try to overwrite your old plugin files with new plugin files via FTP. You don’t have to deactivate UserPro before doing this.

All of your pages & features will be kept alive.

It won’t OVERRIDE YOUR SETTINGS, but if you modified css file, or templates in core plugin they will be replaced if you didn’t back up.

Solution?

Use the templating way to edit your css/skins/templates. example:

Create /userpro/ folder at your theme folder

now to edit login.php template for example, keep the customized version in login.php in your theme/userpro/ folder rather than /plugins/userpro/templates/ folder got it?

For skins, similar. do in your theme folder userpro/skins/default/style.css (with modified styles, css)

This way you AVOID editing css/templates in CORE plugin and keep updates without an issue.

Central Geek has another solution/approach:

If you install and activate the following plugin “Easy Theme and Plugin Upgrades” (It’s available on WordPress.org), you will be able to upload and update any installed plugin or theme. I have used it for a couple years and it has never failed me yet. I hate having to ftp to update. And this plugin resolves that for me. Just make sure when you go to the “Add New” and choose “Upload” if you have a plugin installed, choose “Yes” in the dropdown before you click on the update button.

Best regards,
keyhanjun

Thanks for your feedback on your initially posted thread which people can find here:

http://userproplugin.com/userpro/forums/topic/ver-1-0-49-upgrade-help-wp-keeps-giving-me-a-failed-error-upon-install/

Best regards,
keyhanjun