In iMessage on iPad, no picture shows up for my sent texts, but does for received ones

I have a photo set for contacts, including both e-mail addresses used by iMessage on my iPad. If I send a message to myself, the received message has a picture icon, but not the sent one.
Any ideas?

That is the intended behavior. Pictures in the Inbox help you to quickly identify who sent the email, or message. That is unnecessary in the Sent listing as you are the only one who is sending them and, I hope, you know who you are.
(before you go there, it does not practical to add a picture of the person you are sending to, since you might be sending it to multiple recipients.)

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In iMessage on iPad, no picture shows up for my sent texts, but does for received ones

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