Can’t send pictures from iPhone to iPad using iMessages

I had two pictures on my iPhone that I needed to get onto my iPad.
I typically use iMessages when going between devices. Sometimes I just create a draft message in gmail and add the pictures as an attchment- I shouldn’t need to resort to this though.

I sent each picture in a separate msgs from the phone to the same phone number that is registered for my iCloud account. The pictures never showed up on my iPad. I rebooted the iPad and waited a while, still no pictures in iMessages. Then I signed out of my iCloud on my iPad. When I signed back in I was prompted for the passcode and entered it.

Then “an error occurred trying to save the iCloud account” was displayed”. I clicked OK, then was prompted again to enter the passcode. Now the passcode dialog is stuck on the screen. This happened to me the last time I logged out & into iCloud on the iPad.

Both the phone and iPad have the most recent version of iOS and are logged into the same iCloud account. I’m not sure what to try next.

I’ve never used iMessage.

Toss 'em into Notes.

That might work, but
It’s not just an issue with the pictures though.

I see messages on my iPad that aren’t showing up in my phone and vice versa. Something isn’t syncing correctly.

What about the passcode screen that never goes way???

I don’t have that problem. I don’t know if the two are interrelated but you might want to disable Messages then re-enable, or follow any of the many guides on iCloud/iMessage sync, like this one:

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From your description I would think this has nothing to do with iMessage (though it demonstrates itself that way)
I think this is related to your iCloud account on the iPad having issues with either iCloud authorization or the iCloud keychain. (Is iCloud keychain enabled on the iPad?)

If the dialog stays on screen all the time I would consider doing a nuke&pave on the iPad.
(DFU restore maybe?)

To verify: if you look at iMessage on a Mac (if you have one) does the iMessage show up there?

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I’ve looked at iMessages on my Mac, the pictures are there that were sent from my iPhone. I’ve backed up the iPad to the Mac using iMazing.

iCloud Keychain is enabled on the iPad too.

If I do the “nuke &pave”, when I restore the iPad data with iMazing, won’t that s as Leo put my iPad back into this bad state?

BTW- how do I nuke &pave the iPad?

I think you’re on to something. Under Share Name and Photo on the iPad, it shows off. When I tap that option, a dialogue is displayed. On the “Hi it’s me” screen, it is toggling between my name and the email address that is registered with my Apple ID.

A while ago, I created a Memoji for my Apple ID icon- on my iPhone. The picture that shows up in Contacts of my friends

Here’s the easy option;

and the “if all else fails” option

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I’ve restored to factory settings then restored from a recent backup using iMazing. The iPad is still on the “updating iCloud Settings “ screen for at least 20 minutes. Is this normal?

I have no idea. I’ve never done an iMazing restore, just iCloud restores. But I would give it some time.
What does the iMazing log say?

That part of the restore was “Updating iCloud settings”, had nothing to do with iMazing.

It finally finished, my iPad looks like everything was restored. Including iMessages, in its broken state.

I’ll make an appt with the Genius Bar.

Thanks anyway