diff --git a/core/server/middleware/index.js b/core/server/middleware/index.js
index 949514af92..9525747d5f 100644
--- a/core/server/middleware/index.js
+++ b/core/server/middleware/index.js
@@ -99,6 +99,7 @@ function activateTheme(activeTheme) {
     expressServer.enable(expressServer.get('activeTheme'));
     if (stackLocation) {
         expressServer.stack[stackLocation].handle = middleware.whenEnabled(expressServer.get('activeTheme'), middleware.staticTheme());
+        expressServer.stack[stackLocation].route = config.paths().webroot;
     }
 
     // set view engine
@@ -237,8 +238,8 @@ module.exports = function (server, dbHash) {
     expressServer.use(express.json());
     expressServer.use(express.urlencoded());
 
-    expressServer.use('/ghost/upload/', middleware.busboy);
-    expressServer.use('/ghost/api/v0.1/db/', middleware.busboy);
+    expressServer.use(root + '/ghost/upload/', middleware.busboy);
+    expressServer.use(root + '/ghost/api/v0.1/db/', middleware.busboy);
 
     // Session handling
     expressServer.use(express.cookieParser());
diff --git a/core/server/storage/localfilesystem.js b/core/server/storage/localfilesystem.js
index cc28744592..1103ad145a 100644
--- a/core/server/storage/localfilesystem.js
+++ b/core/server/storage/localfilesystem.js
@@ -33,7 +33,7 @@ localFileStore = _.extend(baseStore, {
         }).then(function () {
             // The src for the image must be in URI format, not a file system path, which in Windows uses \
             // For local file system storage can use relative path so add a slash
-            var fullUrl = ('/' + targetFilename).replace(new RegExp('\\' + path.sep, 'g'), '/');
+            var fullUrl = (config.paths().webroot + '/' + targetFilename).replace(new RegExp('\\' + path.sep, 'g'), '/');
             return saved.resolve(fullUrl);
         }).otherwise(function (e) {
             errors.logError(e);