diff --git a/letsencrypt-auto-source/letsencrypt-auto b/letsencrypt-auto-source/letsencrypt-auto
index 12be26e19..9973607be 100755
--- a/letsencrypt-auto-source/letsencrypt-auto
+++ b/letsencrypt-auto-source/letsencrypt-auto
@@ -912,6 +912,35 @@ OldVenvExists() {
     [ -n "$OLD_VENV_PATH" -a -f "$OLD_VENV_PATH/bin/letsencrypt" ]
 }
 
+# Given python path, version 1 and version 2, check if version 1 is outdated compared to version 2.
+# An unofficial version provided as version 1 (eg. 0.28.0.dev0) will be treated
+# specifically by printing "UNOFFICIAL". Otherwise, print "OUTDATED" if version 1
+# is outdated, and "UP_TO_DATE" if not.
+# This function relies only on installed python environment (2.x or 3.x) by certbot-auto.
+CompareVersions() {
+    "$1" - "$2" "$3" << "UNLIKELY_EOF"
+import sys
+from distutils.version import StrictVersion
+
+try:
+    current = StrictVersion(sys.argv[1])
+except ValueError:
+    sys.stdout.write('UNOFFICIAL')
+    sys.exit()
+
+try:
+    remote = StrictVersion(sys.argv[2])
+except ValueError:
+    sys.stdout.write('UP_TO_DATE')
+    sys.exit()
+
+if current < remote:
+    sys.stdout.write('OUTDATED')
+else:
+    sys.stdout.write('UP_TO_DATE')
+UNLIKELY_EOF
+}
+
 if [ "$1" = "--le-auto-phase2" ]; then
   # Phase 2: Create venv, install LE, and run.
 
@@ -1640,7 +1669,12 @@ UNLIKELY_EOF
       error "WARNING: couldn't find Python $MIN_PYTHON_VERSION+ to check for updates."
     elif ! REMOTE_VERSION=`"$LE_PYTHON" "$TEMP_DIR/fetch.py" --latest-version` ; then
       error "WARNING: unable to check for updates."
-    elif [ "$LE_AUTO_VERSION" != "$REMOTE_VERSION" ]; then
+    fi
+
+    LE_VERSION_STATE=`CompareVersions "$LE_PYTHON" "$LE_AUTO_VERSION" "$REMOTE_VERSION"`
+    if [ "$LE_VERSION_STATE" = "UNOFFICIAL" ]; then
+      say "Unofficial certbot-auto version detected, self-upgrade is disabled: $LE_AUTO_VERSION"
+    elif [ "$LE_VERSION_STATE" = "OUTDATED" ]; then
       say "Upgrading certbot-auto $LE_AUTO_VERSION to $REMOTE_VERSION..."
 
       # Now we drop into Python so we don't have to install even more
diff --git a/letsencrypt-auto-source/letsencrypt-auto.template b/letsencrypt-auto-source/letsencrypt-auto.template
index 6d2977832..f431e32e4 100755
--- a/letsencrypt-auto-source/letsencrypt-auto.template
+++ b/letsencrypt-auto-source/letsencrypt-auto.template
@@ -451,6 +451,35 @@ OldVenvExists() {
     [ -n "$OLD_VENV_PATH" -a -f "$OLD_VENV_PATH/bin/letsencrypt" ]
 }
 
+# Given python path, version 1 and version 2, check if version 1 is outdated compared to version 2.
+# An unofficial version provided as version 1 (eg. 0.28.0.dev0) will be treated
+# specifically by printing "UNOFFICIAL". Otherwise, print "OUTDATED" if version 1
+# is outdated, and "UP_TO_DATE" if not.
+# This function relies only on installed python environment (2.x or 3.x) by certbot-auto.
+CompareVersions() {
+    "$1" - "$2" "$3" << "UNLIKELY_EOF"
+import sys
+from distutils.version import StrictVersion
+
+try:
+    current = StrictVersion(sys.argv[1])
+except ValueError:
+    sys.stdout.write('UNOFFICIAL')
+    sys.exit()
+
+try:
+    remote = StrictVersion(sys.argv[2])
+except ValueError:
+    sys.stdout.write('UP_TO_DATE')
+    sys.exit()
+
+if current < remote:
+    sys.stdout.write('OUTDATED')
+else:
+    sys.stdout.write('UP_TO_DATE')
+UNLIKELY_EOF
+}
+
 if [ "$1" = "--le-auto-phase2" ]; then
   # Phase 2: Create venv, install LE, and run.
 
@@ -635,7 +664,12 @@ UNLIKELY_EOF
       error "WARNING: couldn't find Python $MIN_PYTHON_VERSION+ to check for updates."
     elif ! REMOTE_VERSION=`"$LE_PYTHON" "$TEMP_DIR/fetch.py" --latest-version` ; then
       error "WARNING: unable to check for updates."
-    elif [ "$LE_AUTO_VERSION" != "$REMOTE_VERSION" ]; then
+    fi
+
+    LE_VERSION_STATE=`CompareVersions "$LE_PYTHON" "$LE_AUTO_VERSION" "$REMOTE_VERSION"`
+    if [ "$LE_VERSION_STATE" = "UNOFFICIAL" ]; then
+      say "Unofficial certbot-auto version detected, self-upgrade is disabled: $LE_AUTO_VERSION"
+    elif [ "$LE_VERSION_STATE" = "OUTDATED" ]; then
       say "Upgrading certbot-auto $LE_AUTO_VERSION to $REMOTE_VERSION..."
 
       # Now we drop into Python so we don't have to install even more
diff --git a/letsencrypt-auto-source/tests/auto_test.py b/letsencrypt-auto-source/tests/auto_test.py
index c5109e208..16c478f20 100644
--- a/letsencrypt-auto-source/tests/auto_test.py
+++ b/letsencrypt-auto-source/tests/auto_test.py
@@ -27,6 +27,19 @@ def tests_dir():
     return dirname(abspath(__file__))
 
 
+def copy_stable(src, dst):
+    """
+    Copy letsencrypt-auto, and replace its current version to its equivalent stable one.
+    This is needed to test correctly the self-upgrade functionality.
+    """
+    copy(src, dst)
+    with open(dst, 'r') as file:
+        filedata = file.read()
+    filedata = re.sub(r'LE_AUTO_VERSION="(.*)\.dev0"', r'LE_AUTO_VERSION="\1"', filedata)
+    with open(dst, 'w') as file:
+        file.write(filedata)
+
+
 sys.path.insert(0, dirname(tests_dir()))
 from build import build as build_le_auto
 
@@ -343,7 +356,7 @@ class AutoTests(TestCase):
                          'v99.9.9/letsencrypt-auto': build_le_auto(version='99.9.9'),
                          'v99.9.9/letsencrypt-auto.sig': signed('something else')}
             with serving(resources) as base_url:
-                copy(LE_AUTO_PATH, le_auto_path)
+                copy_stable(LE_AUTO_PATH, le_auto_path)
                 try:
                     out, err = run_le_auto(le_auto_path, venv_dir, base_url)
                 except CalledProcessError as exc: