ishitaka

<p>Associate images and posts in the media library at once (set “Uploaded to”).</p>
<h4>Supported media files</h4>
<ul>
<li>Images in post content</li>
<li>Featured images</li>
<li>WooCommerce products and product gallery images</li>
<li>Image Field in Advanced Custom Fields plugin</li>
<li>Image Field in Smart Custom Fields plugin</li>
</ul>


Associate Attachment

Associate the media library image with the post.

Turker YILDIRIM

<p><strong>Be careful when using this plugin.</strong></p>
<p>Sometimes you may need to update files, like product or property photos, without deleting old one before uploading new one. In such cases you can use this plugin to replace old files with new ones.</p>
<p>OverWrite It makes a filename search in <code>wp-content\uploads</code> folder recursively and replaces first matching file with the uploading one.</p>
<p>Keep in mind there is no excluded files, folders or file types so <strong>double check everything before uploading anything</strong> while the plugin is active.</p>
<h3>Languages</h3>
<p>Please consider helping translations at the <a href="https://translate.wordpress.org/projects/wp-plugins/overwrite-it" rel="nofollow ugc">GlotPress project</a>.</p>


OverWrite It

I have been searching for similar plugin, some of them didn't work for me but this one does. Thanks

It works

When you upload files, OverWrite It jumps into the scene to replace old file with uploading one.

Associate Attachment vs OverWrite It