diff --git a/lib/jekyll/watcher.rb b/lib/jekyll/watcher.rb
index 3b1fe1b..8b7a3db 100644
--- a/lib/jekyll/watcher.rb
+++ b/lib/jekyll/watcher.rb
@@ -103,15 +103,16 @@ def listen_ignore_paths(options)
         next unless absolute_path.exist?
         begin
           relative_path = absolute_path.relative_path_from(source).to_s
+          relative_path = File.join(relative_path, "") if absolute_path.directory?
           unless relative_path.start_with?("../")
-            path_to_ignore = Regexp.new(Regexp.escape(relative_path))
+            path_to_ignore = %r!^#{Regexp.escape(relative_path)}!
             Jekyll.logger.debug "Watcher:", "Ignoring #{path_to_ignore}"
             path_to_ignore
           end
         rescue ArgumentError
           # Could not find a relative path
         end
-      end.compact + [%r!\.jekyll\-metadata!]
+      end.compact + [%r!^\.jekyll\-metadata!]
     end
 
     private
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index e681284..557e28b 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -73,4 +73,13 @@ def source_dir(*files)
   def dest_dir(*files)
     source_dir("_site", *files)
   end
+
+  def ignore_path?(patterns, path)
+    path = path.to_s
+    patterns.each do |pattern|
+      return true if path =~ pattern
+      next
+    end
+    false
+  end
 end
diff --git a/spec/watcher_spec.rb b/spec/watcher_spec.rb
index 31e290f..97b3ff9 100644
--- a/spec/watcher_spec.rb
+++ b/spec/watcher_spec.rb
@@ -12,7 +12,7 @@
 
   let(:options) { base_opts }
   let(:site)    { instance_double(Jekyll::Site) }
-  let(:default_ignored) { [%r!_config\.yml!, %r!_site!, %r!\.jekyll\-metadata!] }
+  let(:default_ignored) { [%r!^_config\.yml!, %r!^_site/!, %r!^\.jekyll\-metadata!] }
   subject { described_class }
   before(:each) do
     FileUtils.mkdir(options["destination"]) if options["destination"]
@@ -107,6 +107,10 @@
 
     it "ignores config.yml, .jekyll-metadata, and _site by default" do
       expect(ignored).to eql(default_ignored)
+      expect(ignore_path?(ignored, "_site/foo.html")).to eql(true)
+      expect(ignore_path?(ignored, "_sitemapper/foo.html")).to eql(false)
+      expect(ignore_path?(ignored, "bar/_site/foo.html")).to eql(false)
+      expect(ignore_path?(ignored, "bar/_site-mapper.html")).to eql(false)
     end
 
     context "with something excluded" do
@@ -119,19 +123,23 @@
       after(:each)  { FileUtils.rm(excluded_absolute) }
 
       it "ignores the excluded files" do
-        expect(ignored).to include(%r!README\.md!)
-        expect(ignored).to include(%r!LICENSE!)
+        expect(ignore_path?(ignored, "README.md")).to eql(true)
+        expect(ignore_path?(ignored, "LICENSE")).to eql(true)
       end
     end
 
     context "with a custom destination" do
-      let(:default_ignored) { [%r!_config\.yml!, %r!_dest!, %r!\.jekyll\-metadata!] }
+      let(:default_ignored) { [%r!^_config\.yml!, %r!^_dest/!, %r!^\.jekyll\-metadata!] }
 
       context "when source is absolute" do
         context "when destination is absolute" do
           let(:options) { base_opts.merge("destination" => source_dir("_dest")) }
           it "ignores the destination" do
             expect(ignored).to eql(default_ignored)
+            expect(ignore_path?(ignored, "_dest/foo.html")).to eql(true)
+            expect(ignore_path?(ignored, "_destination/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest-nation.html")).to eql(false)
           end
         end
 
@@ -139,6 +147,10 @@
           let(:options) { base_opts.merge("destination" => "spec/test-site/_dest") }
           it "ignores the destination" do
             expect(ignored).to eql(default_ignored)
+            expect(ignore_path?(ignored, "_dest/foo.html")).to eql(true)
+            expect(ignore_path?(ignored, "_destination/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest-nation.html")).to eql(false)
           end
         end
       end
@@ -155,6 +167,10 @@
           let(:options) { base_opts.merge("destination" => source_dir("_dest")) }
           it "ignores the destination" do
             expect(ignored).to eql(default_ignored)
+            expect(ignore_path?(ignored, "_dest/foo.html")).to eql(true)
+            expect(ignore_path?(ignored, "_destination/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest-nation.html")).to eql(false)
           end
         end
 
@@ -162,6 +178,10 @@
           let(:options) { base_opts.merge("destination" => "spec/test-site/_dest") }
           it "ignores the destination" do
             expect(ignored).to eql(default_ignored)
+            expect(ignore_path?(ignored, "_dest/foo.html")).to eql(true)
+            expect(ignore_path?(ignored, "_destination/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest/foo.html")).to eql(false)
+            expect(ignore_path?(ignored, "bar/_dest-nation.html")).to eql(false)
           end
         end
       end