Sent mail is not being received

Some of my emails use my me.com account are not being received by the recipient.
The emails show being SENT in my SENT box.

I have a similar but perhaps unrelated problem. Every now and then, I send an email on my gmail account using Mail. The sent mail appears in my sent box, but never arrives, and does not appear in my webmail sent box (where it usually does, using gmail). Most of the time it works, and it even works most of the time with people it has had a problem with, including mail I send to myself at work at my professional address. Usually arrives...but not always. I don't know how to trust my sent mail box without always going on the webmail to make sure it actually went out. I only have this problem when using the Mail application, but there are no other common characteristics (attachements, ISPs, etc) to say there could be a problem with one of those things. Anyone else have this problem?
Susannah

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