diff --git a/middleman-core/lib/middleman-core/sources.rb b/middleman-core/lib/middleman-core/sources.rb
index d30f0124..f0d3cc91 100644
--- a/middleman-core/lib/middleman-core/sources.rb
+++ b/middleman-core/lib/middleman-core/sources.rb
@@ -116,7 +116,8 @@ module Middleman
     Contract Or[Symbol, HANDLER], Maybe[Hash] => HANDLER
     def watch(type_or_handler, options={})
       handler = if type_or_handler.is_a? Symbol
-        SourceWatcher.new(self, type_or_handler, options.delete(:path), options)
+        path = File.expand_path(options.delete(:path), app.root)
+        SourceWatcher.new(self, type_or_handler, path, options)
       else
         type_or_handler
       end
diff --git a/middleman-core/lib/middleman-core/sources/source_watcher.rb b/middleman-core/lib/middleman-core/sources/source_watcher.rb
index cbcf1fae..21d6d7b2 100644
--- a/middleman-core/lib/middleman-core/sources/source_watcher.rb
+++ b/middleman-core/lib/middleman-core/sources/source_watcher.rb
@@ -92,7 +92,7 @@ module Middleman
     # @return [void]
     Contract String => Any
     def update_path(directory)
-      @directory = Pathname(directory)
+      @directory = Pathname(File.expand_path(directory, app.root))
 
       stop_listener! if @listener
 
@@ -133,6 +133,7 @@ module Middleman
       return nil if p.absolute? && !p.to_s.start_with?(@directory.to_s)
 
       p = @directory + p if p.relative?
+
       if glob
         @extensionless_files[p]
       else