Issues sending iCloud mail via Mac Mail client

I'm running OS X Yosemite and use the Mac Mail client to handle mail for my iCloud (mac.com), wish.edu, Gmail, and Outlook accounts.  All work fine and always have... until a few weeks ago.  I came to figure out that while sending email through my iCloud account will show up as a sent email in the sent folder (on my MacBook Pro as well as the web interface and IOS devices) the messages do not get received on the other end.  No error messages.  No returns.  Everything looks normal on my end but the emails never get delivered.
I logged out of iCloud and logged back in.  I checks the outgoing server info and passwords. I restarted (a lot).  When I run tests, emails sent from the Mac Mail client on my laptop don't get there.  They do get received when sent via the iCloud web interface as well as from my iPhone and iPad.  I even downloaded PostBox and set it up with the exact same settings as Mac Mail, and it sends the iCloud mail just fine.
This is driving me nuts.  I love Mac Mail, and have used it for years.  I don;t want to have to abandon it for this.  Help?

Hi All,
    I have a requirement where i have to send the Pdf format of the billing document as a mail to the customer. And my client wants to send the mail via outlook so that they can modify the body content for each mail. Right now i have achieved the functionality of sending the mail with Pdf attachment form SAP.
Can anyone please help me by providing some information about how to send mail from SAP via Outlook.
Thanks!
Praveenkumar T.

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