diff --git a/sql/server/src/main/java/org/elasticsearch/xpack/sql/optimizer/Optimizer.java b/sql/server/src/main/java/org/elasticsearch/xpack/sql/optimizer/Optimizer.java
index 9c9a54509bb..45ab0b8606b 100644
--- a/sql/server/src/main/java/org/elasticsearch/xpack/sql/optimizer/Optimizer.java
+++ b/sql/server/src/main/java/org/elasticsearch/xpack/sql/optimizer/Optimizer.java
@@ -1149,10 +1149,10 @@ public class Optimizer extends RuleExecutor<LogicalPlan> {
                     return TRUE;
                 }
 
-                if (TRUE.equals(l)) {
+                if (FALSE.equals(l)) {
                     return r;
                 }
-                if (TRUE.equals(r)) {
+                if (FALSE.equals(r)) {
                     return l;
                 }
 
diff --git a/sql/server/src/test/java/org/elasticsearch/xpack/sql/optimizer/BooleanSimplificationTests.java b/sql/server/src/test/java/org/elasticsearch/xpack/sql/optimizer/BooleanSimplificationTests.java
new file mode 100644
index 00000000000..561d677c5e3
--- /dev/null
+++ b/sql/server/src/test/java/org/elasticsearch/xpack/sql/optimizer/BooleanSimplificationTests.java
@@ -0,0 +1,95 @@
+/*
+ * Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+ * or more contributor license agreements. Licensed under the Elastic License;
+ * you may not use this file except in compliance with the Elastic License.
+ */
+package org.elasticsearch.xpack.sql.optimizer;
+
+import org.elasticsearch.test.ESTestCase;
+import org.elasticsearch.xpack.sql.expression.Expression;
+import org.elasticsearch.xpack.sql.expression.Literal;
+import org.elasticsearch.xpack.sql.expression.predicate.And;
+import org.elasticsearch.xpack.sql.expression.predicate.Or;
+import org.elasticsearch.xpack.sql.optimizer.Optimizer.BooleanSimplification;
+import org.elasticsearch.xpack.sql.tree.Location;
+import org.elasticsearch.xpack.sql.type.DataType;
+import org.elasticsearch.xpack.sql.type.DataTypes;
+
+import java.util.Collections;
+
+public class BooleanSimplificationTests extends ESTestCase {
+
+    private static final Expression DUMMY_EXPRESSION = new DummyBooleanExpression(Location.EMPTY, 0);
+
+    private static class DummyBooleanExpression extends Expression {
+        
+        private final int id;
+        
+        public DummyBooleanExpression(Location location, int id) {
+            super(location, Collections.emptyList());
+            this.id = id;
+        }
+        
+        @Override
+        public boolean nullable() {
+            return false;
+        }
+
+        @Override
+        public DataType dataType() {
+            return DataTypes.BOOLEAN;
+        }
+
+        @Override
+        public int hashCode() {
+            int h = getClass().hashCode();
+            h = 31 * h + id;
+            return h;
+        }
+
+        @Override
+        public boolean equals(Object obj) {
+            if (obj == null || getClass() != obj.getClass()) {
+                return false;
+            }
+            return id == ((DummyBooleanExpression) obj).id;
+        }
+    }
+
+    public void testSimplifyOr() {
+        BooleanSimplification simplification = new BooleanSimplification();
+        
+        assertEquals(Literal.TRUE, simplification.rule(new Or(Location.EMPTY, Literal.TRUE, Literal.TRUE)));
+        assertEquals(Literal.TRUE, simplification.rule(new Or(Location.EMPTY, Literal.TRUE, DUMMY_EXPRESSION)));
+        assertEquals(Literal.TRUE, simplification.rule(new Or(Location.EMPTY, DUMMY_EXPRESSION, Literal.TRUE)));
+
+        assertEquals(Literal.FALSE, simplification.rule(new Or(Location.EMPTY, Literal.FALSE, Literal.FALSE)));
+        assertEquals(DUMMY_EXPRESSION, simplification.rule(new Or(Location.EMPTY, Literal.FALSE, DUMMY_EXPRESSION)));
+        assertEquals(DUMMY_EXPRESSION, simplification.rule(new Or(Location.EMPTY, DUMMY_EXPRESSION, Literal.FALSE)));
+    }
+
+    public void testSimplifyAnd() {
+        BooleanSimplification simplification = new BooleanSimplification();
+        
+        assertEquals(Literal.TRUE, simplification.rule(new And(Location.EMPTY, Literal.TRUE, Literal.TRUE)));
+        assertEquals(DUMMY_EXPRESSION, simplification.rule(new And(Location.EMPTY, Literal.TRUE, DUMMY_EXPRESSION)));
+        assertEquals(DUMMY_EXPRESSION, simplification.rule(new And(Location.EMPTY, DUMMY_EXPRESSION, Literal.TRUE)));
+
+        assertEquals(Literal.FALSE, simplification.rule(new And(Location.EMPTY, Literal.FALSE, Literal.FALSE)));
+        assertEquals(Literal.FALSE, simplification.rule(new And(Location.EMPTY, Literal.FALSE, DUMMY_EXPRESSION)));
+        assertEquals(Literal.FALSE, simplification.rule(new And(Location.EMPTY, DUMMY_EXPRESSION, Literal.FALSE)));
+    }
+
+    public void testCommonFactorExtraction() {
+        BooleanSimplification simplification = new BooleanSimplification();
+
+        Expression a = new DummyBooleanExpression(Location.EMPTY, 1);
+        Expression b = new DummyBooleanExpression(Location.EMPTY, 2);
+        Expression c = new DummyBooleanExpression(Location.EMPTY, 3);
+
+        Expression actual = new Or(Location.EMPTY, new And(Location.EMPTY, a, b), new And(Location.EMPTY, a, c));
+        Expression expected = new And(Location.EMPTY, a, new Or(Location.EMPTY, b, c));
+
+        assertEquals(expected, simplification.rule(actual));
+    }
+}