diff --git a/hyde/fs.py b/hyde/fs.py
index 31cbf98..d7ca3cd 100644
--- a/hyde/fs.py
+++ b/hyde/fs.py
@@ -236,7 +236,7 @@ class File(FS):
         determine age.
 
         """
-        return another_file.last_modified > self.last_modified
+        return File(str(another_file)).last_modified > self.last_modified
 
     @staticmethod
     def make_temp(text):
diff --git a/hyde/server.py b/hyde/server.py
index b0292cd..b850835 100644
--- a/hyde/server.py
+++ b/hyde/server.py
@@ -61,19 +61,22 @@ class HydeRequestHandler(SimpleHTTPRequestHandler):
         logger.info("Trying to load file based on request:[%s]" % result.path)
         path = result.path.lstrip('/')
         res = site.content.resource_from_relative_deploy_path(path)
+
         if not res:
+
             # Cannot find the source file using the given path.
             # Check if the target file exists in the deploy folder.
-            deployed = File(site.config.deploy_root_path.child(path))
-            if deployed.exists:
-              # this file is probably being generated by a plugin.
-              # lets not try too hard, just regenerate
-              self.server.regenerate()
-              return deployed.path
-            else:
-                logger.info("Cannot load file:[%s]" % path)
-                raise Exception("Cannot load file: [%s]" % path)
 
+            # this file is probably new or being generated by a plugin.
+            # lets not try too hard, just regenerate
+            logger.info("Attempting regeneration for:[%s]" % path)
+            self.server.regenerate()
+            res = site.content.resource_from_relative_deploy_path(path)
+            if not res:
+                # Nothing much we can do.
+                logger.error("Cannot load file:[%s]" % path)
+
+            return site.config.deploy_root_path.child(path)
         else:
             self.server.generate_resource(res)
         new_path = site.config.deploy_root_path.child(
@@ -105,6 +108,7 @@ class HydeWebServer(HTTPServer):
                                             HydeRequestHandler)
 
     def __reinit__(self):
+        self.site.load()
         self.generator = Generator(self.site)
         self.regenerate()
 
@@ -115,6 +119,7 @@ class HydeWebServer(HTTPServer):
         try:
             logger.info('Regenerating the entire site')
             self.generator.generate_all()
+            self.exception_count = 0
         except Exception, exception:
             self.exception_count += 1
             logger.error('Error occured when regenerating the site [%s]'
@@ -125,12 +130,16 @@ class HydeWebServer(HTTPServer):
 
     def generate_resource(self, resource):
         """
-        Regenerates the entire site.
+        Regenerates the given resource.
         """
-        try:
-            logger.info('Generating resource [%s]' % resource)
-            self.generator.generate_resource(resource)
-        except Exception, exception:
-            logger.error('Error [%s] occured when generating the resource [%s]'
+        target = self.site.config.deploy_root_path.child(
+                                resource.relative_deploy_path)
+        if File(target).older_than(resource.source_file):
+            try:
+                logger.info('Generating resource [%s]' % resource)
+                self.generator.generate_resource(resource)
+                self.exception_count = 0
+            except Exception, exception:
+                logger.error(
+                    'Error [%s] occured when generating the resource [%s]'
                             % (repr(exception), resource))
-            raise