Icloud mail will not send to multiple people?

My icloud mail to multiple people wll make the swish when it is sent and then it is gone.  It does not even show up in the sent file.  I have to start the email again.  After 2 or 3 tries it finally send and shows up in my sent file after several minutes.  Anyone else having this problem?
LRanson

Thank you for coming to my rescue! I've checked the email addresses and they're fine... at least they are fine when I look in my contacts. It would appear that when I start writing the address in the 'to' space and it auto-completes then it works. However, if I click on the address book icon in mail then start double clicking on addresses in there, I come up with a problem. I think I might have come up with where the problem is - when the error message (address not valid) shows, it tells me which addresses are not recognised - I clicked on those addresses (in a saved draft) to check them out and when I do, they only show the recipient's name but not their email address - the ones not named as having a problem show the email address. I'm baffled as all the contacts were imported the same way and as when I go into my Contacts, the details of the problematic addresses look exactly the same as the ones without issues... so so strange!

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