I’m one of the devs working on WP Migrate DB Pro and have been looking into this problem. So far I’ve been unable to replicate the issue either pushing or pulling media into a new trellis/bedrock/sage dev install.
If you’re having this problem and you can share a vm or can walk me through a way to reliably replicate the issue, please reply or send me a PM. We’d really like to figure out what’s going on and get this fixed for our next release.
Thanks to @doug’s help I’ve been able to track this issue down. We’ll have a fix in our next release of WP Migrate DB Pro.
In the meantime, if you’re experiencing this issue on version 1.5.2, the workaround is to add the following to your site’s wp-config.php (or probably the config/application.php file in trellis):
// Don't use WP_Filesystem class for filesystem operations in WP Migrate DB Pro
define( 'WPMDB_WP_FILESYSTEM', false );