diff --git a/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanTypeDescriptor.java b/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanTypeDescriptor.java
index 4c4cccbef6..991d4efe4c 100644
--- a/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanTypeDescriptor.java
+++ b/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanTypeDescriptor.java
@@ -95,11 +95,18 @@ public class BooleanTypeDescriptor extends AbstractTypeDescriptor<Boolean> {
 			return isTrue( (Character) value ) ? TRUE : FALSE;
 		}
 		if ( String.class.isInstance( value ) ) {
-			return isTrue( ( (String) value ).charAt( 0 ) ) ? TRUE : FALSE;
+			return isTrue((String) value) ? TRUE : FALSE;
 		}
 		throw unknownWrap( value.getClass() );
 	}
 
+	private boolean isTrue(String strValue) {
+		if (strValue != null && !strValue.isEmpty()) {
+			return isTrue(strValue.charAt(0));
+		}
+		return false;
+	}
+
 	private boolean isTrue(char charValue) {
 		return charValue == characterValueTrue || charValue == characterValueTrueLC;
 	}
diff --git a/hibernate-core/src/test/java/org/hibernate/type/descriptor/java/BooleanTypeDescriptorTest.java b/hibernate-core/src/test/java/org/hibernate/type/descriptor/java/BooleanTypeDescriptorTest.java
new file mode 100644
index 0000000000..f752d935cf
--- /dev/null
+++ b/hibernate-core/src/test/java/org/hibernate/type/descriptor/java/BooleanTypeDescriptorTest.java
@@ -0,0 +1,54 @@
+package org.hibernate.type.descriptor.java;
+
+import org.junit.Test;
+
+import static org.junit.Assert.*;
+
+public class BooleanTypeDescriptorTest {
+    private BooleanTypeDescriptor underTest = new BooleanTypeDescriptor();
+
+    @Test
+    public void testWrapShouldReturnTrueWhenYStringGiven() {
+        // given
+        // when
+        Boolean result = underTest.wrap("Y", null);
+        // then
+        assertTrue(result);
+    }
+
+    @Test
+    public void testWrapShouldReturnFalseWhenFStringGiven() {
+        // given
+        // when
+        Boolean result = underTest.wrap("N", null);
+        // then
+        assertFalse(result);
+    }
+
+    @Test
+    public void testWrapShouldReturnFalseWhenRandomStringGiven() {
+        // given
+        // when
+        Boolean result = underTest.wrap("k", null);
+        // then
+        assertFalse(result);
+    }
+
+    @Test
+    public void testWrapShouldReturnNullWhenNullStringGiven() {
+        // given
+        // when
+        Boolean result = underTest.wrap(null, null);
+        // then
+        assertNull(result);
+    }
+
+    @Test
+    public void testWrapShouldReturnFalseWhenEmptyStringGiven() {
+        // given
+        // when
+        Boolean result = underTest.wrap("", null);
+        // then
+        assertFalse(result);
+    }
+}
\ No newline at end of file