diff --git a/core/lib/Foswiki/Configure/Checkers/PubDir.pm b/core/lib/Foswiki/Configure/Checkers/PubDir.pm
index b731e91d12..5fdbbedecb 100755
--- a/core/lib/Foswiki/Configure/Checkers/PubDir.pm
+++ b/core/lib/Foswiki/Configure/Checkers/PubDir.pm
@@ -14,6 +14,15 @@ sub check {
     $this->{fileErrors} = 0;
     $this->{excessPerms} = 0;
     my $e = $this->guessMajorDir( 'PubDir', 'pub' );
+
+    $e .= $this->NOTE(<<MISSING
+If PubDir is missing, your ScriptDir is probably not located in the Foswiki
+installation directory.  All directory locations are guessed relative to the
+ScriptDir location. (<code>$Foswiki::cfg{ScriptDir}</code>)  Carefully review all of the Directory settings, especially
+the WorkingDir, which will be created in the guessed location after the settings are saved.
+MISSING
+) if ($e =~ m/Error/);
+
     $e .= $this->warnAboutWindowsBackSlashes( $Foswiki::cfg{PubDir} );
 
     # Don't check directories against {RCS} permissions on Windows
diff --git a/core/lib/Foswiki/Configure/Checkers/PubUrlPath.pm b/core/lib/Foswiki/Configure/Checkers/PubUrlPath.pm
index cb9396b49d..66c4cf3fc1 100755
--- a/core/lib/Foswiki/Configure/Checkers/PubUrlPath.pm
+++ b/core/lib/Foswiki/Configure/Checkers/PubUrlPath.pm
@@ -14,8 +14,8 @@ sub check {
         && $Foswiki::cfg{PubUrlPath} ne 'NOT SET' )
     {
         my $guess = $Foswiki::cfg{ScriptUrlPath};
-        $guess =~ s/bin$/pub/;
-        $guess = '/pub' unless ($guess);
+        $guess =~ s/\/.*?bin$/\/pub/;
+        $guess .= '/pub' unless ($guess =~ m/pub$/);
         $Foswiki::cfg{PubUrlPath} = $guess;
         return $this->guessed(0);
     }