diff --git a/Makefile b/Makefile
index f82c5670..3b38d1aa 100644
--- a/Makefile
+++ b/Makefile
@@ -8,7 +8,6 @@ PROBERTDIR=./probert
 PROBERT_REPO=https://github.com/canonical/probert
 DRYRUN?=--dry-run --bootloader uefi --machine-config examples/simple.json
 SYSTEM_SETUP_DRYRUN?=--dry-run
-RECONFIG?=--reconfigure
 export PYTHONPATH
 CWD := $(shell pwd)
 
@@ -57,10 +56,10 @@ dryrun-system-setup-server:
 	$(PYTHON) -m system_setup.cmd.server $(SYSTEM_SETUP_DRYRUN)
 
 dryrun-system-setup-recon:
-	$(PYTHON) -m system_setup.cmd.tui $(SYSTEM_SETUP_DRYRUN) $(RECONFIG)
+	DRYRUN_RECONFIG=true $(PYTHON) -m system_setup.cmd.tui $(SYSTEM_SETUP_DRYRUN)
 
 dryrun-system-setup-server-recon:
-	$(PYTHON) -m system_setup.cmd.server $(SYSTEM_SETUP_DRYRUN) $(RECONFIG)
+	DRYRUN_RECONFIG=true $(PYTHON) -m system_setup.cmd.server $(SYSTEM_SETUP_DRYRUN)
 
 lint: flake8
 
diff --git a/system_setup/client/client.py b/system_setup/client/client.py
index 2439f967..0d2d6f3a 100644
--- a/system_setup/client/client.py
+++ b/system_setup/client/client.py
@@ -15,6 +15,7 @@
 
 import logging
 import sys
+from system_setup.common.helpers import is_reconfigure
 
 from subiquity.client.client import SubiquityClient
 
@@ -40,15 +41,12 @@ class SystemSetupClient(SubiquityClient):
 
     def __init__(self, opts):
         # TODO WSL:
-        # 1. remove reconfigure flag
-        # 2. decide on which UI to show up based on existing user UID >=1000
-        #    (or default user set in wsl.conf?)
         # 3. provide an API for this for the flutter UI to know about it
-        # 4. Add Configuration Base page before Advanced
-        # 5. Add language page
-        # self.variant = "wsl_configuration"
-        if opts.reconfigure:
+
+        if is_reconfigure(opts.dry_run):
+            self.variant = "wsl_configuration"
             self.controllers = [
+                "Welcome",
                 "WSLConfigurationBase",
                 "WSLConfigurationAdvanced",
                 "Summary",
diff --git a/system_setup/cmd/tui.py b/system_setup/cmd/tui.py
index 92fb8c57..f70249b2 100755
--- a/system_setup/cmd/tui.py
+++ b/system_setup/cmd/tui.py
@@ -72,10 +72,6 @@ def make_client_args_parser():
                         help='Synthesize a click on a button matching PAT')
     parser.add_argument('--answers')
     parser.add_argument('--server-pid')
-    # TODO WSL: remove reconfigure flag and use dynamic decision (see below)
-    # Expose that as an endpoint on the server and decide in the client what
-    # to show
-    parser.add_argument('--reconfigure', action='store_true')
     return parser
 
 
diff --git a/system_setup/common/helpers.py b/system_setup/common/helpers.py
new file mode 100644
index 00000000..e1a788ed
--- /dev/null
+++ b/system_setup/common/helpers.py
@@ -0,0 +1,31 @@
+#!/usr/bin/env python3
+# Copyright 2015-2021 Canonical, Ltd.
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# 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 Affero General Public License for more details.
+#
+# You should have received a copy of the GNU Affero General Public License
+# along with this program.  If not, see <http://www.gnu.org/licenses/>.
+
+import os
+
+
+def is_reconfigure(is_dryrun):
+    is_dryrun_reconfigure = is_dryrun and \
+        os.getenv("DRYRUN_RECONFIG") == "true"
+    count = 0
+    with open('/etc/passwd', 'r') as f:
+        for line in f:
+            # check every normal user except nobody (65534)
+            if int(line.split(':')[2]) >= 1000 and \
+               int(line.split(':')[2]) != 65534:
+                count += 1
+    is_none_dryrun_normaluser = not is_dryrun and count != 0
+    return is_dryrun_reconfigure or is_none_dryrun_normaluser