Mail does not (always) display sent messages w/attachments

Hello,
A frustration: my Mail 8.2 (using iCloud and OS X 10.2.2) often does not display particular Sent messages -- this most often occurs when I have multiple attachments and have spent quite some time, often approaching half an hour, composing the message -- but sometimes it occurs when only a single attachment and a quick, 10 second, composition period. Recipients report receiving the emails and the attachments. The vast majority of Sent messages are properly displayed.
I have searched for the missing Sents by recipient, subject line and even text and .... they do not appear in any mailbox.
Wi-Fi connections are strong and not problematic. The issue is not particular to any one recipient. All software updates are current.
While it has been some time since I Repaired Permissions I am not detecting any other problems.
The frustration is "OMG where did that half-hour of work GO?" followed by a usually unnecessary follow-up email or call to the recipient.
Any suggestions would be appreciated; thanks.

Hi Linc,
As per my original question.
Using iCloud, which is as you know IMAP. I noticed it does not occurr with pop mail servers. Thank you for looking into this.

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