diff --git a/src/__phutil_library_map__.php b/src/__phutil_library_map__.php
--- a/src/__phutil_library_map__.php
+++ b/src/__phutil_library_map__.php
@@ -2524,7 +2524,10 @@
     'PhabricatorFilesConfigOptions' => 'applications/files/config/PhabricatorFilesConfigOptions.php',
     'PhabricatorFilesManagementCatWorkflow' => 'applications/files/management/PhabricatorFilesManagementCatWorkflow.php',
     'PhabricatorFilesManagementCompactWorkflow' => 'applications/files/management/PhabricatorFilesManagementCompactWorkflow.php',
+    'PhabricatorFilesManagementCycleWorkflow' => 'applications/files/management/PhabricatorFilesManagementCycleWorkflow.php',
+    'PhabricatorFilesManagementEncodeWorkflow' => 'applications/files/management/PhabricatorFilesManagementEncodeWorkflow.php',
     'PhabricatorFilesManagementEnginesWorkflow' => 'applications/files/management/PhabricatorFilesManagementEnginesWorkflow.php',
+    'PhabricatorFilesManagementGenerateKeyWorkflow' => 'applications/files/management/PhabricatorFilesManagementGenerateKeyWorkflow.php',
     'PhabricatorFilesManagementMigrateWorkflow' => 'applications/files/management/PhabricatorFilesManagementMigrateWorkflow.php',
     'PhabricatorFilesManagementPurgeWorkflow' => 'applications/files/management/PhabricatorFilesManagementPurgeWorkflow.php',
     'PhabricatorFilesManagementRebuildWorkflow' => 'applications/files/management/PhabricatorFilesManagementRebuildWorkflow.php',
@@ -2627,6 +2630,8 @@
     'PhabricatorJiraIssueHasObjectEdgeType' => 'applications/doorkeeper/edge/PhabricatorJiraIssueHasObjectEdgeType.php',
     'PhabricatorJumpNavHandler' => 'applications/search/engine/PhabricatorJumpNavHandler.php',
     'PhabricatorKeyValueDatabaseCache' => 'applications/cache/PhabricatorKeyValueDatabaseCache.php',
+    'PhabricatorKeyring' => 'applications/files/keyring/PhabricatorKeyring.php',
+    'PhabricatorKeyringConfigOptionType' => 'applications/files/keyring/PhabricatorKeyringConfigOptionType.php',
     'PhabricatorLDAPAuthProvider' => 'applications/auth/provider/PhabricatorLDAPAuthProvider.php',
     'PhabricatorLegalpadApplication' => 'applications/legalpad/application/PhabricatorLegalpadApplication.php',
     'PhabricatorLegalpadConfigOptions' => 'applications/legalpad/config/PhabricatorLegalpadConfigOptions.php',
@@ -7173,7 +7178,10 @@
     'PhabricatorFilesConfigOptions' => 'PhabricatorApplicationConfigOptions',
     'PhabricatorFilesManagementCatWorkflow' => 'PhabricatorFilesManagementWorkflow',
     'PhabricatorFilesManagementCompactWorkflow' => 'PhabricatorFilesManagementWorkflow',
+    'PhabricatorFilesManagementCycleWorkflow' => 'PhabricatorFilesManagementWorkflow',
+    'PhabricatorFilesManagementEncodeWorkflow' => 'PhabricatorFilesManagementWorkflow',
     'PhabricatorFilesManagementEnginesWorkflow' => 'PhabricatorFilesManagementWorkflow',
+    'PhabricatorFilesManagementGenerateKeyWorkflow' => 'PhabricatorFilesManagementWorkflow',
     'PhabricatorFilesManagementMigrateWorkflow' => 'PhabricatorFilesManagementWorkflow',
     'PhabricatorFilesManagementPurgeWorkflow' => 'PhabricatorFilesManagementWorkflow',
     'PhabricatorFilesManagementRebuildWorkflow' => 'PhabricatorFilesManagementWorkflow',
@@ -7283,6 +7291,8 @@
     'PhabricatorJiraIssueHasObjectEdgeType' => 'PhabricatorEdgeType',
     'PhabricatorJumpNavHandler' => 'Phobject',
     'PhabricatorKeyValueDatabaseCache' => 'PhutilKeyValueCache',
+    'PhabricatorKeyring' => 'Phobject',
+    'PhabricatorKeyringConfigOptionType' => 'PhabricatorConfigJSONOptionType',
     'PhabricatorLDAPAuthProvider' => 'PhabricatorAuthProvider',
     'PhabricatorLegalpadApplication' => 'PhabricatorApplication',
     'PhabricatorLegalpadConfigOptions' => 'PhabricatorApplicationConfigOptions',
diff --git a/src/applications/config/option/PhabricatorSecurityConfigOptions.php b/src/applications/config/option/PhabricatorSecurityConfigOptions.php
--- a/src/applications/config/option/PhabricatorSecurityConfigOptions.php
+++ b/src/applications/config/option/PhabricatorSecurityConfigOptions.php
@@ -43,6 +43,14 @@
       '255.255.255.255/32',
     );
 
+    $keyring_type = 'custom:PhabricatorKeyringConfigOptionType';
+    $keyring_description = $this->deformat(pht(<<<EOTEXT
+The keyring stores master encryption keys. For help with configuring a keyring
+and encryption, see **[[ %s | Configuring Encryption ]]**.
+EOTEXT
+      ,
+      PhabricatorEnv::getDoclink('Configuring Encryption')));
+
     return array(
       $this->newOption('security.alternate-file-domain', 'string', null)
         ->setLocked(true)
@@ -276,6 +284,10 @@
               'unsecured content over plain HTTP. It is very difficult to '.
               'undo this change once users\' browsers have accepted the '.
               'setting.')),
+        $this->newOption('keyring', $keyring_type, array())
+          ->setHidden(true)
+          ->setSummary(pht('Configure master encryption keys.'))
+          ->setDescription($keyring_description),
     );
   }
 
diff --git a/src/applications/files/format/PhabricatorFileAES256StorageFormat.php b/src/applications/files/format/PhabricatorFileAES256StorageFormat.php
--- a/src/applications/files/format/PhabricatorFileAES256StorageFormat.php
+++ b/src/applications/files/format/PhabricatorFileAES256StorageFormat.php
@@ -9,12 +9,31 @@
   const FORMATKEY = 'aes-256-cbc';
 
   private $keyName;
-  private static $keyRing = array();
 
   public function getStorageFormatName() {
     return pht('Encrypted (AES-256-CBC)');
   }
 
+  public function canGenerateNewKeyMaterial() {
+    return true;
+  }
+
+  public function generateNewKeyMaterial() {
+    $envelope = self::newAES256Key();
+    $material = $envelope->openEnvelope();
+    return base64_encode($material);
+  }
+
+  public function canCycleMasterKey() {
+    return true;
+  }
+
+  public function cycleStorageProperties() {
+    $file = $this->getFile();
+    list($key, $iv) = $this->extractKeyAndIV($file);
+    return $this->formatStorageProperties($key, $iv);
+  }
+
   public function newReadIterator($raw_iterator) {
     $file = $this->getFile();
     $data = $file->loadDataFromIterator($raw_iterator);
@@ -42,6 +61,13 @@
     $key_envelope = self::newAES256Key();
     $iv_envelope = self::newAES256IV();
 
+    return $this->formatStorageProperties($key_envelope, $iv_envelope);
+  }
+
+  private function formatStorageProperties(
+    PhutilOpaqueEnvelope $key_envelope,
+    PhutilOpaqueEnvelope $iv_envelope) {
+
     // Encode the raw binary data with base64 so we can wrap it in JSON.
     $data = array(
       'iv.base64' => base64_encode($iv_envelope->openEnvelope()),
@@ -54,7 +80,7 @@
     // Encrypt the block key with the master key, using a unique IV.
     $data_iv = self::newAES256IV();
     $key_name = $this->getMasterKeyName();
-    $master_key = self::getMasterKeyFromKeyRing($key_name);
+    $master_key = $this->getMasterKeyMaterial($key_name);
     $data_cipher = $this->encryptData($data_clear, $master_key, $data_iv);
 
     return array(
@@ -73,7 +99,7 @@
     $outer_payload = base64_decode($outer_payload);
 
     $outer_key_name = $file->getStorageProperty('key.name');
-    $outer_key = self::getMasterKeyFromKeyRing($outer_key_name);
+    $outer_key = $this->getMasterKeyMaterial($outer_key_name);
 
     $payload = $this->decryptData($outer_payload, $outer_key, $outer_iv);
     $payload = phutil_json_decode($payload);
@@ -142,35 +168,32 @@
     return new PhutilOpaqueEnvelope($iv);
   }
 
-  public function selectKey($key_name) {
+  public function selectMasterKey($key_name) {
     // Require that the key exist on the key ring.
-    self::getMasterKeyFromKeyRing($key_name);
+    $this->getMasterKeyMaterial($key_name);
 
     $this->keyName = $key_name;
     return $this;
   }
 
-  public static function addKeyToKeyRing($name, PhutilOpaqueEnvelope $key) {
-    self::$keyRing[$name] = $key;
-  }
-
   private function getMasterKeyName() {
-    if ($this->keyName === null) {
-      throw new Exception(pht('No master key selected for AES256 storage.'));
+    if ($this->keyName !== null) {
+      return $this->keyName;
     }
 
-    return $this->keyName;
-  }
-
-  private static function getMasterKeyFromKeyRing($key_name) {
-    if (!isset(self::$keyRing[$key_name])) {
-      throw new Exception(
-        pht(
-          'No master key "%s" exists in key ring for AES256 storage.',
-          $key_name));
+    $default = PhabricatorKeyring::getDefaultKeyName(self::FORMATKEY);
+    if ($default !== null) {
+      return $default;
     }
 
-    return self::$keyRing[$key_name];
+    throw new Exception(
+      pht(
+        'No AES256 key is specified in the keyring as a default encryption '.
+        'key, and no encryption key has been explicitly selected.'));
+  }
+
+  private function getMasterKeyMaterial($key_name) {
+    return PhabricatorKeyring::getKey($key_name, self::FORMATKEY);
   }
 
 }
diff --git a/src/applications/files/format/PhabricatorFileStorageFormat.php b/src/applications/files/format/PhabricatorFileStorageFormat.php
--- a/src/applications/files/format/PhabricatorFileStorageFormat.php
+++ b/src/applications/files/format/PhabricatorFileStorageFormat.php
@@ -26,6 +26,29 @@
     return array();
   }
 
+  public function canGenerateNewKeyMaterial() {
+    return false;
+  }
+
+  public function generateNewKeyMaterial() {
+    throw new PhutilMethodNotImplementedException();
+  }
+
+  public function canCycleMasterKey() {
+    return false;
+  }
+
+  public function cycleStorageProperties() {
+    throw new PhutilMethodNotImplementedException();
+  }
+
+  public function selectMasterKey($key_name) {
+    throw new Exception(
+      pht(
+        'This storage format ("%s") does not support key selection.',
+        $this->getStorageFormatName()));
+  }
+
   final public function getStorageFormatKey() {
     return $this->getPhobjectClassConstant('FORMATKEY');
   }
diff --git a/src/applications/files/format/__tests__/PhabricatorFileStorageFormatTestCase.php b/src/applications/files/format/__tests__/PhabricatorFileStorageFormatTestCase.php
--- a/src/applications/files/format/__tests__/PhabricatorFileStorageFormatTestCase.php
+++ b/src/applications/files/format/__tests__/PhabricatorFileStorageFormatTestCase.php
@@ -39,12 +39,17 @@
     $engine = new PhabricatorTestStorageEngine();
 
     $key_name = 'test.abcd';
-    $key_text = new PhutilOpaqueEnvelope('abcdefghijklmnopABCDEFGHIJKLMNOP');
+    $key_text = 'abcdefghijklmnopABCDEFGHIJKLMNOP';
 
-    PhabricatorFileAES256StorageFormat::addKeyToKeyRing($key_name, $key_text);
+    PhabricatorKeyring::addKey(
+      array(
+        'name' => $key_name,
+        'type' => 'aes-256-cbc',
+        'material.base64' => base64_encode($key_text),
+      ));
 
     $format = id(new PhabricatorFileAES256StorageFormat())
-      ->selectKey($key_name);
+      ->selectMasterKey($key_name);
 
     $data = 'The cow jumped over the full moon.';
 
diff --git a/src/applications/files/keyring/PhabricatorKeyring.php b/src/applications/files/keyring/PhabricatorKeyring.php
new file mode 100644
--- /dev/null
+++ b/src/applications/files/keyring/PhabricatorKeyring.php
@@ -0,0 +1,52 @@
+<?php
+
+final class PhabricatorKeyring extends Phobject {
+
+  private static $hasReadConfiguration;
+  private static $keyRing = array();
+
+  public static function addKey($spec) {
+    self::$keyRing[$spec['name']] = $spec;
+  }
+
+  public static function getKey($name, $type) {
+    self::readConfiguration();
+
+    if (empty(self::$keyRing[$name])) {
+      throw new Exception(
+        pht(
+          'No key "%s" exists in keyring.',
+          $name));
+    }
+
+    $spec = self::$keyRing[$name];
+
+    $material = base64_decode($spec['material.base64'], true);
+    return new PhutilOpaqueEnvelope($material);
+  }
+
+  public static function getDefaultKeyName($type) {
+    self::readConfiguration();
+
+    foreach (self::$keyRing as $name => $key) {
+      if (!empty($key['default'])) {
+        return $name;
+      }
+    }
+
+    return null;
+  }
+
+  private static function readConfiguration() {
+    if (self::$hasReadConfiguration) {
+      return true;
+    }
+
+    self::$hasReadConfiguration = true;
+
+    foreach (PhabricatorEnv::getEnvConfig('keyring') as $spec) {
+      self::addKey($spec);
+    }
+  }
+
+}
diff --git a/src/applications/files/keyring/PhabricatorKeyringConfigOptionType.php b/src/applications/files/keyring/PhabricatorKeyringConfigOptionType.php
new file mode 100644
--- /dev/null
+++ b/src/applications/files/keyring/PhabricatorKeyringConfigOptionType.php
@@ -0,0 +1,111 @@
+<?php
+
+final class PhabricatorKeyringConfigOptionType
+  extends PhabricatorConfigJSONOptionType {
+
+  public function validateOption(PhabricatorConfigOption $option, $value) {
+    if (!is_array($value)) {
+      throw new Exception(
+        pht(
+          'Keyring configuration is not valid: value must be a '.
+          'list of encryption keys.'));
+    }
+
+    foreach ($value as $index => $spec) {
+      if (!is_array($spec)) {
+        throw new Exception(
+          pht(
+            'Keyring configuration is not valid: each entry in the list must '.
+            'be a dictionary describing an encryption key, but the value '.
+            'with index "%s" is not a dictionary.',
+            $index));
+      }
+    }
+
+
+    $map = array();
+    $defaults = array();
+    foreach ($value as $index => $spec) {
+      try {
+        PhutilTypeSpec::checkMap(
+          $spec,
+          array(
+            'name' => 'string',
+            'type' => 'string',
+            'material.base64' => 'string',
+            'default' => 'optional bool',
+          ));
+      } catch (Exception $ex) {
+        throw new Exception(
+          pht(
+            'Keyring configuration has an invalid key specification (at '.
+            'index "%s"): %s.',
+            $index,
+            $ex->getMessage()));
+      }
+
+      $name = $spec['name'];
+      if (isset($map[$name])) {
+        throw new Exception(
+          pht(
+            'Keyring configuration is invalid: it describes multiple keys '.
+            'with the same name ("%s"). Each key must have a unique name.',
+            $name));
+      }
+      $map[$name] = true;
+
+      if (idx($spec, 'default')) {
+        $defaults[] = $name;
+      }
+
+      $type = $spec['type'];
+      switch ($type) {
+        case 'aes-256-cbc':
+          if (!function_exists('openssl_encrypt')) {
+            throw new Exception(
+              pht(
+                'Keyring is configured with a "%s" key, but the PHP OpenSSL '.
+                'extension is not installed. Install the OpenSSL extension '.
+                'to enable encryption.',
+                $type));
+          }
+
+          $material = $spec['material.base64'];
+          $material = base64_decode($material, true);
+          if ($material === false) {
+            throw new Exception(
+              pht(
+                'Keyring specifies an invalid key ("%s"): key material '.
+                'should be base64 encoded.',
+                $name));
+          }
+
+          if (strlen($material) != 32) {
+            throw new Exception(
+              pht(
+                'Keyring specifies an invalid key ("%s"): key material '.
+                'should be 32 bytes (256 bits) but has length %s.',
+                $name,
+                new PhutilNumber(strlen($material))));
+          }
+          break;
+        default:
+          throw new Exception(
+            pht(
+              'Keyring configuration is invalid: it describes a key with '.
+              'type "%s", but this type is unknown.',
+              $type));
+      }
+    }
+
+    if (count($defaults) > 1) {
+      throw new Exception(
+        pht(
+          'Keyring configuration is invalid: it describes multiple default '.
+          'encryption keys. No more than one key may be the default key. '.
+          'Keys currently configured as defaults: %s.',
+          implode(', ', $defaults)));
+    }
+  }
+
+}
diff --git a/src/applications/files/management/PhabricatorFilesManagementCycleWorkflow.php b/src/applications/files/management/PhabricatorFilesManagementCycleWorkflow.php
new file mode 100644
--- /dev/null
+++ b/src/applications/files/management/PhabricatorFilesManagementCycleWorkflow.php
@@ -0,0 +1,132 @@
+<?php
+
+final class PhabricatorFilesManagementCycleWorkflow
+  extends PhabricatorFilesManagementWorkflow {
+
+  protected function didConstruct() {
+    $this
+      ->setName('cycle')
+      ->setSynopsis(
+        pht('Cycle master key for encrypted files.'))
+      ->setArguments(
+        array(
+          array(
+            'name' => 'key',
+            'param' => 'keyname',
+            'help' => pht('Select a specific storage key to cycle to.'),
+          ),
+          array(
+            'name' => 'all',
+            'help' => pht('Change encoding for all files.'),
+          ),
+          array(
+            'name' => 'names',
+            'wildcard' => true,
+          ),
+        ));
+  }
+
+  public function execute(PhutilArgumentParser $args) {
+    $iterator = $this->buildIterator($args);
+    if (!$iterator) {
+      throw new PhutilArgumentUsageException(
+        pht(
+          'Either specify a list of files to cycle, or use --all to cycle '.
+          'all files.'));
+    }
+
+    $format_map = PhabricatorFileStorageFormat::getAllFormats();
+    $engines = PhabricatorFileStorageEngine::loadAllEngines();
+
+    $key_name = $args->getArg('key');
+
+    $failed = array();
+    foreach ($iterator as $file) {
+      $monogram = $file->getMonogram();
+
+      $engine_key = $file->getStorageEngine();
+      $engine = idx($engines, $engine_key);
+
+      if (!$engine) {
+        echo tsprintf(
+          "%s\n",
+          pht(
+            '%s: Uses unknown storage engine "%s".',
+            $monogram,
+            $engine_key));
+        $failed[] = $file;
+        continue;
+      }
+
+      if ($engine->isChunkEngine()) {
+        echo tsprintf(
+          "%s\n",
+          pht(
+            '%s: Stored as chunks, declining to cycle directly.',
+            $monogram));
+        continue;
+      }
+
+      $format_key = $file->getStorageFormat();
+      if (empty($format_map[$format_key])) {
+        echo tsprintf(
+          "%s\n",
+          pht(
+            '%s: Uses unknown storage format "%s".',
+            $monogram,
+            $format_key));
+        $failed[] = $file;
+        continue;
+      }
+
+      $format = clone $format_map[$format_key];
+      $format->setFile($file);
+
+      if (!$format->canCycleMasterKey()) {
+        echo tsprintf(
+          "%s\n",
+          pht(
+            '%s: Storage format ("%s") does not support key cycling.',
+            $monogram,
+            $format->getStorageFormatName()));
+        continue;
+      }
+
+      echo tsprintf(
+        "%s\n",
+        pht(
+          '%s: Cycling master key.',
+          $monogram));
+
+      try {
+        if ($key_name) {
+          $format->selectMasterKey($key_name);
+        }
+
+        $file->cycleMasterStorageKey($format);
+
+        echo tsprintf(
+          "%s\n",
+          pht('Done.'));
+      } catch (Exception $ex) {
+        echo tsprintf(
+          "%B\n",
+          pht('Failed! %s', (string)$ex));
+        $failed[] = $file;
+      }
+    }
+
+    if ($failed) {
+      $monograms = mpull($failed, 'getMonogram');
+
+      echo tsprintf(
+        "%s\n",
+        pht('Failures: %s.', implode(', ', $monograms)));
+
+      return 1;
+    }
+
+    return 0;
+  }
+
+}
diff --git a/src/applications/files/management/PhabricatorFilesManagementEncodeWorkflow.php b/src/applications/files/management/PhabricatorFilesManagementEncodeWorkflow.php
new file mode 100644
--- /dev/null
+++ b/src/applications/files/management/PhabricatorFilesManagementEncodeWorkflow.php
@@ -0,0 +1,151 @@
+<?php
+
+final class PhabricatorFilesManagementEncodeWorkflow
+  extends PhabricatorFilesManagementWorkflow {
+
+  protected function didConstruct() {
+    $this
+      ->setName('encode')
+      ->setSynopsis(
+        pht('Change the storage encoding of files.'))
+      ->setArguments(
+        array(
+          array(
+            'name' => 'as',
+            'param' => 'format',
+            'help' => pht('Select the storage format to use.'),
+          ),
+          array(
+            'name' => 'key',
+            'param' => 'keyname',
+            'help' => pht('Select a specific storage key.'),
+          ),
+          array(
+            'name' => 'all',
+            'help' => pht('Change encoding for all files.'),
+          ),
+          array(
+            'name' => 'force',
+            'help' => pht(
+              'Re-encode files which are already stored in the target '.
+              'encoding.'),
+          ),
+          array(
+            'name' => 'names',
+            'wildcard' => true,
+          ),
+        ));
+  }
+
+  public function execute(PhutilArgumentParser $args) {
+    $iterator = $this->buildIterator($args);
+    if (!$iterator) {
+      throw new PhutilArgumentUsageException(
+        pht(
+          'Either specify a list of files to encode, or use --all to '.
+          'encode all files.'));
+    }
+
+    $force = (bool)$args->getArg('force');
+
+    $format_list = PhabricatorFileStorageFormat::getAllFormats();
+    $format_list = array_keys($format_list);
+    $format_list = implode(', ', $format_list);
+
+    $format_key = $args->getArg('as');
+    if (!strlen($format_key)) {
+      throw new PhutilArgumentUsageException(
+        pht(
+          'Use --as <format> to select a target encoding format. Available '.
+          'formats are: %s.',
+          $format_list));
+    }
+
+    $format = PhabricatorFileStorageFormat::getFormat($format_key);
+    if (!$format) {
+      throw new PhutilArgumentUsageException(
+        pht(
+          'Storage format "%s" is not valid. Available formats are: %s.',
+          $format_key,
+          $format_list));
+    }
+
+    $key_name = $args->getArg('key');
+    if (strlen($key_name)) {
+      $format->selectMasterKey($key_name);
+    }
+
+    $engines = PhabricatorFileStorageEngine::loadAllEngines();
+
+    $failed = array();
+    foreach ($iterator as $file) {
+      $monogram = $file->getMonogram();
+
+      $engine_key = $file->getStorageEngine();
+      $engine = idx($engines, $engine_key);
+
+      if (!$engine) {
+        echo tsprintf(
+          "%s\n",
+          pht(
+            '%s: Uses unknown storage engine "%s".',
+            $monogram,
+            $engine_key));
+        $failed[] = $file;
+        continue;
+      }
+
+      if ($engine->isChunkEngine()) {
+        echo tsprintf(
+          "%s\n",
+          pht(
+            '%s: Stored as chunks, no data to encode directly.',
+            $monogram));
+        continue;
+      }
+
+      if (($file->getStorageFormat() == $format_key) && !$force) {
+        echo tsprintf(
+          "%s\n",
+          pht(
+            '%s: Already encoded in target format.',
+            $monogram));
+        continue;
+      }
+
+      echo tsprintf(
+        "%s\n",
+        pht(
+          '%s: Changing encoding from "%s" to "%s".',
+          $monogram,
+          $file->getStorageFormat(),
+          $format_key));
+
+      try {
+        $file->migrateToStorageFormat($format);
+
+        echo tsprintf(
+          "%s\n",
+          pht('Done.'));
+      } catch (Exception $ex) {
+        echo tsprintf(
+          "%B\n",
+          pht('Failed! %s', (string)$ex));
+        $failed[] = $file;
+      }
+    }
+
+    if ($failed) {
+      $monograms = mpull($failed, 'getMonogram');
+
+      echo tsprintf(
+        "%s\n",
+        pht('Failures: %s.', implode(', ', $monograms)));
+
+      return 1;
+    }
+
+    return 0;
+  }
+
+}
diff --git a/src/applications/files/management/PhabricatorFilesManagementGenerateKeyWorkflow.php b/src/applications/files/management/PhabricatorFilesManagementGenerateKeyWorkflow.php
new file mode 100644
--- /dev/null
+++ b/src/applications/files/management/PhabricatorFilesManagementGenerateKeyWorkflow.php
@@ -0,0 +1,63 @@
+<?php
+
+final class PhabricatorFilesManagementGenerateKeyWorkflow
+  extends PhabricatorFilesManagementWorkflow {
+
+  protected function didConstruct() {
+    $this
+      ->setName('generate-key')
+      ->setSynopsis(
+        pht('Generate an encryption key.'))
+      ->setArguments(
+        array(
+          array(
+            'name' => 'type',
+            'param' => 'keytype',
+            'help' => pht('Select the type of key to generate.'),
+          ),
+        ));
+  }
+
+  public function execute(PhutilArgumentParser $args) {
+    $type = $args->getArg('type');
+    if (!strlen($type)) {
+      throw new PhutilArgumentUsageException(
+        pht(
+          'Specify the type of key to generate with --type.'));
+    }
+
+    $format = PhabricatorFileStorageFormat::getFormat($type);
+    if (!$format) {
+      throw new PhutilArgumentUsageException(
+        pht(
+          'No key type "%s" exists.',
+          $type));
+    }
+
+    if (!$format->canGenerateNewKeyMaterial()) {
+      throw new PhutilArgumentUsageException(
+        pht(
+          'Storage format "%s" can not generate keys.',
+          $format->getStorageFormatName()));
+    }
+
+    $material = $format->generateNewKeyMaterial();
+
+    $structure = array(
+      'name' => 'generated-key-'.Filesystem::readRandomCharacters(12),
+      'type' => $type,
+      'material.base64' => $material,
+    );
+
+    $json = id(new PhutilJSON())->encodeFormatted($structure);
+
+    echo tsprintf(
+      "%s: %s\n\n%B\n",
+      pht('Key Material'),
+      $format->getStorageFormatName(),
+      $json);
+
+    return 0;
+  }
+
+}
diff --git a/src/applications/files/storage/PhabricatorFile.php b/src/applications/files/storage/PhabricatorFile.php
--- a/src/applications/files/storage/PhabricatorFile.php
+++ b/src/applications/files/storage/PhabricatorFile.php
@@ -326,7 +326,12 @@
 
     $file = self::initializeNewFile();
 
-    $default_key = PhabricatorFileRawStorageFormat::FORMATKEY;
+    $has_aes = PhabricatorKeyring::getDefaultKeyName();
+    if ($has_aes !== null) {
+      $default_key = PhabricatorFileAES256StorageFormat::FORMATKEY;
+    } else {
+      $default_key = PhabricatorFileRawStorageFormat::FORMATKEY;
+    }
     $key = idx($params, 'format', $default_key);
 
     // Callers can pass in an object explicitly instead of a key. This is
@@ -444,6 +449,53 @@
     return $this;
   }
 
+  public function migrateToStorageFormat(PhabricatorFileStorageFormat $format) {
+    if (!$this->getID() || !$this->getStorageHandle()) {
+      throw new Exception(
+        pht("You can not migrate a file which hasn't yet been saved."));
+    }
+
+    $data = $this->loadFileData();
+    $params = array(
+      'name' => $this->getName(),
+    );
+
+    $engine = $this->instantiateStorageEngine();
+    $old_handle = $this->getStorageHandle();
+
+    $properties = $format->newStorageProperties();
+    $this->setStorageFormat($format->getStorageFormatKey());
+    $this->setStorageProperties($properties);
+
+    list($identifier, $new_handle) = $this->writeToEngine(
+      $engine,
+      $data,
+      $params);
+
+    $this->setStorageHandle($new_handle);
+    $this->save();
+
+    $this->deleteFileDataIfUnused(
+      $engine,
+      $identifier,
+      $old_handle);
+
+    return $this;
+  }
+
+  public function cycleMasterStorageKey(PhabricatorFileStorageFormat $format) {
+    if (!$this->getID() || !$this->getStorageHandle()) {
+      throw new Exception(
+        pht("You can not cycle keys for a file which hasn't yet been saved."));
+    }
+
+    $properties = $format->cycleStorageProperties();
+    $this->setStorageProperties($properties);
+    $this->save();
+
+    return $this;
+  }
+
   private function writeToEngine(
     PhabricatorFileStorageEngine $engine,
     $data,
diff --git a/src/docs/user/configuration/configuring_encryption.diviner b/src/docs/user/configuration/configuring_encryption.diviner
new file mode 100644
--- /dev/null
+++ b/src/docs/user/configuration/configuring_encryption.diviner
@@ -0,0 +1,196 @@
+@title Configuring Encryption
+@group config
+
+Setup guide for configuring encryption.
+
+Overview
+========
+
+Phabricator supports at-rest encryption of uploaded file data stored in the
+"Files" application.
+
+Configuring at-rest file data encryption does not encrypt any other data or
+resources. In particular, it does not encrypt the database and does not encrypt
+Passphrase credentials.
+
+Attackers who compromise a Phabricator host can read the master key and decrypt
+the data. In most configurations, this does not represent a significant
+barrier above and beyond accessing the file data. Thus, configuring at-rest
+encryption is primarily useful for two types of installs:
+
+  - If you maintain your own webserver and database hardware but want to use
+    Amazon S3 or a similar cloud provider as a blind storage server, file data
+    encryption can let you do so without needing to trust the cloud provider.
+  - If you face a regulatory or compliance need to encrypt data at rest but do
+    not need to actually secure this data, encrypting the data and placing the
+    master key in plaintext next to it may satisfy compliance requirements.
+
+The remainder of this document discusses how to configure at-rest encryption.
+
+
+Quick Start
+===========
+
+To configure encryption, you will generally follow these steps:
+
+  - Generate a master key with `bin/files generate-key`.
+  - Add the master key it to the `keyring`, but don't mark it as `default` yet.
+  - Use `bin/files encode ...` to test encrypting a few files.
+  - Mark the key as `default` to automatically encrypt new files.
+  - Use `bin/files encode --all ...` to encrypt any existing files.
+
+See the following sections for detailed guidance on these steps.
+
+
+Configuring a Keyring
+=====================
+
+To configure a keyring, set `keyring` with `bin/config` or by using another
+configuration source. This option should be a list of keys in this format:
+
+```lang=json
+...
+"keyring": [
+  {
+    "name": "master.key",
+    "type": "aes-256-cbc",
+    "material.base64": "UcHUJqq8MhZRwhvDV8sJwHj7bNJoM4tWfOIi..."
+    "default": true
+  },
+  ...
+]
+...
+```
+
+Each key should have these properties:
+
+  - `name`: //Required string.// A unique key name.
+  - `type`: //Required string.// Type of the key. Only `aes-256-cbc` is
+    supported.
+  - `material.base64`: //Required string.// The key material. See below for
+    details.
+  - `default`: //Optional bool.// Optionally, mark exactly one key as the
+    default key to enable encryption of newly uploaded file data.
+
+The key material is sensitive an an attacker who learns it can decrypt data
+from the storage engine.
+
+
+Format: Raw Data
+================
+
+The `raw` storage format is automatically selected for all newly uploaded
+file data if no key is makred as the `default` key in the keyring. This is
+the behavior of Phabricator if you haven't configured anything.
+
+This format stores raw data without modification.
+
+
+Format: AES256
+==============
+
+The `aes-256-cbc` storage format is automatically selected for all newly
+uploaded file data if an AES256 key is marked as the `default` key in the
+keyring.
+
+This format uses AES256 in CBC mode. Each block of file data is encrypted with
+a unique, randomly generated private key. That key is the encrypted with the
+master key. Among other motivations, this strategy allows the master key to be
+cycled relatively cheaply later (see "Cycling Master Keys" below).
+
+AES256 keys should be randomly generated and 256 bits (32 characters) in
+length, then base64 encoded when represented in `keyring`.
+
+You can generate a valid, properly encoded AES256 master key with this command:
+
+```
+phabricator/ $ ./bin/files generate-key --type aes-256-cbc
+```
+
+This mode is generally similar to the default server-side encryption mode
+supported by Amazon S3.
+
+
+Format: ROT13
+=============
+
+The `rot13` format is a test format that is never selected by default. You can
+select this format explicitly with `bin/files encode` to test storage and
+encryption behavior.
+
+This format applies ROT13 encoding to file data.
+
+
+Changing File Storage Formats
+=============================
+
+To test configuration, you can explicitly change the storage format of a file.
+
+This will read the file data, decrypt it if necessary, write a new copy of the
+data with the desired encryption, then update the file to point at the new
+data. You can use this to make sure encryption works before turning it on by
+default.
+
+To change the format of an individual file, run this command:
+
+```
+phabricator/ $ ./bin/files encode --as <format> F123 [--key <key>]
+```
+
+This will change the storage format of the sepcified file.
+
+
+Verifying Storage Formats
+=========================
+
+You can review the storage format of a file from the web UI, in the
+{nav Storage} tab under "Format". You can also use the "Engine" and "Handle"
+properties to identify where the underlying data is stored and verify that
+it is encrypted or encoded in the way you expect.
+
+See @{article:Configuring File Storage} for more information on storage
+engines.
+
+
+Cycling Master Keys
+===================
+
+If you need to cycle your master key, some storage formats support key cycling.
+
+Cycling a file's encryption key decodes the local key for the data using the
+old master key, then re-encodes it using the new master key. This is primarily
+useful if you believe your master key may have been compromised.
+
+First, add a new key to the keyring and mark it as the default key. You need
+to leave the old key in place for now so existing data can be decrypted.
+
+To cycle an individual file, run this command:
+
+```
+phabricator/ $ ./bin/files cycle F123
+```
+
+Verify that cycling worked properly by examining the command output and
+accessing the file to check that the data is present and decryptable. You
+can cycle additional files to gain additional confidence.
+
+You can cycle all files with this command:
+
+```
+phabricator/ $ ./bin/files cycle --all
+```
+
+Once all files have been cycled, remove the old master key from the keyring.
+
+Not all storage formats support key cycling: cycling a file only has an effect
+if the storage format is an encrypted format. For example, cycling a file that
+uses the `raw` storage format has no effect.
+
+
+Next Steps
+==========
+
+Continue by:
+
+  - understanding storage engines with @{article:Configuring File Storage}; or
+  - returning to the @{article:Configuration Guide}.
diff --git a/src/docs/user/configuration/configuring_file_storage.diviner b/src/docs/user/configuration/configuring_file_storage.diviner
--- a/src/docs/user/configuration/configuring_file_storage.diviner
+++ b/src/docs/user/configuration/configuring_file_storage.diviner
@@ -197,4 +197,6 @@
 
 Continue by:
 
+  - reviewing at-rest encryption options with
+    @{article:Configuring Encryption}; or
   - returning to the @{article:Configuration Guide}.