Plugins and WordPress Version Won't Update

I am having an issue with updating my plugins and wordpress version. When I try to go into the dashboard to update my plugins (currently 6 need updated) I get the following error:

The update process is starting. This process may take a while on some hosts, so please be patient.

Enabling Maintenance mode…

Updating Plugin Captcha (1/1)
Downloading update from https://downloads.wordpress.org/plugin/captcha.4.0.8.zip…
Unpacking the update…
An error occurred while updating Captcha: Could not copy file. captcha/images/cptch_difficulty_word.jpg
Disabling Maintenance mode…

All updates have been completed.

I tried manually uploading a plugin through an FTP, it will appear under wp-content/plugins/ but it will not show up in the dashboard under plugins.

I have the same issues when trying to update my wordpress version from 4.0.1 to 4.1

I tried reseting the permissions of the upgrade folder to 777 as well as deleting and recreating the upgrade folder.

This is happening on two different wordpress instances I have that share the same database, although 3 other sites I manage do not have this issue at all.

Any suggestions?