Automation & sent message Issue - IF Prospect Effectively Opened Message

I am experiencing what I believe to be two issues.

The first is with automations I am attempting to set up. I want to use the "IF Prospect Effectively Opened Message" logic and selected a message I sent outside of the automation (I sent manually), and this is not giving me the outcome I am looking for. Does an email have to be sent within the automation in order for this logic to work? My desired outcome is that if they opened email 1, they will receive email 2. If they did not open it, they will receive a resend of email 1.

The second is with sent messages. I noticed that when I check my Outbound >> Sent folder there is only one message sent (I sent the email on Tuesday to five separate lists from one sender within one email message), but when I went to set up segments for the lists I used for that send (I wanted people who opened to the message to be added to a different segment), it showed that I had sent that message EIGHT times. This message is not included in any automation I currently have running. When I selected only one of these lists, I did not get accurate results for my segment. When I selected all of them, the correct amount of people who opened my message did populate the segment. 

I am so confused by these two things and my automations are not running as desired. Any guidance is appreciated, thank you!