View of file entities, sorted by upload date, reorders when updating a file
A quick check with drupal_get_schema() confirms that file entities have only one associated time column called timestamp; there is no separate "upload" and "modified" date. So that timestamp, presumably, gets updated every time the file entity gets saved.

This makes sense from a certain standpoint because editing a file entity could involve updating the file itself.

I decided to take a crack at a custom module that would add a new "upload date" column to the file entity table. This may be completely wrong, and I haven't tested it, so do NOT try to use it on a production website until you're sure it works, but it might just give you what you're looking for.

In mymodule.install:

function mymodule_install() {
  // Add a column to the file table for your new creation date field.
  db_add_field('file_managed', 'upload_date', array(
    'type' =&gt; 'int',
    'unsigned' =&gt; TRUE,
    'not null' =&gt; TRUE,
    'default' =&gt; 0
  ));
  // Load all existing files and set their upload date to be equal to their current timestamp.
  $files = entity_load($file);
  foreach($files as $file) {
    $file-&gt;upload_date = $file-&gt;timestamp;
    file_save($file);
  }
}
// Drop the new field if the module is uninstalled.
function mymodule_uninstall() {
  db_drop_field('file_managed', 'upload_date');
}


In mymodule.module:

// Set the upload time field to the current time when the file is first saved
function mymodule_file_presave($file) {
  if(!isset($file-&gt;upload_date) || $file-&gt;upload_date == 0) {
    $file-&gt;created_date = time();
  }
}
// @TODO make the upload date field editable.


In mymodule.views.inc:

// Add a field handler for your new field.
function mymodule_views_data_alter(&amp;$data) {
  $data['file']['upload_date'] = array(
    'title' =&gt; t("Upload date"),
    'help'  =&gt; t("The date the file was first uploaded."),
    'field' =&gt; array(
      'handler' =&gt; 'views_handler_field_date',
    ),
  );
}


Assuming that I didn't screw up, once the module is installed you'll need to add the upload date field to your view and use it for sorting.