MacBook Mail app not showing sent replies above original messages in inbox

MacBook Mail: Sent replies no longer appearing with original messages in Inbox

This sounds like a possible issue with Apple Mail's Conversation View settings or the way your Sent mailbox is configured. 

Since the problem occurs after clicking Send, I would try the following steps on your MacBook Pro (M1, 2020).

1. Check Conversation View

• Open the Mail app.

• Select View >> Organize by Conversation.

• Make sure it is checked.

• If already checked, turn it off and back on.

• Open an original email and look for a disclosure arrow or conversation count to see whether your reply is included in the thread.

Apple's instructions: View email conversations in Mail on Mac.

2. Check the message display order

This is particularly important because you want your sent reply to appear above the original email.

• Go to Mail >> Settings >> Viewing.

• Find Show most recent message at the top.

• Make sure it is selected.

This setting controls the order in which messages appear within a conversation.

Apple's instructions: Read and respond to emails in Mail on Mac.

3. Expand all conversations

• Open Mail.

• Select View >> Expand All Conversations.

• This ensures that all messages within a conversation are displayed rather than hidden behind a message count.

This may restore the appearance you were accustomed to, even though the sent reply is stored in Sent rather than Inbox. 

4. Verify your Sent mailbox settings

• Go to Mail >> Settings >> Accounts.

• Select the affected email account.

• Click Mailbox Behaviours.

• Check that the Sent Mailbox is assigned to the correct Sent folder on your email provider's server.

Avoid changing the setting unless it is incorrectly assigned.

Apple's instructions: Change Mailbox Behaviors settings in Mail on Mac.

5. Rebuild the Inbox if messages still appear missing

If the above steps don't help:

• Select your Inbox in the Mail sidebar.

• Choose Mailbox >> Rebuild.

• Allow Mail time to synchronize and reload the messages.

Apple's instructions: Rebuild mailboxes in Mail on Mac.

One important clarification

Apple Mail normally stores sent replies in the Sent mailbox, not the Inbox.

However, Conversation View is designed to group the original incoming message and your sent reply together, allowing you to see the entire exchange from the Inbox.

Your desired result should therefore be achievable through the conversation display settings, without manually moving sent messages into your Inbox.

My recommendation: Start with Steps 1, 2 and 3 before attempting to rebuild anything.

If the problem continues, check whether it happens with all email accounts or just one (iCloud, Gmail, Yahoo, etc.). That will help narrow down whether this is an Apple Mail issue or an email-provider synchronization issue.

Also check if there are any updates to macOS Golden Gate. System. Setting >> General >> Software Update

The latest version of macOS is 27.2. Learn how to update the software on your Mac and how to allow important background updates.

MacBook Mail app not showing sent replies above original messages in inbox

In Apple Mail, Organize by Conversation (also referred to as View in Conversation) groups related emails so that an entire exchange can be viewed in one place, rather than opening each message individually.

If your Mail application displays Golden Gate 27.0 (Mail version 16), these appear to be separate software or version identifiers and do not, in themselves, determine how conversation threading works.

1. How Organize by Conversation works

To view an email exchange as a conversation:

1. Open Apple Mail.
2. Select the mailbox you want to view, such as Inbox or Sent.
3. Select View >> Organize by Conversation.
4. Locate an email that is part of an existing exchange.
5. If the conversation is collapsed, click the message count at the top of the conversation to reveal the related emails.

To display all messages automatically, select View >> Expand All Conversations.

Apple's official instructions are available here:

Apple Support – Read and respond to emails in Mail on Mac

2. What should you expect to see?

Consider the following example:

Subject: Project Meeting

• Monday – John sends the original email.
• Tuesday – You reply to John.
• Wednesday – John responds to your reply.
• Thursday – You send your latest response.

Ideally, all four messages should be accessible within the same conversation, including both received emails and your sent replies.

3. Why might some messages be missing?

Conversation view does not necessarily guarantee that every related email will appear. Missing messages may be caused by:

• Messages being stored in different mailboxes.

• Your sent replies not appearing in the displayed conversation.

• Changes to the original subject line.

• Missing or inconsistent email threading information.

• Messages having been deleted or moved.

Apple Mail uses message relationships and subject information to identify and group related emails.

4. An important distinction: Conversation settings are mailbox-specific

Organize by Conversation is a viewing preference, not a rule that permanently reorganizes your emails.

Importantly, macOS Mail can maintain this preference independently for each mailbox. Enabling it in your Inbox does not necessarily enable it in Sent, Archive or other mailboxes.

For example:

Mailbox

Organize by Conversation

Inbox ON

Sent OFF

Archive ON

Work OFF

Personal ON

This means you can choose whether to display emails as conversations independently in each mailbox.

If you want a consistent conversation view throughout Mail, you should check the setting in each mailbox you regularly use.

Thank you very much--looks to be in the right place as it "appears" to be related to "show related messages." However, it does not seem to keep the selection when I click on it. Will work when I click on it, but then it appears to sometimes revert to Hide Related Messages. But I think we're closer,... I found a setting in the Settings for Mail (as opposed to the links at the top) which said under "Viewing" - "include related messages" which was not checked so I'll see if this is resolved within the next few days. Again thank you for getting me on the right path!