false
+              }
+              """,
+            """
+              fun check(b: Boolean) {
+                  val a = true
+                  val c = true
+                  val d = false
+              }
+              """
+          )
+        );
+    }
+}