diff --git a/src/ostree/ot-admin-deploy.c b/src/ostree/ot-admin-deploy.c
index 21db4834..deda4eb2 100644
--- a/src/ostree/ot-admin-deploy.c
+++ b/src/ostree/ot-admin-deploy.c
@@ -791,10 +791,16 @@ parse_os_release (const char *contents,
   return ret;
 }
 
+/*
+ * install_deployment_kernel:
+ * 
+ * Write out an entry in /boot/loader/entries for @deployment.
+ */
 static gboolean
 install_deployment_kernel (GFile          *sysroot,
                            int             new_bootversion,
                            OtDeployment   *deployment,
+                           guint           n_deployments,
                            GCancellable   *cancellable,
                            GError        **error)
 
@@ -901,7 +907,7 @@ install_deployment_kernel (GFile          *sysroot,
                                val);
   ot_config_parser_set (bootconfig, "title", title_key);
 
-  version_key = g_strdup_printf ("%d", ot_deployment_get_bootserial (deployment));
+  version_key = g_strdup_printf ("%d", n_deployments - ot_deployment_get_index (deployment));
   ot_config_parser_set (bootconfig, "version", version_key);
 
   linux_relpath = g_file_get_relative_path (bootdir, dest_kernel_path);
@@ -1000,7 +1006,8 @@ ot_admin_write_deployments (GFile             *sysroot,
       for (i = 0; i < new_deployments->len; i++)
         {
           OtDeployment *deployment = new_deployments->pdata[i];
-          if (!install_deployment_kernel (sysroot, new_bootversion, deployment,
+          if (!install_deployment_kernel (sysroot, new_bootversion,
+                                          deployment, new_deployments->len,
                                           cancellable, error))
             {
               g_prefix_error (error, "Installing kernel: ");
diff --git a/src/ostree/ot-admin-functions.c b/src/ostree/ot-admin-functions.c
index 7dfc30f1..397aed25 100644
--- a/src/ostree/ot-admin-functions.c
+++ b/src/ostree/ot-admin-functions.c
@@ -717,8 +717,8 @@ list_deployments_process_one_boot_entry (GFile               *sysroot,
 }
 
 static gint
-compare_deployments_by_boot_loader_version (gconstpointer     a_pp,
-                                            gconstpointer     b_pp)
+compare_deployments_by_boot_loader_version_reversed (gconstpointer     a_pp,
+                                                     gconstpointer     b_pp)
 {
   OtDeployment *a = *((OtDeployment**)a_pp);
   OtDeployment *b = *((OtDeployment**)b_pp);
@@ -728,11 +728,15 @@ compare_deployments_by_boot_loader_version (gconstpointer     a_pp,
   const char *b_version = ot_config_parser_get (b_bootconfig, "version");
   
   if (a_version && b_version)
-    return strverscmp (a_version, b_version);
+    {
+      int r = strverscmp (a_version, b_version);
+      /* Reverse */
+      return -r;
+    }
   else if (a_version)
-    return 1;
-  else
     return -1;
+  else
+    return 1;
 }
 
 gboolean
@@ -766,7 +770,7 @@ ot_admin_list_deployments (GFile               *sysroot,
         goto out;
     }
 
-  g_ptr_array_sort (ret_deployments, compare_deployments_by_boot_loader_version);
+  g_ptr_array_sort (ret_deployments, compare_deployments_by_boot_loader_version_reversed);
   for (i = 0; i < ret_deployments->len; i++)
     {
       OtDeployment *deployment = ret_deployments->pdata[i];
diff --git a/tests/test-admin-deploy-1.sh b/tests/test-admin-deploy-1.sh
index 0119586b..fbf9fc27 100755
--- a/tests/test-admin-deploy-1.sh
+++ b/tests/test-admin-deploy-1.sh
@@ -62,6 +62,8 @@ assert_file_has_content sysroot/boot/loader/entries/ostree-testos-${rev}-0.conf
 assert_file_has_content sysroot/ostree/deploy/testos/deploy/${rev}.1/etc/os-release 'NAME=TestOS'
 assert_file_has_content sysroot/ostree/boot.0/testos/${bootcsum}/0/etc/os-release 'NAME=TestOS'
 
+ostree admin --sysroot=sysroot status
+
 echo "ok second deploy"
 
 ostree admin --sysroot=sysroot deploy --os=testos testos:testos/buildmaster/x86_64-runtime
@@ -123,6 +125,8 @@ assert_not_has_file sysroot/ostree/deploy/testos/deploy/${rev}.3/etc/aconfigfile
 
 echo "ok upgrade bare"
 
+ostree admin --sysroot=sysroot status
+
 os_repository_new_commit
 ostree --repo=sysroot/ostree/repo remote add testos file://$(pwd)/testos-repo testos/buildmaster/x86_64-runtime
 ostree admin --sysroot=sysroot upgrade --os=testos
@@ -134,14 +138,16 @@ assert_file_has_content sysroot/ostree/deploy/testos/deploy/${newrev}.0/etc/os-r
 
 echo "ok upgrade"
 
+ostree admin --sysroot=sysroot status
+
 assert_file_has_content sysroot/ostree/deploy/testos/deploy/${newrev}.0/etc/os-release 'NAME=TestOS'
 assert_file_has_content sysroot/ostree/deploy/testos/deploy/${origrev}.4/etc/os-release 'NAME=TestOS'
-ostree admin --sysroot=sysroot undeploy 1
+ostree admin --sysroot=sysroot undeploy 2
 assert_file_has_content sysroot/ostree/deploy/testos/deploy/${newrev}.0/etc/os-release 'NAME=TestOS'
 assert_not_has_dir sysroot/ostree/deploy/testos/deploy/${origrev}.4
 
 assert_file_has_content sysroot/ostree/deploy/testos/deploy/${origrev}.3/etc/os-release 'NAME=TestOS'
-ostree admin --sysroot=sysroot undeploy 3
+ostree admin --sysroot=sysroot undeploy 2
 assert_not_has_dir sysroot/ostree/deploy/testos/deploy/${origrev}.3
 
 assert_file_has_content sysroot/ostree/deploy/testos/deploy/${newrev}.0/etc/os-release 'NAME=TestOS'