diff --git a/hibernate-core/src/main/java/org/hibernate/mapping/BasicValue.java b/hibernate-core/src/main/java/org/hibernate/mapping/BasicValue.java
index b506e49816..e9abeef45b 100644
--- a/hibernate-core/src/main/java/org/hibernate/mapping/BasicValue.java
+++ b/hibernate-core/src/main/java/org/hibernate/mapping/BasicValue.java
@@ -555,7 +555,7 @@ public class BasicValue extends SimpleValue implements JdbcTypeIndicators, Resol
 
 		@Override
 		public R toRelationalValue(Boolean domainValue) {
-			return underlyingJpaConverter.toRelationalValue( !domainValue );
+			return underlyingJpaConverter.toRelationalValue( domainValue != null ? !domainValue : null );
 		}
 
 		@Override
diff --git a/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanJavaType.java b/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanJavaType.java
index ec815ab0e9..fc0e62129c 100644
--- a/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanJavaType.java
+++ b/hibernate-core/src/main/java/org/hibernate/type/descriptor/java/BooleanJavaType.java
@@ -198,10 +198,7 @@ public class BooleanJavaType extends AbstractClassJavaType<Boolean> implements
 						(BasicValueConverter<Boolean, ?>) converter;
 				final Object falseValue = stringConverter.toRelationalValue( false );
 				final Object trueValue = stringConverter.toRelationalValue( true );
-				String[] values = new String[] {
-						falseValue != null ? falseValue.toString() : null,
-						trueValue != null ? trueValue.toString() : null
-				};
+				final String[] values = getPossibleStringValues( stringConverter, falseValue, trueValue );
 				return dialect.getCheckCondition( columnName, values );
 			}
 			else if ( jdbcType.isInteger() ) {
@@ -210,13 +207,48 @@ public class BooleanJavaType extends AbstractClassJavaType<Boolean> implements
 						(BasicValueConverter<Boolean, ? extends Number>) converter;
 				final Number falseValue = numericConverter.toRelationalValue( false );
 				final Number trueValue = numericConverter.toRelationalValue( true );
-				Long[] values = new Long[] {
-						falseValue != null ? Long.valueOf(falseValue.longValue()) : null,
-						trueValue != null ? Long.valueOf(trueValue.longValue()) : null
-				};
+				Long[] values = getPossibleNumericValues( numericConverter, falseValue, trueValue );
 				return dialect.getCheckCondition( columnName, values );
 			}
 		}
 		return null;
 	}
+
+	private static Long[] getPossibleNumericValues(
+			BasicValueConverter<Boolean, ? extends Number> numericConverter,
+			Number falseValue,
+			Number trueValue) {
+		Number nullValue = null;
+		try {
+			nullValue = numericConverter.toRelationalValue( null );
+		}
+		catch ( NullPointerException ignored ) {
+		}
+		Long[] values = new Long[nullValue != null ? 3 : 2];
+		values[0] = falseValue != null ? falseValue.longValue() : null;
+		values[1] = trueValue != null ? trueValue.longValue() : null;
+		if ( nullValue != null ) {
+			values[2] = nullValue.longValue();
+		}
+		return values;
+	}
+
+	private static String[] getPossibleStringValues(
+			BasicValueConverter<Boolean, ?> stringConverter,
+			Object falseValue,
+			Object trueValue) {
+		Object nullValue = null;
+		try {
+			nullValue =  stringConverter.toRelationalValue( null);
+		}
+		catch ( NullPointerException ignored ) {
+		}
+		final String[] values = new String[nullValue != null ? 3 : 2];
+		values[0] = falseValue != null ? falseValue.toString() : null;
+		values[1] = trueValue != null ? trueValue.toString() : null;
+		if ( nullValue != null ) {
+			values[2] =  nullValue.toString();
+		}
+		return values;
+	}
 }
diff --git a/hibernate-core/src/test/java/org/hibernate/orm/test/mapping/type/java/BooleanJavaTypeDescriptorTest.java b/hibernate-core/src/test/java/org/hibernate/orm/test/mapping/type/java/BooleanJavaTypeDescriptorTest.java
index df7831d4f5..227807a498 100644
--- a/hibernate-core/src/test/java/org/hibernate/orm/test/mapping/type/java/BooleanJavaTypeDescriptorTest.java
+++ b/hibernate-core/src/test/java/org/hibernate/orm/test/mapping/type/java/BooleanJavaTypeDescriptorTest.java
@@ -63,6 +63,15 @@ public class BooleanJavaTypeDescriptorTest {
         assertEquals("is_active in (0,1)", checkCondition);
     }
 
+    @Test
+    public void testCheckConditionShouldReturnCorrectStatementWhen1And0AndNullIntegerGiven() {
+        // given
+        // when
+        String checkCondition = underTest.getCheckCondition("is_active", IntegerJdbcType.INSTANCE, new TriStateBooleanConverter(), new AnyDialect());
+        // then
+        assertEquals("is_active in (0,1,-1)", checkCondition);
+    }
+
     @Test
     public void testWrapShouldReturnTrueWhenYStringGiven() {
         // given
@@ -176,4 +185,38 @@ public class BooleanJavaTypeDescriptorTest {
             return IntegerJavaType.INSTANCE;
         }
     }
+
+    private static class TriStateBooleanConverter implements AttributeConverter<Boolean, Integer>, BasicValueConverter<Boolean, Integer> {
+        @Override
+        public Integer convertToDatabaseColumn(Boolean attribute) {
+            if (attribute == null) return -1;
+            return  attribute ? 1 : 0;
+        }
+
+        @Override
+        public Boolean convertToEntityAttribute(Integer dbData) {
+            if (dbData == null || dbData == -1) return null;
+            return dbData == 1;
+        }
+
+        @Override
+        public @Nullable Boolean toDomainValue(@Nullable Integer relationalForm) {
+            return convertToEntityAttribute(relationalForm);
+        }
+
+        @Override
+        public @Nullable Integer toRelationalValue(@Nullable Boolean domainForm) {
+            return convertToDatabaseColumn(domainForm);
+        }
+
+        @Override
+        public JavaType<Boolean> getDomainJavaType() {
+            return BooleanJavaType.INSTANCE;
+        }
+
+        @Override
+        public JavaType<Integer> getRelationalJavaType() {
+            return IntegerJavaType.INSTANCE;
+        }
+    }
 }
\ No newline at end of file