I have been having exactly the same problem lately. I send a test email to check the layout etc and sometimes it never arrives! (not going into Junk) Other times it works fine. If I choose a different email address for the test email it works! All a bit unreliable. Any ideas what is wrong?
I have EXACTLY the same issue with test emails. I find if I close down the Constant Contact web page and re-open it I can usually send ONE test email then it stops working again.
Welcome back to the Community! Have you tried clearing the cache and history in your browser yet? From what your describing it sounds like that might be the issue! If your browser is too clogged up with data it might not be sending the email like its saying it is. So I would clear the cache, close the browser our completely, and then reopen and try to send multiple tests. Please let us know if this helps.