Welcome to the community @lily
For a list-triggered flow, a contact will enter that flow only once: when they initially subscribe to the list.
In your screenshot, the contact has subscribed twice to your ‘Newsletter’ list. Once on 5th July 23 and again on 30th January 24. Their most recent subscription on the 30th won’t trigger the Newsletter flow so they won’t receive any emails from it.
However, they should have received a Newsletter flow email on the 5th July 23 assuming the flow on that date was configured correctly. As they didn’t, I suggest you check the profile’s ‘view messages’ to see if there’s a reason for them being skipped. That could include smart send enabled invalid email address, or failed a flow filter.
Hope that helps
Andy