diff --git a/Gruntfile.js b/Gruntfile.js
index 31fc04444b..7aca0619c2 100644
--- a/Gruntfile.js
+++ b/Gruntfile.js
@@ -699,6 +699,8 @@ var path           = require('path'),
             var done = this.async();
             bootstrap().then(function () {
                 done();
+            }).catch(function (err) {
+                grunt.fail.fatal(err.stack);
             });
         });
 
diff --git a/core/bootstrap.js b/core/bootstrap.js
index 67664ca936..296818e0c6 100644
--- a/core/bootstrap.js
+++ b/core/bootstrap.js
@@ -13,7 +13,6 @@ var fs      = require('fs'),
 
     appRoot = config().paths.appRoot,
     configExample = config().paths.configExample,
-    rejectMessage = 'Unable to load config',
     configFile;
 
 function readConfigFile(envVal) {
@@ -27,25 +26,32 @@ function writeConfigFile() {
         if one doesn't exist. After that, start the server. */
     fs.exists(configExample, function checkTemplate(templateExists) {
         var read,
-            write;
+            write,
+            error;
 
         if (!templateExists) {
-            return errors.logError(new Error('Could not locate a configuration file.'), appRoot, 'Please check your deployment for config.js or config.example.js.');
+            error = new Error('Could not locate a configuration file.');
+            error.context = appRoot;
+            error.help = 'Please check your deployment for config.js or config.example.js.';
+
+            return written.reject(error);
         }
 
         // Copy config.example.js => config.js
         read = fs.createReadStream(configExample);
         read.on('error', function (err) {
-            /*jshint unused:false*/
-            return errors.logError(new Error('Could not open config.example.js for read.'), appRoot, 'Please check your deployment for config.js or config.example.js.');
+            errors.logError(new Error('Could not open config.example.js for read.'), appRoot, 'Please check your deployment for config.js or config.example.js.');
+
+            return written.reject(err);
         });
-        read.on('end', written.resolve);
 
         write = fs.createWriteStream(configFile);
         write.on('error', function (err) {
-            /*jshint unused:false*/
-            return errors.logError(new Error('Could not open config.js for write.'), appRoot, 'Please check your deployment for config.js or config.example.js.');
+            errors.logError(new Error('Could not open config.js for write.'), appRoot, 'Please check your deployment for config.js or config.example.js.');
+
+            return written.reject(err);
         });
+        write.on('finish', written.resolve);
 
         read.pipe(write);
     });
@@ -62,34 +68,39 @@ function validateConfigEnvironment() {
 
     try {
         config = readConfigFile(envVal);
-    } catch (ignore) {
-
+    }
+    catch (e) {
+        return when.reject(e);
     }
 
     // Check if we don't even have a config
     if (!config) {
-        errors.logError(new Error('Cannot find the configuration for the current NODE_ENV'), "NODE_ENV=" + envVal,
+        errors.logError(new Error('Cannot find the configuration for the current NODE_ENV'), 'NODE_ENV=' + envVal,
             'Ensure your config.js has a section for the current NODE_ENV value and is formatted properly.');
-        return when.reject(rejectMessage);
+
+        return when.reject(new Error('Unable to load config for NODE_ENV=' + envVal));
     }
 
     // Check that our url is valid
     if (!validator.isURL(config.url, { protocols: ['http', 'https'], require_protocol: true })) {
         errors.logError(new Error('Your site url in config.js is invalid.'), config.url, 'Please make sure this is a valid url before restarting');
-        return when.reject(rejectMessage);
+
+        return when.reject(new Error('invalid site url'));
     }
 
     parsedUrl = url.parse(config.url || 'invalid', false, true);
 
     if (/\/ghost(\/|$)/.test(parsedUrl.pathname)) {
         errors.logError(new Error('Your site url in config.js cannot contain a subdirectory called ghost.'), config.url, 'Please rename the subdirectory before restarting');
-        return when.reject(rejectMessage);
+
+        return when.reject(new Error('ghost subdirectory not allowed'));
     }
 
     // Check that we have database values
     if (!config.database || !config.database.client) {
         errors.logError(new Error('Your database configuration in config.js is invalid.'), JSON.stringify(config.database), 'Please make sure this is a valid Bookshelf database configuration');
-        return when.reject(rejectMessage);
+
+        return when.reject(new Error('invalid database configuration'));
     }
 
     hasHostAndPort = config.server && !!config.server.host && !!config.server.port;
@@ -98,7 +109,8 @@ function validateConfigEnvironment() {
     // Check for valid server host and port values
     if (!config.server || !(hasHostAndPort || hasSocket)) {
         errors.logError(new Error('Your server values (socket, or host and port) in config.js are invalid.'), JSON.stringify(config.server), 'Please provide them before restarting.');
-        return when.reject(rejectMessage);
+
+        return when.reject(new Error('invalid server configuration'));
     }
 
     return when.resolve(config);
@@ -118,9 +130,10 @@ function loadConfig(configFilePath) {
         if (!configExists) {
             pendingConfig = writeConfigFile();
         }
+
         when(pendingConfig).then(validateConfigEnvironment).then(function (rawConfig) {
             return config.init(rawConfig).then(loaded.resolve);
-        }).otherwise(loaded.reject);
+        }).catch(loaded.reject);
     });
 
     return loaded.promise;
diff --git a/core/index.js b/core/index.js
index ef168993f8..68651a3106 100644
--- a/core/index.js
+++ b/core/index.js
@@ -21,16 +21,16 @@ function startGhost(options) {
             var ghost = require('./server');
             return ghost(options.app)
                 .then(deferred.resolve)
-                    .otherwise(function (e) {
+                    .catch(function (err) {
                     // We don't return the rejected promise to stop
                     // the propagation of the rejection and just
                     // allow the user to manage what to do.
-                    deferred.reject(e);
+                    deferred.reject(err);
                 });
         } catch (e) {
             deferred.reject(e);
         }
-    });
+    }).catch(deferred.reject);
 
     return deferred.promise;
 }
diff --git a/core/test/unit/bootstrap_spec.js b/core/test/unit/bootstrap_spec.js
index 2c7fe92c88..fa241cdb94 100644
--- a/core/test/unit/bootstrap_spec.js
+++ b/core/test/unit/bootstrap_spec.js
@@ -15,7 +15,6 @@ var should         = require('should'),
 
 describe('Bootstrap', function () {
     var sandbox,
-        rejectMessage = bootstrap.__get__('rejectMessage'),
         overrideConfig = function (newConfig) {
             bootstrap.__set__('readConfigFile',  sandbox.stub().returns(
                 _.extend({}, defaultConfig, newConfig)
@@ -30,7 +29,6 @@ describe('Bootstrap', function () {
     afterEach(function () {
         bootstrap         = rewire('../../bootstrap');
         sandbox.restore();
-
     });
 
     it('loads the config file if one exists', function (done) {
@@ -120,7 +118,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -134,7 +132,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -148,7 +146,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -162,7 +160,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -176,7 +174,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -189,7 +187,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -202,7 +200,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -215,7 +213,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -229,7 +227,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -243,7 +241,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -258,7 +256,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -294,7 +292,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -307,7 +305,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);
@@ -320,7 +318,7 @@ describe('Bootstrap', function () {
             done(expectedError);
         }).catch(function (err) {
             should.exist(err);
-            err.should.contain(rejectMessage);
+            err.should.be.an.Error;
 
             done();
         }).catch(done);