diff --git a/src/main/java/com/avaje/ebeaninternal/server/query/SqlTreeNodeExtraJoin.java b/src/main/java/com/avaje/ebeaninternal/server/query/SqlTreeNodeExtraJoin.java
index 1b6ac4288..97d3a92a4 100644
--- a/src/main/java/com/avaje/ebeaninternal/server/query/SqlTreeNodeExtraJoin.java
+++ b/src/main/java/com/avaje/ebeaninternal/server/query/SqlTreeNodeExtraJoin.java
@@ -100,8 +100,9 @@ public class SqlTreeNodeExtraJoin implements SqlTreeNode {
 
     if (pathContainsMany) {
       // "promote" to left outer as the path contains a many
-      assocBeanProperty.addJoin(SqlJoinType.OUTER, prefix, ctx);
-    } else if (!manyToMany) {
+      joinType = SqlJoinType.OUTER;
+    }
+    if (!manyToMany) {
       assocBeanProperty.addJoin(joinType, prefix, ctx);
     }
 
diff --git a/src/test/java/com/avaje/tests/basic/TestM2MCascadeOne.java b/src/test/java/com/avaje/tests/basic/TestM2MCascadeOne.java
index 84d3014c6..dab31b421 100644
--- a/src/test/java/com/avaje/tests/basic/TestM2MCascadeOne.java
+++ b/src/test/java/com/avaje/tests/basic/TestM2MCascadeOne.java
@@ -2,6 +2,7 @@ package com.avaje.tests.basic;
 
 import java.util.List;
 
+import com.avaje.ebean.Query;
 import org.junit.Test;
 
 import com.avaje.ebean.BaseTestCase;
@@ -42,4 +43,16 @@ public class TestM2MCascadeOne extends BaseTestCase {
     Ebean.save(u1);
 
   }
+
+  @Test
+  public void testRawPredicate_with_ManyToManyPath() {
+
+    Query<MUser> query = Ebean.find(MUser.class)
+        .select("userid")
+        .where().raw("roles.roleid in (?)", 24)
+        .query();
+
+    query.findList();
+
+  }
 }