diff --git a/bin/blt b/bin/blt
index 274414a83..1c87f57ea 100755
--- a/bin/blt
+++ b/bin/blt
@@ -18,6 +18,7 @@ $robo_namespaces = [
   'vm',
 ];
 $robo_commands = [
+  'doctor'
 ];
 
 $params_string = implode(' ', array_slice($argv, 1));
diff --git a/phing/tasks/blt.xml b/phing/tasks/blt.xml
index 102155ce2..da5686ac3 100644
--- a/phing/tasks/blt.xml
+++ b/phing/tasks/blt.xml
@@ -63,25 +63,6 @@
     <exec dir="${repo.root}" command="git commit -m 'Initial commit.'" logoutput="true" checkreturn="true" level="${blt.exec_level}" passthru="true"/>
   </target>
 
-  <target name="doctor" description="Inspects your local blt configuration for possible issues.">
-    <drush command="status" returnProperty="drush.return" haltonerror="false" passthru="false" verbose="false" logoutput="false">
-      <option name="include">../vendor/acquia/blt/drush</option>
-    </drush>
-    <if>
-      <equals arg1="${drush.return}" arg2="0"/>
-      <then>
-        <drush command="blt-doctor" verbose="false"  dir="${docroot}">
-          <option name="include">../vendor/acquia/blt/drush</option>
-        </drush>
-      </then>
-      <else>
-        <drush command="blt-doctor" verbose="false" dir="${docroot}" alias="" uri="">
-          <option name="include">../vendor/acquia/blt/drush</option>
-        </drush>
-      </else>
-    </if>
-  </target>
-
   <target name="blt:rsync-template" hidden="true">
     <echo>Copying files from BLT's template into your project...</echo>
     <exec dir="${repo.root}" command="rsync -a --no-g ${blt.root}/template/ ${repo.root}/ --exclude-from=${blt.update.ignore-existing-file}" logoutput="true" checkreturn="true" level="${blt.exec_level}" passthru="true"/>
diff --git a/scripts/drupal-vm/post-provision.sh b/scripts/drupal-vm/post-provision.sh
index 86d9c5690..47318aa70 100755
--- a/scripts/drupal-vm/post-provision.sh
+++ b/scripts/drupal-vm/post-provision.sh
@@ -7,6 +7,8 @@ then
     VAGRANT_MACHINE_NAME=$(grep vagrant_machine_name: "$CONFIG_FILE" | cut -d' ' -f 2)
     REPO_ROOT=/var/www/${VAGRANT_MACHINE_NAME}
     cd ${REPO_ROOT}
+else
+  echo "Could not find repo root!"
 fi
 
 # Add blt alias to front of .bashrc so that it applies to non-interactive shells.
diff --git a/src/Robo/Commands/Blt/DoctorCommand.php b/src/Robo/Commands/Blt/DoctorCommand.php
new file mode 100644
index 000000000..df639eaee
--- /dev/null
+++ b/src/Robo/Commands/Blt/DoctorCommand.php
@@ -0,0 +1,90 @@
+<?php
+
+namespace Acquia\Blt\Robo\Commands\Blt;
+
+use Acquia\Blt\Robo\BltTasks;
+use Symfony\Component\Yaml\Yaml;
+
+/**
+ * Defines commands in the "blt:doctor" namespace.
+ */
+class DoctorCommand extends BltTasks {
+
+  /**
+   * Inspects your local blt configuration for possible issues.
+   *
+   * @command doctor
+   */
+  public function doctor() {
+
+    if ($this->getInspector()->isDrupalVmLocallyInitialized() && $this->getInspector()->isDrupalVmBooted()) {
+      $result = $this->executeDoctorInsideVm();
+      if ($result->wasSuccessful()) {
+        return $result;
+      }
+    }
+
+    // Try BLT doctor with default alias. This might be a Drupal VM alias.
+    $alias = $this->getConfigValue('drush.alias');
+    $result = $this->executeDoctorOnHost($alias);
+
+    // If default alias failed, try again using @self alias.
+    if (!$result->wasSuccessful() && $alias != 'self') {
+      $this->logger->warning("Unable to run the doctor using @$alias. Trying with @self...");
+      $this->executeDoctorOnHost('self');
+    }
+
+    return $result;
+  }
+
+  /**
+   * Executes `blt doctor` inside Drupal VM.
+   *
+   * @return \Robo\Result
+   *   The command result.
+   */
+  protected function executeDoctorInsideVm() {
+    $drupal_vm_config = Yaml::parse(file_get_contents($this->getConfigValue('repo.root') . '/box/config.yml'));
+    $repo_root = $drupal_vm_config['vagrant_synced_folders'][0]['destination'];
+    $this->say("Drupal VM was detected. Running blt doctor inside of VM...");
+    $command = "cd $repo_root && $repo_root/vendor/bin/drush cc drush && $repo_root/vendor/bin/drush --include=$repo_root/vendor/acquia/blt/drush blt-doctor -r $repo_root/docroot";
+
+    return $this->executeCommandInDrupalVm($command);
+  }
+
+  /**
+   * Executes a command inside of Drupal VM.
+   *
+   * @param string $command
+   *   The command to execute.
+   *
+   * @return \Robo\Result
+   *   The command result.
+   */
+  protected function executeCommandInDrupalVm($command) {
+    $result = $this->taskExec("vagrant exec '$command'")
+      ->dir($this->getConfigValue('repo.root'))
+      ->detectInteractive()
+      ->run();
+
+    return $result;
+  }
+
+  /**
+   * Executes `blt doctor` on host machine.
+   *
+   * @return \Robo\Result
+   *   The command result.
+   */
+  protected function executeDoctorOnHost($alias) {
+    $drush_bin = $this->getConfigValue('composer.bin') . '/drush';
+    $include_dir = $this->getConfigValue('blt.root') . '/drush';
+    $result = $this->taskExec("$drush_bin @$alias --include=$include_dir blt-doctor")
+      ->dir($this->getConfigValue('docroot'))
+      ->detectInteractive()
+      ->run();
+
+    return $result;
+  }
+
+}
diff --git a/src/Robo/Commands/BltReleaseCommand.php b/src/Robo/Commands/BltReleaseCommand.php
index f413ff42a..a5dfe87a6 100644
--- a/src/Robo/Commands/BltReleaseCommand.php
+++ b/src/Robo/Commands/BltReleaseCommand.php
@@ -25,6 +25,8 @@ class BltReleaseCommand extends BltTasks {
    *
    * @option $update-changelog Update CHANGELOG.md. Defaults to true.
    *
+   * @hidden
+   *
    * @return int
    *   The CLI status code.
    */
diff --git a/src/Robo/Commands/Setup/BuildCommand.php b/src/Robo/Commands/Setup/BuildCommand.php
index 53290c902..db8f260b3 100644
--- a/src/Robo/Commands/Setup/BuildCommand.php
+++ b/src/Robo/Commands/Setup/BuildCommand.php
@@ -15,9 +15,11 @@ class BuildCommand extends BltTasks {
    * Install dependencies, builds docroot, installs Drupal.
    *
    * @command setup
+   *
+   * @aliases setup:all
    */
   public function setup() {
-    $this->say("Setting up local environment");
+    $this->say("Setting up local environment...");
     $status_code = $this->invokeCommands([
       'setup:build',
       'setup:hash-salt',
@@ -107,7 +109,7 @@ public function build() {
   }
 
   /**
-   * Installs composer dependencies.
+   * Installs Composer dependencies.
    *
    * @command setup:composer:install
    */
diff --git a/src/Robo/Commands/Setup/CloudHooksCommand.php b/src/Robo/Commands/Setup/CloudHooksCommand.php
index 3f8b4225b..2fb07c8d5 100644
--- a/src/Robo/Commands/Setup/CloudHooksCommand.php
+++ b/src/Robo/Commands/Setup/CloudHooksCommand.php
@@ -10,7 +10,7 @@
 class CloudHooksCommand extends BltTasks {
 
   /**
-   * Installs Acquia cloud hooks to hooks.
+   * Installs Acquia cloud hooks.
    *
    * @command setup:cloud-hooks
    */
diff --git a/src/Robo/Commands/Setup/ConfigCommand.php b/src/Robo/Commands/Setup/ConfigCommand.php
index 57ecc5264..6069baf0c 100644
--- a/src/Robo/Commands/Setup/ConfigCommand.php
+++ b/src/Robo/Commands/Setup/ConfigCommand.php
@@ -21,7 +21,7 @@ public function update() {
   }
 
   /**
-   * Import configuration from the config directory.
+   * Imports configuration from the config directory according to cm.strategy.
    *
    * @command setup:config-import
    */
@@ -52,49 +52,18 @@ public function import() {
 
       switch ($strategy) {
         case 'core-only':
-          if (file_exists($this->getConfigValue("cm.core.dirs.$cm_core_key.path") . '/core.extension.yml')) {
-            $task->exec("drush @$drush_alias config-import $cm_core_key --yes");
-          }
+          $this->importCoreOnly($task, $drush_alias, $cm_core_key);
           break;
 
         case 'config-split':
-          // We cannot use ${cm.core.dirs.${cm.core.key}.path} here because
-          // cm.core.key may be 'vcs', which does not have a path defined in
-          // BLT config. Perhaps this should be refactored.
-          $core_config_file = $this->getConfigValue('docroot') . '/' . $this->getConfigValue('cm.core.dirs.sync.path') . '/core.extension.yml';
-          if (file_exists($core_config_file)) {
-            $task->exec("drush @$drush_alias pm-enable config_split --yes");
-            $task->exec("drush @$drush_alias config-import sync --yes");
-          }
+          $this->importConfigSplit($task, $drush_alias);
           break;
 
         case 'features':
-          $task->exec("drush @$drush_alias config-import $cm_core_key --partial --yes");
-          if ($this->getConfig()->has('cm.features.bundle"')) {
-            $task->exec("drush @$drush_alias pm-enable features --yes");
-            // Clear drush caches to register features drush commands.
-            $task->exec("drush cc drush --yes");
-            foreach ($this->getConfigValue('cm.features.bundle') as $bundle) {
-              $task->exec("drush @$drush_alias features-revert-all --bundle=$bundle --yes");
-              // Revert all features again!
-              // @see https://www.drupal.org/node/2851532
-              $task->exec("drush @$drush_alias features-revert-all --bundle=$bundle --yes");
-            }
-          }
-          if ($this->getConfigValue('cm.features.no-overrides')) {
-            $this->say("Checking for features overrides...");
-            if ($this->getConfig()->has('cm.features.bundle')) {
-              foreach ($this->getConfigValue('cm.features.bundle') as $bundle) {
-                $features_overriden = $task->exec("drush fl --bundle=${bundle} | grep -Ei '(changed|conflicts|added)( *)$");
-                // @todo emit:
-                // A feature in the ${bundle} bundle is overridden. You must
-                // re-export this feature to incorporate the changes.
-                // @todo throw Exception.
-              }
-            }
-          }
+          $this->importFeatures($task, $drush_alias, $cm_core_key);
           break;
       }
+
       $task->exec("drush @$drush_alias cache-rebuild");
       $task->run();
 
@@ -103,4 +72,67 @@ public function import() {
     }
   }
 
+  /**
+   * Import configuration using core config management only.
+   *
+   * @param $task
+   * @param $drush_alias
+   * @param $cm_core_key
+   */
+  protected function importCoreOnly($task, $drush_alias, $cm_core_key) {
+    if (file_exists($this->getConfigValue("cm.core.dirs.$cm_core_key.path") . '/core.extension.yml')) {
+      $task->exec("drush @$drush_alias config-import $cm_core_key --yes");
+    }
+  }
+
+  /**
+   * Import configuration using config_split module.
+   *
+   * @param $task
+   * @param $drush_alias
+   */
+  protected function importConfigSplit($task, $drush_alias) {
+    // We cannot use ${cm.core.dirs.${cm.core.key}.path} here because
+    // cm.core.key may be 'vcs', which does not have a path defined in
+    // BLT config. Perhaps this should be refactored.
+    $core_config_file = $this->getConfigValue('docroot') . '/' . $this->getConfigValue('cm.core.dirs.sync.path') . '/core.extension.yml';
+    if (file_exists($core_config_file)) {
+      $task->exec("drush @$drush_alias pm-enable config_split --yes");
+      $task->exec("drush @$drush_alias config-import sync --yes");
+    }
+  }
+
+  /**
+   * Import configuration using features module.
+   * @param $task
+   * @param $drush_alias
+   * @param $cm_core_key
+   */
+  protected function importFeatures($task, $drush_alias, $cm_core_key) {
+    $task->exec("drush @$drush_alias config-import $cm_core_key --partial --yes");
+    if ($this->getConfig()->has('cm.features.bundle"')) {
+      $task->exec("drush @$drush_alias pm-enable features --yes");
+      // Clear drush caches to register features drush commands.
+      $task->exec("drush cc drush --yes");
+      foreach ($this->getConfigValue('cm.features.bundle') as $bundle) {
+        $task->exec("drush @$drush_alias features-revert-all --bundle=$bundle --yes");
+        // Revert all features again!
+        // @see https://www.drupal.org/node/2851532
+        $task->exec("drush @$drush_alias features-revert-all --bundle=$bundle --yes");
+      }
+    }
+    if ($this->getConfigValue('cm.features.no-overrides')) {
+      $this->say("Checking for features overrides...");
+      if ($this->getConfig()->has('cm.features.bundle')) {
+        foreach ($this->getConfigValue('cm.features.bundle') as $bundle) {
+          $features_overriden = $task->exec("drush fl --bundle=${bundle} | grep -Ei '(changed|conflicts|added)( *)$");
+          // @todo emit:
+          // A feature in the ${bundle} bundle is overridden. You must
+          // re-export this feature to incorporate the changes.
+          // @todo throw Exception.
+        }
+      }
+    }
+  }
+
 }
diff --git a/src/Robo/Commands/Setup/SettingsCommand.php b/src/Robo/Commands/Setup/SettingsCommand.php
index 8d2c25b23..2bd2f56e3 100644
--- a/src/Robo/Commands/Setup/SettingsCommand.php
+++ b/src/Robo/Commands/Setup/SettingsCommand.php
@@ -55,8 +55,9 @@ public function generateSiteConfigFiles() {
 
       $this->taskFilesystemStack()
         ->chmod($multisite_dir, 0777)
+        // @todo Might need to check that this file exists before chmoding it.
+        ->chmod($project_settings_file, 0777)
         ->copy($project_default_settings_file, $project_settings_file)
-        ->copy($project_settings_file, 0777)
         ->copy($blt_local_settings_file, $default_local_settings_file)
         ->copy($default_local_settings_file, $project_local_settings_file)
         ->copy($blt_local_drush_file, $default_local_drush_file)
@@ -87,7 +88,7 @@ public function generateSiteConfigFiles() {
    * @command setup:behat
    */
   public function behat() {
-    $this->say("Generating Behat configuration files");
+    $this->say("Generating Behat configuration files...");
     $this->taskFilesystemStack()
       ->copy($this->defaultBehatLocalConfigFile, $this->projectBehatLocalConfigFile)
       ->stopOnFail()
@@ -97,7 +98,7 @@ public function behat() {
   }
 
   /**
-   * Installs git hooks to local .git/hooks directory.
+   * Installs BLT git hooks to local .git/hooks directory.
    *
    * @command setup:git-hooks
    */
@@ -117,7 +118,7 @@ public function gitHooks() {
    */
   protected function installGitHook($hook) {
     if ($this->getConfigValue('git.hooks.' . $hook)) {
-      $this->say("Installing $hook git hook");
+      $this->say("Installing $hook git hook...");
       $source = $this->getConfigValue('git.hooks.' . $hook) . "/$hook";
       $dest = $this->getConfigValue('repo.root') . "/.git/hooks/$hook";
 
diff --git a/src/Robo/Commands/Vm/VmCommand.php b/src/Robo/Commands/Vm/VmCommand.php
index 7fc86d7f4..e2691bbea 100644
--- a/src/Robo/Commands/Vm/VmCommand.php
+++ b/src/Robo/Commands/Vm/VmCommand.php
@@ -45,6 +45,8 @@ public function initialize() {
    *
    * @command vm
    *
+   * @aliases vm:all
+   *
    * @options no-boot
    */
   public function vm($options = ['no-boot' => FALSE]) {
@@ -137,13 +139,13 @@ public function config() {
 
     $this->getConfig()->expandFileProperties($this->projectDrupalVmConfigFile);
 
-    $this->say("<info>BLT has created default configuration for your Drupal VM</info>");
-    $this->say("The configuration file is {$this->projectDrupalVmConfigFile}.");
+    $this->say("<info>BLT has created default configuration for your Drupal VM.</info>");
+    $this->say("The configuration file is <comment>{$this->projectDrupalVmConfigFile}</comment>.");
 
-    $this->say("To customize the VM, follow the Quick Start Guide in Drupal VM's README.");
-    $this->say("https://github.com/geerlingguy/drupal-vm#quick-start-guide");
+    $this->say("To customize the VM, follow the Quick Start Guide in Drupal VM's README:");
+    $this->say("<comment>https://github.com/geerlingguy/drupal-vm#quick-start-guide</comment>");
 
-    $this->say("To run drush commands against the VM, use the {$this->drupalVmAlias} alias.");
+    $this->say("To run drush commands against the VM, use the <comment>@{$this->drupalVmAlias}</comment> alias.");
     $this->yell("From now on, please use vagrant commands to manage your virtual machine.");
   }
 
@@ -166,8 +168,8 @@ protected function localInitialize() {
     $yaml = Yaml::dump($contents, 3, 2);
     file_put_contents($filename, $yaml);
 
-    $this->say("$filename was modified");
-    $this->say("BLT will now use @{$contents['drush']['default_alias']} as the default drush alias for all commands.");
+    $this->say("$filename was modified.");
+    $this->say("BLT will now use <comment>@{$contents['drush']['default_alias']}</comment> as the default drush alias for all commands.");
   }
 
   /**
@@ -176,11 +178,24 @@ protected function localInitialize() {
   protected function boot() {
     $confirm = $this->confirm("Do you want to boot Drupal VM?", TRUE);
     if ($confirm) {
-      $this->say("In future, run `vagrant up` to boot the VM");
-      $this->taskExec("vagrant up")
+      $this->say("In future, run <comment>vagrant up</comment> to boot the VM");
+      $result = $this->taskExec("vagrant up")
         ->dir($this->getConfigValue('repo.root'))
         ->printOutput(TRUE)
         ->run();
+      if (!$result->wasSuccessful()) {
+        $this->logger->error("Drupal VM failed to boot. Read Drupal VM's previous output for more information.");
+        $confirm = $this->confirm("Do you want to try to re-provision the VM? Sometimes this works.", TRUE);
+        if ($confirm) {
+          $result = $this->taskExec("vagrant provision")
+            ->dir($this->getConfigValue('repo.root'))
+            ->printOutput(TRUE)
+            ->run();
+        }
+      }
+      else {
+        $this->yell("Drupal VM booted successfully. Please use vagrant commands to interact with your VM from now on.");
+      }
     }
   }
 
@@ -229,6 +244,11 @@ protected function checkRequirements() {
         $this->logger->warning("The vagrant-hostsupdater plugin is not installed! Attempting to install it...");
         $this->taskExec("vagrant plugin install vagrant-hostsupdater")->run();
       }
+      $vagrant_exec_plugin_installed = (bool) $this->taskExec("vagrant plugin list | grep vagrant-exec")->run()->getOutputData();
+      if ($vagrant_exec_plugin_installed) {
+        $this->logger->warning("The vagrant-exec plugin is not installed! Attempting to install it...");
+        $this->taskExec("vagrant plugin install vagrant-exec")->run();
+      }
     }
   }
 
diff --git a/src/Robo/Common/Executor.php b/src/Robo/Common/Executor.php
index 63c91c4bb..79217eaab 100644
--- a/src/Robo/Common/Executor.php
+++ b/src/Robo/Common/Executor.php
@@ -76,7 +76,8 @@ public function drush($command) {
     // @todo Set to silent if verbosity is less than very verbose.
     $bin = $this->getConfigValue('composer.bin');
     /** @var \Robo\Common\ProcessExecutor $process_executor */
-    $process_executor = Robo::process(new Process("$bin/drush $command"));
+    $drush_alias = $this->getConfigValue('drush.alias');
+    $process_executor = Robo::process(new Process("$bin/drush @$drush_alias $command"));
     return $process_executor->dir($this->getConfigValue('docroot'))
       ->interactive(FALSE)
       ->printOutput(FALSE)
diff --git a/src/Robo/Inspector/Inspector.php b/src/Robo/Inspector/Inspector.php
index b031dbc6a..602c58419 100644
--- a/src/Robo/Inspector/Inspector.php
+++ b/src/Robo/Inspector/Inspector.php
@@ -224,6 +224,23 @@ public function isDrupalVmLocallyInitialized() {
     return $drush_local_alias == $expected_vm_alias;
   }
 
+  /**
+   * Determines if Drupal VM is booted.
+   *
+   * @return bool
+   *   TRUE if Drupal VM is booted.
+   */
+  public function isDrupalVmBooted() {
+    $result = $this->executor->execute("vagrant status")
+      ->printOutput(FALSE)
+      ->printMetadata(FALSE)
+      ->interactive(FALSE)
+      ->run();
+    $output = $result->getOutputData();
+
+    return !strstr($output, "poweroff");
+  }
+
   /**
    * Determines if the current PHP process is being executed inside VM.
    *