Hi Looneytune42,
It sounds like you can't send emails through iCloud on the website to your work email it says it's undeliverable. In that case, we'd test sending another email to see if this only happens when you attempt to send it to your work email address. You could email your own iCloud account and it should show up in the iCloud inbox, if it successfully sends the email.
If you do test sending another email from iCloud to your work email, we'd confirm the contact is reflecting the correct email account before you select it or type it in manually.
On the iCloud website, if you select your name or icon on the top right side, it should take you to the account details. Do you have enough available iCloud storage? Sometimes the email account stops working if there isn't enough space to store the messages.
Hoping to hear back, cheers.