diff --git a/lib/rubygems/version.rb b/lib/rubygems/version.rb
index 3ac3676d0a..25c412be4b 100644
--- a/lib/rubygems/version.rb
+++ b/lib/rubygems/version.rb
@@ -368,13 +368,13 @@ class Gem::Version
 
     lhsize = lhsegments.size
     rhsize = rhsegments.size
-    limit  = (lhsize > rhsize ? lhsize : rhsize) - 1
+    limit  = (lhsize > rhsize ? rhsize : lhsize)
 
     i = 0
 
-    while i <= limit
-      lhs = lhsegments[i] || 0
-      rhs = rhsegments[i] || 0
+    while i < limit
+      lhs = lhsegments[i]
+      rhs = rhsegments[i]
       i += 1
 
       next      if lhs == rhs
@@ -384,6 +384,24 @@ class Gem::Version
       return lhs <=> rhs
     end
 
+    lhs = lhsegments[i]
+
+    if lhs.nil?
+      rhs = rhsegments[i]
+
+      while i < rhsize
+        return 1 if String === rhs
+        return -1 unless rhs.zero?
+        rhs = rhsegments[i += 1]
+      end
+    else
+      while i < lhsize
+        return -1 if String === lhs
+        return 1 unless lhs.zero?
+        lhs = lhsegments[i += 1]
+      end
+    end
+
     0
   end