diff --git a/src/libostree/ostree-sysroot.c b/src/libostree/ostree-sysroot.c
index 71cf634668..b4af635562 100644
--- a/src/libostree/ostree-sysroot.c
+++ b/src/libostree/ostree-sysroot.c
@@ -1745,13 +1745,27 @@ ostree_sysroot_simple_write_deployment (OstreeSysroot      *sysroot,
 
   /* tracks current versioned deployment */
   OstreeRepo *repo = ostree_sysroot_repo (sysroot);
-  const gchar *last_version =
+  const gchar *new_version =
     _ostree_deployment_get_version (new_deployment, repo, error);
 
+  gboolean retained_previous_version = FALSE;
+  if (booted_deployment)
+    {
+      const gchar *booted_version =
+        _ostree_deployment_get_version (booted_deployment, repo, error);
+      retained_previous_version = (g_strcmp0 (booted_deployment, new_version) != 0);
+    }
+
+  if (!retained_previous_version && merge_deployment)
+    {
+      const gchar *merge_version =
+        _ostree_deployment_get_version (merge_deployment, repo, error);
+      retained_previous_version = (g_strcmp0 (merge_deployment, new_version) != 0);
+    }
+
   /* tracks when we come across the booted deployment */
   gboolean before_booted = TRUE;
   gboolean before_merge = TRUE;
-  gboolean retained_previous_version = FALSE;
   for (guint i = 0; i < deployments->len; i++)
     {
       OstreeDeployment *deployment = deployments->pdata[i];
@@ -1773,7 +1787,7 @@ ostree_sysroot_simple_write_deployment (OstreeSysroot      *sysroot,
       if (passed_crossover && osname_matches && !retained_previous_version)
         {
           const gchar *version = _ostree_deployment_get_version (deployment, repo, error);
-          is_previous_version = version && (!last_version || (g_strcmp0 (version, last_version) < 0));
+          is_previous_version = (g_strcmp0 (version, new_version) != 0);
         }
 
       /* Retain deployment if: