diff --git a/bin/aptible b/bin/aptible
index 3c0b22a0..f122d944 100755
--- a/bin/aptible
+++ b/bin/aptible
@@ -10,7 +10,7 @@ end
 begin
   Aptible::CLI::Agent.start
 rescue HyperResource::ClientError => e
-  m = if e.body['error'] == 'invalid_token'
+  m = if %w(invalid_token expired_token).include? e.body['error']
         'API authentication error: please run aptible login'
       else
         "An error occurred: #{e.body['message']}"
diff --git a/lib/aptible/cli/agent.rb b/lib/aptible/cli/agent.rb
index bdc3e24b..f604347e 100644
--- a/lib/aptible/cli/agent.rb
+++ b/lib/aptible/cli/agent.rb
@@ -235,11 +235,7 @@ def nag_toolbelt
 
       def warn_sso_enforcement
         # If the user is also a member of
-        begin
-          token = fetch_token
-        rescue StandardError
-          return
-        end
+        token = fetch_token
         reauth = Aptible::Auth::ReauthenticateOrganization.all(token: token)
         return if reauth.empty?
 
@@ -247,6 +243,7 @@ def warn_sso_enforcement
                          'login method (SSO or Aptible credentials) to access',
                          'these organizations:',
                          reauth.map(&:name)].join(' '))
+      rescue StandardError
       end
 
       def version_string
diff --git a/lib/aptible/cli/version.rb b/lib/aptible/cli/version.rb
index b143f764..33714c26 100644
--- a/lib/aptible/cli/version.rb
+++ b/lib/aptible/cli/version.rb
@@ -1,5 +1,5 @@
 module Aptible
   module CLI
-    VERSION = '0.16.8'.freeze
+    VERSION = '0.16.9'.freeze
   end
 end