diff --git a/privacy/classes/local/request/moodle_content_writer.php b/privacy/classes/local/request/moodle_content_writer.php
index 1cf0d453cc0..98b330b0f88 100644
--- a/privacy/classes/local/request/moodle_content_writer.php
+++ b/privacy/classes/local/request/moodle_content_writer.php
@@ -159,7 +159,7 @@ class moodle_content_writer implements content_writer {
      * @return  string                      The processed string
      */
     public function rewrite_pluginfile_urls(array $subcontext, $component, $filearea, $itemid, $text) : string {
-        return str_replace('@@PLUGINFILE@@/', 'files/', $text);
+        return str_replace('@@PLUGINFILE@@/', $this->get_files_target_path($component, $filearea, $itemid).'/', $text);
     }
 
     /**
@@ -188,11 +188,12 @@ class moodle_content_writer implements content_writer {
      */
     public function export_file(array $subcontext, \stored_file $file) : content_writer  {
         if (!$file->is_directory()) {
-            $subcontextextra = [
-                get_string('files'),
-                $file->get_filepath(),
-            ];
-            $path = $this->get_path(array_merge($subcontext, $subcontextextra), $file->get_filename());
+            $pathitems = array_merge(
+                $subcontext,
+                [$this->get_files_target_path($file->get_component(), $file->get_filearea(), $file->get_itemid())],
+                [$file->get_filepath()]
+            );
+            $path = $this->get_path($pathitems, $file->get_filename());
             check_dir_exists(dirname($path), true, true);
             $this->files[$path] = $file;
         }
@@ -285,6 +286,26 @@ class moodle_content_writer implements content_writer {
         return preg_replace('@' . DIRECTORY_SEPARATOR . '+@', DIRECTORY_SEPARATOR, $filepath);
     }
 
+    /**
+     * Get a path within a subcontext where exported files should be written to.
+     *
+     * @param string $component The name of the component that the files belong to.
+     * @param string $filearea The filearea within that component.
+     * @param string $itemid Which item those files belong to.
+     * @return string The path
+     */
+    protected function get_files_target_path($component, $filearea, $itemid) : string {
+
+        // We do not need to include the component because we organise things by context.
+        $parts = ['_files', $filearea];
+
+        if (!empty($itemid)) {
+            $parts[] = $itemid;
+        }
+
+        return implode(DIRECTORY_SEPARATOR, $parts);
+    }
+
     /**
      * Write the data to the specified path.
      *
diff --git a/privacy/classes/tests/request/content_writer.php b/privacy/classes/tests/request/content_writer.php
index 78c1c62624a..c7e2f02116a 100644
--- a/privacy/classes/tests/request/content_writer.php
+++ b/privacy/classes/tests/request/content_writer.php
@@ -385,6 +385,10 @@ class content_writer implements \core_privacy\local\request\content_writer {
     /**
      * Prepare a text area by processing pluginfile URLs within it.
      *
+     * Note that this method does not implement the pluginfile URL rewriting. Such a job tightly depends on how the
+     * actual writer exports files so it can be reliably tested only in real writers such as
+     * {@link core_privacy\local\request\moodle_content_writer}.
+     *
      * @param   array           $subcontext The location within the current context that this data belongs.
      * @param   string          $component  The name of the component that the files belong to.
      * @param   string          $filearea   The filearea within that component.
@@ -393,7 +397,7 @@ class content_writer implements \core_privacy\local\request\content_writer {
      * @return  string                      The processed string
      */
     public function rewrite_pluginfile_urls(array $subcontext, $component, $filearea, $itemid, $text) : string {
-        return str_replace('@@PLUGINFILE@@/', 'files/', $text);
+        return $text;
     }
 
     /**
diff --git a/privacy/tests/moodle_content_writer_test.php b/privacy/tests/moodle_content_writer_test.php
index e0dcb627cae..f919bfdb2a3 100644
--- a/privacy/tests/moodle_content_writer_test.php
+++ b/privacy/tests/moodle_content_writer_test.php
@@ -340,7 +340,7 @@ class moodle_content_writer_test extends advanced_testcase {
             'component' => 'core_privacy',
             'filearea' => 'tests',
             'itemid' => 0,
-            'path' => '/',
+            'path' => '/sub/',
             'name' => 'b.txt',
             'content' => 'Test file 1',
         ];
@@ -389,7 +389,7 @@ class moodle_content_writer_test extends advanced_testcase {
                 'filename'  => $file->name,
             ];
 
-            $file->namepath = $file->path . $file->name;
+            $file->namepath = '/' . $file->filearea . '/' . ($file->itemid ?: '') . $file->path . $file->name;
             $file->storedfile = $fs->create_file_from_string($record, $file->content);
         }
 
@@ -401,14 +401,14 @@ class moodle_content_writer_test extends advanced_testcase {
 
         $firstfiles = array_slice($files, 0, 2);
         foreach ($firstfiles as $file) {
-            $contextpath = $this->get_context_path($context, [get_string('files')], $file->namepath);
+            $contextpath = $this->get_context_path($context, ['_files'], $file->namepath);
             $this->assertTrue($fileroot->hasChild($contextpath));
             $this->assertEquals($file->content, $fileroot->getChild($contextpath)->getContent());
         }
 
         $otherfiles = array_slice($files, 2);
         foreach ($otherfiles as $file) {
-            $contextpath = $this->get_context_path($context, [get_string('files')], $file->namepath);
+            $contextpath = $this->get_context_path($context, ['_files'], $file->namepath);
             $this->assertFalse($fileroot->hasChild($contextpath));
         }
     }
@@ -421,16 +421,16 @@ class moodle_content_writer_test extends advanced_testcase {
      * @param   string  $filename File name
      * @param   string  $content Content
      */
-    public function test_export_file($filepath, $filename, $content) {
+    public function test_export_file($filearea, $itemid, $filepath, $filename, $content) {
         $this->resetAfterTest();
         $context = \context_system::instance();
-        $filenamepath = $filepath . $filename;
+        $filenamepath = '/' . $filearea . '/' . ($itemid ?: '') . $filepath . $filename;
 
         $filerecord = array(
             'contextid' => $context->id,
             'component' => 'core_privacy',
-            'filearea'  => 'tests',
-            'itemid'    => 0,
+            'filearea'  => $filearea,
+            'itemid'    => $itemid,
             'filepath'  => $filepath,
             'filename'  => $filename,
         );
@@ -444,7 +444,7 @@ class moodle_content_writer_test extends advanced_testcase {
 
         $fileroot = $this->fetch_exported_content($writer);
 
-        $contextpath = $this->get_context_path($context, [get_string('files')], $filenamepath);
+        $contextpath = $this->get_context_path($context, ['_files'], $filenamepath);
         $this->assertTrue($fileroot->hasChild($contextpath));
         $this->assertEquals($content, $fileroot->getChild($contextpath)->getContent());
     }
@@ -457,36 +457,50 @@ class moodle_content_writer_test extends advanced_testcase {
     public function export_file_provider() {
         return [
             'basic' => [
+                'intro',
+                0,
                 '/',
                 'testfile.txt',
                 'An example file content',
             ],
             'longpath' => [
+                'attachments',
+                '12',
                 '/path/within/a/path/within/a/path/',
                 'testfile.txt',
                 'An example file content',
             ],
             'pathwithspaces' => [
+                'intro',
+                0,
                 '/path with/some spaces/',
                 'testfile.txt',
                 'An example file content',
             ],
             'filewithspaces' => [
+                'submission_attachments',
+                1,
                 '/path with/some spaces/',
                 'test file.txt',
                 'An example file content',
             ],
             'image' => [
+                'intro',
+                0,
                 '/',
                 'logo.png',
                 file_get_contents(__DIR__ . '/fixtures/logo.png'),
             ],
             'UTF8' => [
+                'submission_content',
+                2,
                 '/Žluťoučký/',
                 'koníček.txt',
                 'koníček',
             ],
             'EUC-JP' => [
+                'intro',
+                0,
                 '/言語設定/',
                 '言語設定.txt',
                 '言語設定',
@@ -835,4 +849,51 @@ class moodle_content_writer_test extends advanced_testcase {
             return $rcm->invoke($writer, $subcontext, $name);
         }
     }
+
+    /**
+     * Test correct rewriting of @@PLUGINFILE@@ in the exported contents.
+     *
+     * @dataProvider rewrite_pluginfile_urls_provider
+     * @param string $filearea The filearea within that component.
+     * @param int $itemid Which item those files belong to.
+     * @param string $input Raw text as stored in the database.
+     * @param string $expectedoutput Expected output of URL rewriting.
+     */
+    public function test_rewrite_pluginfile_urls($filearea, $itemid, $input, $expectedoutput) {
+
+        $writer = $this->get_writer_instance();
+        $writer->set_context(\context_system::instance());
+
+        $realoutput = $writer->rewrite_pluginfile_urls([], 'core_test', $filearea, $itemid, $input);
+
+        $this->assertEquals($expectedoutput, $realoutput);
+    }
+
+    /**
+     * Provides testable sample data for {@link self::test_rewrite_pluginfile_urls()}.
+     *
+     * @return array
+     */
+    public function rewrite_pluginfile_urls_provider() {
+        return [
+            'zeroitemid' => [
+                'intro',
+                0,
+                '<p><img src="@@PLUGINFILE@@/hello.gif" /></p>',
+                '<p><img src="_files/intro/hello.gif" /></p>',
+            ],
+            'nonzeroitemid' => [
+                'submission_content',
+                34,
+                '<p><img src="@@PLUGINFILE@@/first.png" alt="First" /></p>',
+                '<p><img src="_files/submission_content/34/first.png" alt="First" /></p>',
+            ],
+            'withfilepath' => [
+                'post_content',
+                9889,
+                '<a href="@@PLUGINFILE@@/embedded/docs/muhehe.exe">Click here!</a>',
+                '<a href="_files/post_content/9889/embedded/docs/muhehe.exe">Click here!</a>',
+            ],
+        ];
+    }
 }