diff --git a/ebean-core/src/main/java/io/ebeaninternal/server/type/DefaultTypeManager.java b/ebean-core/src/main/java/io/ebeaninternal/server/type/DefaultTypeManager.java
index 401ad2216..81d6a1ea2 100644
--- a/ebean-core/src/main/java/io/ebeaninternal/server/type/DefaultTypeManager.java
+++ b/ebean-core/src/main/java/io/ebeaninternal/server/type/DefaultTypeManager.java
@@ -250,8 +250,7 @@ public final class DefaultTypeManager implements TypeManager {
   @Override
   public ScalarType<?> getScalarType(Class<?> type) {
     ScalarType<?> found = typeMap.get(type);
-    if (found == null || found == ScalarTypeNotFound.INSTANCE) {
-      found = null;
+    if (found == null) {
       if (type.getName().equals("org.joda.time.LocalTime")) {
         throw new IllegalStateException(
           "ScalarType of Joda LocalTime not defined. You need to set DatabaseConfig.jodaLocalTimeMode to"
@@ -259,19 +258,19 @@ public final class DefaultTypeManager implements TypeManager {
       }
       found = checkInheritedTypes(type);
     }
-    return found;
+    return found != ScalarTypeNotFound.INSTANCE ? found : null; // Do not return ScalarTypeNotFound, otherwise checks will fail
   }
 
   /**
    * Checks the typeMap for inherited types.
-   * 
-   * If <code>type</code> is a <code>GregorianCalendar</code>, then this method
+   *
+   * If e.g. <code>type</code> is a <code>GregorianCalendar</code>, then this method
    * will check the class hierarchy and will probably return a
    * <code>ScalarTypeCalendar</code> To speed up a second lookup, it will write
    * back the found scalarType to typeMap.
-   * 
-   * @param type
-   * @return
+   *
+   * @param type the for which to search for a <code>ScalarType</code>
+   * @return either a valid <code>ScalarType</code> if one could be found or {@link ScalarTypeNotFound#INSTANCE} if not
    */
   private ScalarType<?> checkInheritedTypes(Class<?> type) {
     // first step loop through inheritance chain
@@ -282,18 +281,18 @@ public final class DefaultTypeManager implements TypeManager {
         typeMap.put(type, found); // store type for next lookup
         return found;
       }
+      // second step - loop through interfaces of this type
+      for (Class<?> iface: parent.getInterfaces()) {
+        found = checkInheritedTypes(iface);
+        if (found != null && found != ScalarTypeNotFound.INSTANCE) {
+          typeMap.put(type, found); // store type for next lookup
+          return found;
+        }
+      }
       parent = parent.getSuperclass();
     }
-    // second step - loop through interface chain
-    for (Class<?> iface: type.getInterfaces()) {
-      ScalarType<?> found = checkInheritedTypes(iface);
-      if (found != null && found != ScalarTypeNotFound.INSTANCE) {
-        typeMap.put(type, found); // store type for next lookup
-        return found;
-      }
-    }
     typeMap.put(type, ScalarTypeNotFound.INSTANCE);
-    return null; // no success
+    return ScalarTypeNotFound.INSTANCE; // no success
   }
 
   @Override
@@ -399,7 +398,7 @@ public final class DefaultTypeManager implements TypeManager {
   private DocPropertyType getDocType(Type genericType) {
     if (genericType instanceof Class<?>) {
       ScalarType<?> found = getScalarType((Class<?>)genericType);
-      if (found != null && found != ScalarTypeNotFound.INSTANCE) {
+      if (found != null) {
         return found.getDocType();
       }
     }
diff --git a/ebean-test/src/test/java/org/tests/model/types/SomeNewTypesBean.java b/ebean-test/src/test/java/org/tests/model/types/SomeNewTypesBean.java
index 2596dbcba..1a0fee0bf 100644
--- a/ebean-test/src/test/java/org/tests/model/types/SomeNewTypesBean.java
+++ b/ebean-test/src/test/java/org/tests/model/types/SomeNewTypesBean.java
@@ -7,6 +7,7 @@ import javax.persistence.Version;
 import java.nio.file.Path;
 import java.sql.Date;
 import java.time.*;
+import java.util.Calendar;
 
 @Entity
 public class SomeNewTypesBean {
@@ -58,6 +59,8 @@ public class SomeNewTypesBean {
 
   Duration duration;
 
+  Calendar calendar;
+
   public Long getId() {
     return id;
   }
@@ -217,4 +220,12 @@ public class SomeNewTypesBean {
   public void setDuration(Duration duration) {
     this.duration = duration;
   }
+
+  public Calendar getCalendar() {
+    return calendar;
+  }
+
+  public void setCalendar(final Calendar calendar) {
+    this.calendar = calendar;
+  }
 }
diff --git a/ebean-test/src/test/java/org/tests/types/TestNewTypes.java b/ebean-test/src/test/java/org/tests/types/TestNewTypes.java
index 35732801e..a40c673ea 100644
--- a/ebean-test/src/test/java/org/tests/types/TestNewTypes.java
+++ b/ebean-test/src/test/java/org/tests/types/TestNewTypes.java
@@ -10,6 +10,8 @@ import org.tests.model.types.SomeNewTypesBean;
 import java.io.File;
 import java.nio.file.Paths;
 import java.time.*;
+import java.util.Calendar;
+import java.util.GregorianCalendar;
 import java.util.List;
 
 import static org.assertj.core.api.Assertions.assertThat;
@@ -44,6 +46,7 @@ public class TestNewTypes extends BaseTestCase {
     bean.setPath(Paths.get(TEMP_PATH));
     bean.setPeriod(Period.of(4,3,2));
     bean.setDuration(Duration.ofMinutes(5));
+    bean.setCalendar(Calendar.getInstance());
 
 
     DB.save(bean);
@@ -104,6 +107,9 @@ public class TestNewTypes extends BaseTestCase {
     list = DB.find(SomeNewTypesBean.class).where().eq("duration", Duration.ofMinutes(5)).findList();
     assertThat(list).isNotEmpty();
 
+    list = DB.find(SomeNewTypesBean.class).where().le("calendar", GregorianCalendar.getInstance()).findList();
+    assertThat(list).isNotEmpty();
+
     SomeNewTypesBean fetched = DB.find(SomeNewTypesBean.class, bean.getId());
 
     assertEquals(bean.getZoneId(), fetched.getZoneId());
@@ -122,6 +128,7 @@ public class TestNewTypes extends BaseTestCase {
     assertEquals(bean.getPath(), fetched.getPath());
     assertEquals(bean.getPeriod(), fetched.getPeriod());
     assertEquals(bean.getDuration(), fetched.getDuration());
+    assertEquals(bean.getCalendar(), fetched.getCalendar());
 
 
     String asJson = DB.json().toJson(fetched);
@@ -139,10 +146,10 @@ public class TestNewTypes extends BaseTestCase {
     assertThat(toBean.getOffsetDateTime()).isEqualToIgnoringNanos(bean.getOffsetDateTime());
     assertEquals(bean.getLocalTime().toSecondOfDay(), toBean.getLocalTime().toSecondOfDay());
     assertEquals(bean.getInstant().toEpochMilli() / 1000, toBean.getInstant().toEpochMilli() / 1000);
-    // FIXME: This test fails on Windows with: expected:<\tmp> but was:<C:\tmp>
     assertEquals(bean.getPath(), toBean.getPath());
     assertEquals(bean.getPeriod(), toBean.getPeriod());
     assertEquals(bean.getDuration(), toBean.getDuration());
+    assertEquals(bean.getCalendar(), toBean.getCalendar());
 
   }