diff --git a/admin/tool/dataprivacy/classes/api.php b/admin/tool/dataprivacy/classes/api.php
index e73a34c0e79..10889a915ec 100644
--- a/admin/tool/dataprivacy/classes/api.php
+++ b/admin/tool/dataprivacy/classes/api.php
@@ -227,25 +227,24 @@ class api {
      * @param int $foruser The user whom the request is being made for.
      * @param int $type The request type.
      * @param string $comments Request comments.
+     * @param int $creationmethod The creation method of the data request.
      * @return data_request
      * @throws invalid_persistent_exception
      * @throws coding_exception
      */
-    public static function create_data_request($foruser, $type, $comments = '') {
-        global $USER;
+    public static function create_data_request($foruser, $type, $comments = '',
+                                               $creationmethod = data_request::DATAREQUEST_CREATION_MANUAL) {
+        global $USER, $ADMIN;
 
         $datarequest = new data_request();
         // The user the request is being made for.
         $datarequest->set('userid', $foruser);
 
-        $requestinguser = $USER->id;
-        // Check when the user is making a request on behalf of another.
-        if ($requestinguser != $foruser) {
-            if (self::is_site_dpo($requestinguser)) {
-                // The user making the request is a DPO. Should be fine.
-                $datarequest->set('dpo', $requestinguser);
-            }
-        }
+        // The cron is considered to be a guest user when it creates a data request.
+        // NOTE: This should probably be changed. We should leave the default value for $requestinguser if
+        // the request is not explicitly created by a specific user.
+        $requestinguser = (isguestuser() && $creationmethod == data_request::DATAREQUEST_CREATION_AUTO) ?
+                $ADMIN->id : $USER->id;
         // The user making the request.
         $datarequest->set('requestedby', $requestinguser);
         // Set status.
diff --git a/admin/tool/dataprivacy/classes/data_request.php b/admin/tool/dataprivacy/classes/data_request.php
index 92c8c1ff243..997642261fa 100644
--- a/admin/tool/dataprivacy/classes/data_request.php
+++ b/admin/tool/dataprivacy/classes/data_request.php
@@ -37,6 +37,12 @@ class data_request extends persistent {
     /** The table name this persistent object maps to. */
     const TABLE = 'tool_dataprivacy_request';
 
+    /** Data request created manually. */
+    const DATAREQUEST_CREATION_MANUAL = 0;
+
+    /** Data request created automatically. */
+    const DATAREQUEST_CREATION_AUTO = 1;
+
     /**
      * Return the definition of the properties of this model.
      *
@@ -111,6 +117,14 @@ class data_request extends persistent {
                 'type' => PARAM_INT,
                 'default' => FORMAT_PLAIN
             ],
+            'creationmethod' => [
+                'default' => self::DATAREQUEST_CREATION_MANUAL,
+                'choices' => [
+                    self::DATAREQUEST_CREATION_MANUAL,
+                    self::DATAREQUEST_CREATION_AUTO
+                ],
+                'type' => PARAM_INT
+            ],
         ];
     }
 
diff --git a/admin/tool/dataprivacy/classes/task/delete_existing_deleted_users.php b/admin/tool/dataprivacy/classes/task/delete_existing_deleted_users.php
new file mode 100644
index 00000000000..a0787477ea1
--- /dev/null
+++ b/admin/tool/dataprivacy/classes/task/delete_existing_deleted_users.php
@@ -0,0 +1,88 @@
+<?php
+// This file is part of Moodle - http://moodle.org/
+//
+// Moodle is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Moodle is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Moodle.  If not, see <http://www.gnu.org/licenses/>.
+
+/**
+ * Scheduled task to create delete data request for pre-existing deleted users.
+ *
+ * @package    tool_dataprivacy
+ * @copyright  2018 Mihail Geshoski
+ * @license    http://www.gnu.org/copyleft/gpl.html GNU GPL v3 or later
+ */
+
+namespace tool_dataprivacy\task;
+
+use core\task\scheduled_task;
+use tool_dataprivacy\api;
+use tool_dataprivacy\data_request;
+
+defined('MOODLE_INTERNAL') || die();
+
+require_once($CFG->dirroot . '/' . $CFG->admin . '/tool/dataprivacy/lib.php');
+
+/**
+ * Scheduled task to create delete data request for pre-existing deleted users.
+ *
+ * @package    tool_dataprivacy
+ * @copyright  2018 Mihail Geshoski
+ * @license    http://www.gnu.org/copyleft/gpl.html GNU GPL v3 or later
+ */
+class delete_existing_deleted_users extends scheduled_task {
+
+    /**
+     * Returns the task name.
+     *
+     * @return string
+     */
+    public function get_name() {
+        return get_string('deleteexistingdeleteduserstask', 'tool_dataprivacy');
+    }
+
+    /**
+     * Run the task to delete expired data request files and update request statuses.
+     *
+     */
+    public function execute() {
+        global $DB;
+
+        // Select all deleted users that do not have any delete data requests created for them.
+        $sql = "SELECT DISTINCT(u.id)
+                  FROM {user} u
+             LEFT JOIN {tool_dataprivacy_request} r
+                       ON u.id = r.userid
+                 WHERE u.deleted = ?
+                       AND (r.id IS NULL
+                           OR r.type != ?)";
+
+        $params = [
+            1,
+            api::DATAREQUEST_TYPE_DELETE
+        ];
+
+        $deletedusers = $DB->get_records_sql($sql, $params);
+        $createdrequests = 0;
+
+        foreach ($deletedusers as $user) {
+            api::create_data_request($user->id, api::DATAREQUEST_TYPE_DELETE,
+                    get_string('datarequestcreatedfromscheduledtask', 'tool_dataprivacy'),
+                    data_request::DATAREQUEST_CREATION_AUTO);
+            $createdrequests++;
+        }
+
+        if ($createdrequests > 0) {
+            mtrace($createdrequests . ' delete data request(s) created for existing deleted users');
+        }
+    }
+}
diff --git a/admin/tool/dataprivacy/classes/task/initiate_data_request_task.php b/admin/tool/dataprivacy/classes/task/initiate_data_request_task.php
index 70402f48f4b..d35f9176ef9 100644
--- a/admin/tool/dataprivacy/classes/task/initiate_data_request_task.php
+++ b/admin/tool/dataprivacy/classes/task/initiate_data_request_task.php
@@ -70,27 +70,6 @@ class initiate_data_request_task extends adhoc_task {
             return;
         }
 
-        $requestedby = $datarequest->get('requestedby');
-        $valid = true;
-        $comment = '';
-        $foruser = $datarequest->get('userid');
-        if ($foruser != $requestedby) {
-            if (!$valid = api::can_create_data_request_for_user($foruser, $requestedby)) {
-                $params = (object)[
-                    'requestedby' => $requestedby,
-                    'userid' => $foruser
-                ];
-                $comment = get_string('errornocapabilitytorequestforothers', 'tool_dataprivacy', $params);
-                mtrace($comment);
-            }
-        }
-        // Reject the request outright if it's invalid.
-        if (!$valid) {
-            $dpo = $datarequest->get('dpo');
-            api::update_request_status($requestid, api::DATAREQUEST_STATUS_REJECTED, $dpo, $comment);
-            return;
-        }
-
         // Update the status of this request as pre-processing.
         mtrace('Generating the contexts containing personal data for the user...');
         api::update_request_status($requestid, api::DATAREQUEST_STATUS_PREPROCESSING);
diff --git a/admin/tool/dataprivacy/classes/task/process_data_request_task.php b/admin/tool/dataprivacy/classes/task/process_data_request_task.php
index c44b661d97f..802f61af70d 100644
--- a/admin/tool/dataprivacy/classes/task/process_data_request_task.php
+++ b/admin/tool/dataprivacy/classes/task/process_data_request_task.php
@@ -76,7 +76,6 @@ class process_data_request_task extends adhoc_task {
 
         // Get the user details now. We might not be able to retrieve it later if it's a deletion processing.
         $foruser = core_user::get_user($request->userid);
-        $usercontext = \context_user::instance($foruser->id);
 
         // Update the status of this request as pre-processing.
         mtrace('Processing request...');
@@ -84,6 +83,14 @@ class process_data_request_task extends adhoc_task {
         $completestatus = api::DATAREQUEST_STATUS_COMPLETE;
 
         if ($request->type == api::DATAREQUEST_TYPE_EXPORT) {
+            // Get the user context.
+            $usercontext = \context_user::instance($foruser->id, IGNORE_MISSING);
+            if (!$usercontext) {
+                mtrace("Request {$requestid} cannot be processed due to a missing user context instance for the user
+                    with ID {$foruser->id}. Skipping...");
+                return;
+            }
+
             // Get the collection of approved_contextlist objects needed for core_privacy data export.
             $approvedclcollection = api::get_approved_contextlist_collection_for_request($requestpersistent);
 
@@ -191,12 +198,19 @@ class process_data_request_task extends adhoc_task {
 
         // Send message to the user involved.
         if ($notifyuser) {
+            $messagesent = false;
             if ($emailonly) {
-                email_to_user($foruser, $dpo, $subject, $message->fullmessage, $messagehtml);
+                // Do not sent an email if the user has been deleted. The user email has been previously deleted.
+                if (!$foruser->deleted) {
+                    $messagesent = email_to_user($foruser, $dpo, $subject, $message->fullmessage, $messagehtml);
+                }
             } else {
-                message_send($message);
+                $messagesent = message_send($message);
+            }
+
+            if ($messagesent) {
+                mtrace('Message sent to user: ' . $messagetextdata['username']);
             }
-            mtrace('Message sent to user: ' . $messagetextdata['username']);
         }
 
         // Send to requester as well in some circumstances.
diff --git a/admin/tool/dataprivacy/db/install.xml b/admin/tool/dataprivacy/db/install.xml
index e3402693b8f..2d4a01a9591 100644
--- a/admin/tool/dataprivacy/db/install.xml
+++ b/admin/tool/dataprivacy/db/install.xml
@@ -19,6 +19,7 @@
         <FIELD NAME="usermodified" TYPE="int" LENGTH="10" NOTNULL="true" DEFAULT="0" SEQUENCE="false" COMMENT="The user who created/modified this request object"/>
         <FIELD NAME="timecreated" TYPE="int" LENGTH="10" NOTNULL="true" DEFAULT="0" SEQUENCE="false" COMMENT="The time this data request was created"/>
         <FIELD NAME="timemodified" TYPE="int" LENGTH="10" NOTNULL="true" DEFAULT="0" SEQUENCE="false" COMMENT="The last time this data request was updated"/>
+        <FIELD NAME="creationmethod" TYPE="int" LENGTH="10" NOTNULL="true" DEFAULT="0" SEQUENCE="false" COMMENT="The type of the creation method of the data request"/>
       </FIELDS>
       <KEYS>
         <KEY NAME="primary" TYPE="primary" FIELDS="id"/>
diff --git a/admin/tool/dataprivacy/db/tasks.php b/admin/tool/dataprivacy/db/tasks.php
index 5ee3a19aa17..e3bedd695ab 100644
--- a/admin/tool/dataprivacy/db/tasks.php
+++ b/admin/tool/dataprivacy/db/tasks.php
@@ -50,5 +50,13 @@ $tasks = array(
         'day' => '*',
         'dayofweek' => '*',
         'month' => '*'
+    ), array(
+        'classname' => 'tool_dataprivacy\task\delete_existing_deleted_users',
+        'blocking' => 0,
+        'minute' => 'R',
+        'hour' => 'R',
+        'day' => '*',
+        'dayofweek' => '*',
+        'month' => '*'
     ),
 );
diff --git a/admin/tool/dataprivacy/db/upgrade.php b/admin/tool/dataprivacy/db/upgrade.php
index a5c3d2170b4..1ac5b3358bf 100644
--- a/admin/tool/dataprivacy/db/upgrade.php
+++ b/admin/tool/dataprivacy/db/upgrade.php
@@ -265,5 +265,17 @@ function xmldb_tool_dataprivacy_upgrade($oldversion) {
         upgrade_plugin_savepoint(true, 2017111354, 'tool', 'dataprivacy');
     }
 
+    if ($oldversion < 2017111356) {
+        // Define field sensitivedatareasons to be added to tool_dataprivacy_purpose.
+        $table = new xmldb_table('tool_dataprivacy_request');
+        $field = new xmldb_field('creationmethod', XMLDB_TYPE_INTEGER, 10, null, XMLDB_NOTNULL, null, 0, 'timemodified');
+        // Conditionally launch add field sensitivedatareasons.
+        if (!$dbman->field_exists($table, $field)) {
+            $dbman->add_field($table, $field);
+        }
+        // Dataprivacy savepoint reached.
+        upgrade_plugin_savepoint(true, 2017111356, 'tool', 'dataprivacy');
+    }
+
     return true;
 }
diff --git a/admin/tool/dataprivacy/lang/en/tool_dataprivacy.php b/admin/tool/dataprivacy/lang/en/tool_dataprivacy.php
index 43f4e24dc13..bd426c5d979 100644
--- a/admin/tool/dataprivacy/lang/en/tool_dataprivacy.php
+++ b/admin/tool/dataprivacy/lang/en/tool_dataprivacy.php
@@ -80,6 +80,7 @@ $string['dataregistryinfo'] = 'The data registry enables categories (types of da
 $string['dataretentionexplanation'] = 'This summary shows the default categories and purposes for retaining user data. Certain areas may have more specific categories and purposes than those listed here.';
 $string['dataretentionsummary'] = 'Data retention summary';
 $string['datarequestcreatedforuser'] = 'Data request created for {$a}';
+$string['datarequestcreatedfromscheduledtask'] = 'Automatically created from a scheduled task (pre-existing deleted user).';
 $string['datarequestemailsubject'] = 'Data request: {$a}';
 $string['datarequests'] = 'Data requests';
 $string['datecomment'] = '[{$a->date}]: ' . PHP_EOL . ' {$a->comment}';
@@ -93,6 +94,7 @@ $string['deletedefaults'] = 'Delete defaults: {$a}';
 $string['deletedefaultsconfirmation'] = 'Are you sure you want to delete the default category and purpose for {$a} modules?';
 $string['deleteexpiredcontextstask'] = 'Delete expired contexts';
 $string['deleteexpireddatarequeststask'] = 'Delete expired data request export files';
+$string['deleteexistingdeleteduserstask'] = 'Create delete data request for pre-existing deleted users';
 $string['deletemyaccount'] = 'Delete my account';
 $string['deletepurpose'] = 'Delete purpose';
 $string['deletepurposetext'] = 'Are you sure you want to delete the purpose \'{$a}\'?';
diff --git a/admin/tool/dataprivacy/tests/api_test.php b/admin/tool/dataprivacy/tests/api_test.php
index f0617d9aae5..ec6c171fdba 100644
--- a/admin/tool/dataprivacy/tests/api_test.php
+++ b/admin/tool/dataprivacy/tests/api_test.php
@@ -608,7 +608,6 @@ class tool_dataprivacy_api_testcase extends advanced_testcase {
         $datarequest = api::create_data_request($user->id, api::DATAREQUEST_TYPE_EXPORT, $comment);
         $this->assertEquals($user->id, $datarequest->get('userid'));
         $this->assertEquals($USER->id, $datarequest->get('requestedby'));
-        $this->assertEquals($USER->id, $datarequest->get('dpo'));
         $this->assertEquals(api::DATAREQUEST_TYPE_EXPORT, $datarequest->get('type'));
         $this->assertEquals(api::DATAREQUEST_STATUS_PENDING, $datarequest->get('status'));
         $this->assertEquals($comment, $datarequest->get('comments'));
diff --git a/admin/tool/dataprivacy/version.php b/admin/tool/dataprivacy/version.php
index 689204cd710..04ddf6ec72c 100644
--- a/admin/tool/dataprivacy/version.php
+++ b/admin/tool/dataprivacy/version.php
@@ -24,6 +24,6 @@
 
 defined('MOODLE_INTERNAL') || die;
 
-$plugin->version   = 2017111355;
+$plugin->version   = 2017111356;
 $plugin->requires  = 2017111304.00;        // Moodle 3.4.4 (Build: 20180517) and upwards.
 $plugin->component = 'tool_dataprivacy';