diff --git a/src/libostree/ostree-sysroot.c b/src/libostree/ostree-sysroot.c
index 4dfd5edf26..1ff78b239a 100644
--- a/src/libostree/ostree-sysroot.c
+++ b/src/libostree/ostree-sysroot.c
@@ -1631,11 +1631,16 @@ ostree_sysroot_simple_write_deployment (OstreeSysroot      *sysroot,
   if (!booted_deployment && !merge_deployment && (retain_pending || retain_rollback))
     retain = TRUE;
 
+  /* tracks current versioned deployment */
+  OstreeRepo *repo = ostree_sysroot_repo (sysroot);
+  OstreeDeployment *versioned = booted_deployment ? booted_deployment : merge_deployment;
+  const gchar *last_version = NULL;
+  if (versioned)
+    last_version = _ostree_deployment_get_version (versioned, repo, error);
+
   /* tracks when we come across the booted deployment */
   gboolean before_booted = TRUE;
   gboolean before_merge = TRUE;
-  /* tracks last version */
-  const gchar *last_version = NULL;
   gboolean retained_previous_version = FALSE;
   for (guint i = 0; i < deployments->len; i++)
     {
@@ -1655,20 +1660,10 @@ ostree_sysroot_simple_write_deployment (OstreeSysroot      *sysroot,
       const gboolean passed_crossover = booted_deployment ? !before_booted : !before_merge;
 
       gboolean is_previous_version = FALSE;
-      if (!retained_previous_version)
+      if (passed_crossover && osname_matches && !retained_previous_version)
         {
-          OstreeRepo *repo = ostree_sysroot_repo (sysroot);
-          const gchar *deployment_version =
-            _ostree_deployment_get_version (deployment, repo, error);
-
-          if (deployment_version && *deployment_version)
-            {
-              if (!last_version)
-                last_version = deployment_version;
-
-              is_previous_version = (osname_matches && passed_crossover && last_version &&
-                                     (g_strcmp0 (deployment_version, last_version) != 0));
-            }
+          const gchar *version = _ostree_deployment_get_version (deployment, repo, error);
+          is_previous_version = version && (!last_version || (g_strcmp0 (version, last_version) < 0));
         }
 
       /* Retain deployment if:
@@ -1689,7 +1684,7 @@ ostree_sysroot_simple_write_deployment (OstreeSysroot      *sysroot,
       /*
        *   - we're keeping the previous version deployment
        */
-      else if (retain_previous && is_previous_version && !retained_previous_version)
+      else if (retain_previous && !retained_previous_version && is_previous_version)
         {
           g_ptr_array_add (new_deployments, g_object_ref (deployment));
           /* Just keep one previous version */