Index: lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/persistence/Message.java
===================================================================
diff -u -r148812e61b3d92cfe06c5784af86e18d8765695d -r06fddd3d20bea904ede950bf0a3781fc5eb3fd64
--- lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/persistence/Message.java	(.../Message.java)	(revision 148812e61b3d92cfe06c5784af86e18d8765695d)
+++ lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/persistence/Message.java	(.../Message.java)	(revision 06fddd3d20bea904ede950bf0a3781fc5eb3fd64)
@@ -34,7 +34,7 @@
 import org.apache.commons.lang.builder.HashCodeBuilder;
 import org.apache.commons.lang.builder.ToStringBuilder;
 import org.apache.log4j.Logger;
-import org.lamsfoundation.lams.tool.forum.util.ForumToolContentHandler;
+import org.lamsfoundation.lams.tool.forum.util.AttachmentComparator;
 
 /**
  * @author conradb
@@ -70,7 +70,7 @@
     private Set sessionClones;
 
     public Message() {
-	attachments = new TreeSet();
+	attachments = new TreeSet<Attachment>(new AttachmentComparator());
 	sessionClones = new HashSet();
     }
 
@@ -110,7 +110,7 @@
 	    // clone attachment
 	    if (attachments != null) {
 		Iterator iter = attachments.iterator();
-		Set set = new TreeSet();
+		Set<Attachment> set = new TreeSet<Attachment>(new AttachmentComparator());
 		while (iter.hasNext()) {
 		    Attachment file = (Attachment) iter.next();
 		    Attachment newFile = (Attachment) file.clone();
Index: lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/util/AttachmentComparator.java
===================================================================
diff -u
--- lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/util/AttachmentComparator.java	(revision 0)
+++ lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/util/AttachmentComparator.java	(revision 06fddd3d20bea904ede950bf0a3781fc5eb3fd64)
@@ -0,0 +1,55 @@
+/**************************************************************** 
+ * Copyright (C) 2005 LAMS Foundation (http://lamsfoundation.org) 
+ * ============================================================= 
+ * License Information: http://lamsfoundation.org/licensing/lams/2.0/ 
+ * 
+ * This program is free software; you can redistribute it and/or modify 
+ * it under the terms of the GNU General Public License version 2.0 
+ * as published by the Free Software Foundation. 
+ * 
+ * This program is distributed in the hope that it will be useful, 
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of 
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the 
+ * GNU General Public License for more details. 
+ * 
+ * You should have received a copy of the GNU General Public License 
+ * along with this program; if not, write to the Free Software 
+ * Foundation, Inc., 51 Franklin Street, Fifth Floor, Boston, MA 02110-1301 * USA 
+ * 
+ * http://www.gnu.org/licenses/gpl.txt 
+ * **************************************************************** 
+ */  
+ 
+/* $Id$ */  
+package org.lamsfoundation.lams.tool.forum.util;
+
+import java.util.Comparator;
+
+import org.lamsfoundation.lams.tool.forum.persistence.Attachment;
+
+
+/**
+ * Attachment comparator by unique id, hence should be the order saved in the database.
+ */
+public class AttachmentComparator implements Comparator<Attachment> {
+
+    /**
+     * {@inheritDoc}
+     */
+    public int compare(Attachment o1, Attachment o2) {
+	if (o1 != null && o2 != null) {
+	    if ( o1.getUid() != null && o2.getUid() != null ) {
+		return (int) (o1.getUid() - o1.getUid());
+	    } else if ( o1.getUid() != null ) {
+		return (1);
+	    } else { 
+		return (-1);
+	    }
+	} else if (o1 != null) {
+	    return 1;
+	} else {
+	    return -1;
+	}
+    }
+
+}
\ No newline at end of file
Index: lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/web/actions/AuthoringAction.java
===================================================================
diff -u -r3323ab59f880fd09b8752ed7eeccf213d8f1e01f -r06fddd3d20bea904ede950bf0a3781fc5eb3fd64
--- lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/web/actions/AuthoringAction.java	(.../AuthoringAction.java)	(revision 3323ab59f880fd09b8752ed7eeccf213d8f1e01f)
+++ lams_tool_forum/src/java/org/lamsfoundation/lams/tool/forum/web/actions/AuthoringAction.java	(.../AuthoringAction.java)	(revision 06fddd3d20bea904ede950bf0a3781fc5eb3fd64)
@@ -68,6 +68,7 @@
 import org.lamsfoundation.lams.tool.forum.persistence.Message;
 import org.lamsfoundation.lams.tool.forum.persistence.PersistenceException;
 import org.lamsfoundation.lams.tool.forum.service.IForumService;
+import org.lamsfoundation.lams.tool.forum.util.AttachmentComparator;
 import org.lamsfoundation.lams.tool.forum.util.ForumConstants;
 import org.lamsfoundation.lams.tool.forum.util.ForumWebUtils;
 import org.lamsfoundation.lams.tool.forum.util.MessageComparator;
@@ -510,7 +511,7 @@
 	    for (ForumToolSession toolSession : toolSessions) {
 		Message newMsg = Message.newInstance(message);
 		newMsg.setToolSession(toolSession);
-		newMsg.setAttachments(new TreeSet());
+		newMsg.setAttachments(new TreeSet<Attachment>(new AttachmentComparator()));
 		newMsg.setModifiedBy(null);
 		newMsg.setCreatedBy(null);		
 		message.getSessionClones().add(newMsg);