diff --git a/lib/rubygems/version.rb b/lib/rubygems/version.rb
index 091858b7570e..b7966c3973f7 100644
--- a/lib/rubygems/version.rb
+++ b/lib/rubygems/version.rb
@@ -222,6 +222,7 @@ def initialize(version)
     end
     @version = -@version
     @segments = nil
+    @sort_key = compute_sort_key
   end
 
   ##
@@ -350,6 +351,12 @@ def <=>(other)
     end
 
     return unless Gem::Version === other
+
+    # Fast path for comparison when available.
+    if @sort_key && other.sort_key
+      return @sort_key <=> other.sort_key
+    end
+
     return 0 if @version == other.version || canonical_segments == other.canonical_segments
 
     lhsegments = canonical_segments
@@ -415,6 +422,21 @@ def freeze
 
   protected
 
+  attr_reader :sort_key # :nodoc:
+
+  def compute_sort_key
+    segments = canonical_segments
+    return if segments.size > 4 || prerelease? || segments.any? {|segment| segment > 65_000 }
+
+    base = 1_000_000_000_000
+
+    segments.sum do |segment|
+      result = segment * base
+      base /= 10_000
+      result
+    end
+  end
+
   def _segments
     # segments is lazy so it can pick up version values that come from
     # old marshaled versions, which don't go through marshal_load.
diff --git a/test/rubygems/test_gem_version.rb b/test/rubygems/test_gem_version.rb
index 3987c620d0a7..7ad085d48018 100644
--- a/test/rubygems/test_gem_version.rb
+++ b/test/rubygems/test_gem_version.rb
@@ -200,6 +200,37 @@ def test_semver
     assert_less_than "1.0.0-1", "1"
   end
 
+  def test_sort_key_is_computed_on_regular_release
+    refute_nil v("9.8.7").send(:sort_key)
+  end
+
+  def test_sort_key_is_computed_on_security_release
+    refute_nil v("9.8.7.1").send(:sort_key)
+  end
+
+  def test_sort_key_is_not_computed_on_prerelease
+    assert_nil v("9.8.7.pre1").send(:sort_key)
+  end
+
+  def test_sort_key_is_not_computed_on_version_with_more_segments
+    assert_nil v("1.1.1.1.1.1.1").send(:sort_key)
+  end
+
+  def test_sort_key_is_not_computed_on_huge_numbers
+    assert_nil v("2.30.1.250000").send(:sort_key)
+  end
+
+  def test_sort_key_is_used_for_comparison
+    a = v("18.0.1")
+    b = v("18.0.2")
+
+    # Ensure the slow path isn't getting hit
+    a.instance_variable_set(:@version, nil)
+    a.instance_variable_set(:@canonical_segments, nil)
+
+    assert_operator(a, :<, b)
+  end
+
   # modifying the segments of a version should not affect the segments of the cached version object
   def test_segments
     v("9.8.7").segments[2] += 1