diff --git a/src/lib/docpad.coffee b/src/lib/docpad.coffee
index dbd01af5..7af56f76 100755
--- a/src/lib/docpad.coffee
+++ b/src/lib/docpad.coffee
@@ -2684,7 +2684,7 @@ class DocPad extends EventEmitterEnhanced
 							return res.send(500)  unless database
 
 							# Serve the document to the user
-							document = database.findOne(relativePath: '404.html')
+							document = database.findOne(relativeOutPath: '404.html')
 							docpad.serveDocument({document,req,res,next,statusCode:404})
 
 						# 500 Middleware
@@ -2693,7 +2693,7 @@ class DocPad extends EventEmitterEnhanced
 							return res.send(500)  unless database
 
 							# Serve the document to the user
-							document = database.findOne(relativePath: '404.html')
+							document = database.findOne(relativeOutPath: '500.html')
 							docpad.serveDocument({document,req,res,next,statusCode:500,err})
 
 				# Start the Server
diff --git a/src/lib/models/document.coffee b/src/lib/models/document.coffee
index 882904a4..aa707e5f 100755
--- a/src/lib/models/document.coffee
+++ b/src/lib/models/document.coffee
@@ -336,12 +336,13 @@ class DocumentModel extends FileModel
 					changes.filenameRendered = filenameRendered
 
 				# Figure out the rendered url
-				if !url and filenameRendered
+				if filenameRendered
 					if relativeDirPath
-						url = "/#{relativeDirPath}/#{filenameRendered}"
+						relativeOutPath = "#{relativeDirPath}/#{filenameRendered}"
 					else
-						url = "/#{filenameRendered}"
-					changes.url = url
+						relativeOutPath = "#{filenameRendered}"
+					changes.relativeOutPath = relativeOutPath
+					changes.url = url = "/#{relativeOutPath}"  unless url
 
 				# Set name if it doesn't exist already
 				if !name and filenameRendered?
diff --git a/src/lib/models/file.coffee b/src/lib/models/file.coffee
index cccc10d9..193f4fac 100755
--- a/src/lib/models/file.coffee
+++ b/src/lib/models/file.coffee
@@ -60,12 +60,18 @@ class FileModel extends Model
 		# The full directory path of our source file
 		fullDirPath: null
 
-		# The final rendered path of our file
+		# The output path of our file
 		outPath: null
 
-		# The final rendered path of our file's directory
+		# The output path of our file's directory
 		outDirPath: null
 
+		# The relative output path of our file
+		relativeOutPath: null
+
+		# The relative output path of our file's directory
+		relativeOutDirPath: null
+
 		# The relative path of our source file (with extensions)
 		relativePath: null
 
@@ -447,6 +453,7 @@ class FileModel extends Model
 		# Fetch
 		{opts,next} = @getActionArgs(opts,next)
 		relativePath = @get('relativePath') or null
+		relativeDirPath = @get('relativeDirPath') or null
 		relativeBase = @get('relativeBase') or null
 		filename = @get('filename') or null
 		outPath = @get('outPath') or null
@@ -467,6 +474,8 @@ class FileModel extends Model
 
 		# Create the outPath if we have a outpute directory
 		if @outDirPath? and relativePath?
+			changes.relativeOutDirPath = relativeOutDirPath = relativeDirPath  if  relativeDirPath?
+			changes.relativeOutPath = relativeOutPath = relativePath
 			changes.outPath = outPath = pathUtil.join(@outDirPath,relativePath)
 			if outPath
 				changes.outDirPath = outDirPath = pathUtil.dirname(outPath)