some emails don't go into sent folder

Back up all data. Rebuild the mailbox.

Please sign out of iCloud in its preference pane. No data will be removed from the servers, and you can retrieve it by signing back in. That said, you should always have a current archiveof the data for safety's sake, even if you don't sign out.

Also sign out of iMessage and sign back in.

If you use iCloud Keychain, when you sign back in to iCloud follow one of the procedures described in this support article to set it up on an additional device.

Look at the bottom of your Mailbox list for email account Mailboxes. See if there is a Sent or Sent Items mailbox within the amount you are sending from.

If there is, select it and select Sent from the Mailbox>Use this Mailbox for> menu item.

That should merge the account sent mailbox with the unified Sent mailbox.

Scott Raymond wrote:

Thanks, but that isn't it. I already have all my devices set up to be using the same sent folder on the iCloud server. And it just started happening and only seems to happen when I email this one person and include an attachment. Otherwise all of my sent mail is going into that sent folder.

Are they all the same iCloud account? Otherwise, how did you do that?

Can you find the sent message if you search for it? If so, where does it say it is located?

I've tried everything to get that to sync and the only thing that works is creating a new iCloud account but if I do that I lose my email address.

Have you tried creating a new user account on your Mac, set everything up iCloud-wise in that account, and test? It sounds to me like it may be something in your user account on the Mac, not necessarily iCloud. Maybe the indexes aren't getting updated correctly.

Are you missing any sent items from your other devices? i.e. if you send from your iPhone, does it show up in Sent on all other devices (except, perhaps Mac Mail)?

As to the missing text messages, Apple has set up two-factor authentication (app-specific passwords) for Messages. It wasn't that obvious, but until I logged in with that app-specific password, I wasn't getting messages in Messages.

Launch the Console application in any of the following ways:

☞ Enter the first few letters of its name into a Spotlight search. Select it in the results (it should be at the top.)

☞ In the Finder, select Go ▹ Utilities from the menu bar, or press the key combination shift-command-U. The application is in the folder that opens.

☞ Open LaunchPad and start typing the name.

The title of the Console window should be All Messages. If it isn't, select

SYSTEM LOG QUERIES ▹ All Messages

from the log list on the left. If you don't see that list, select

View ▹ Show Log List

from the menu bar at the top of the screen.

Click the Clear Display icon in the toolbar. Then take an action that isn't working the way you expect. Select any lines that appear in the Console window. Copy them to the Clipboard by pressing the key combination command-C. Paste into a reply to this message by pressing command-V.

The log contains a vast amount of information, almost all of which is irrelevant to solving any particular problem. When posting a log extract, be selective. A few dozen lines are almost always more than enough.

Please don't indiscriminately dump thousands of lines from the log into this discussion.

Please don't post screenshots of log messages—post the text.

Some private information, such as your name or email address, may appear in the log. Anonymize before posting.

When you post the log extract, you might see an error message on the web page: "You have included content in your post that is not permitted," or "The message contains invalid characters." That's a bug in the forum software. Please post the text on Pastebin, then post a link here to the page you created.