diff --git a/src/client/models/conversation-list-store.vala b/src/client/models/conversation-list-store.vala
index 684b0ea4..f3b3cf19 100644
--- a/src/client/models/conversation-list-store.vala
+++ b/src/client/models/conversation-list-store.vala
@@ -245,7 +245,20 @@ public class ConversationListStore : Gtk.ListStore {
         folder_emails = new Gee.HashSet<Geary.EmailIdentifier>();
         account_emails = new Gee.HashSet<Geary.EmailIdentifier>();
         foreach (Geary.Conversation conversation in sorted_conversations) {
-            Geary.Email? need_preview = conversation.get_latest_email();
+            // find oldest unread message for the preview
+            Geary.Email? need_preview = null;
+            foreach (Geary.Email email in conversation.get_emails(Geary.Conversation.Ordering.DATE_ASCENDING)) {
+                if (email.email_flags.is_unread()) {
+                    need_preview = email;
+                    
+                    break;
+                }
+            }
+            
+            // if all are read, use newest message
+            if (need_preview == null)
+                need_preview = conversation.get_latest_email();
+            
             if (need_preview == null)
                 continue;
             
@@ -455,6 +468,11 @@ public class ConversationListStore : Gtk.ListStore {
     
     private void on_email_flags_changed(Geary.Conversation conversation) {
         refresh_flags(conversation);
+        
+        // refresh previews because the oldest unread message is displayed as the preview, and if
+        // that's changed, need to change the preview
+        // TODO: need support code to load preview for single conversation, not scan all
+        refresh_previews_async.begin(conversation_monitor);
     }
     
     private int sort_by_date(Gtk.TreeModel model, Gtk.TreeIter aiter, Gtk.TreeIter biter) {