This appears to date back to 2013, but the problem persists.
If I check the box in general settings to allow attachments to the contact form, I get an error message upon sending a message to admin via contact page. Also, when filling out the contact form there is not even an option to attach file, and it still gives the error message "The file you tried to upload does not have a valid extension". If I go back and uncheck the option to allow attachments then the message will be sent without error message..