Reverse order of email chain

Question

How do I reverse the order of an email chain, with the oldest mail at the top and the newest reply at the bottom?

Answer 1

Hello Matt Dale

I understand that you want to change the order of messages inside a conversation, with the oldest email at the top and the newest reply at the bottom.

In New Outlook, there is a setting under Settings > Layout that gives you more control over how conversations are displayed.

However, in Classic Outlook for Windows, I’m afraid this is not supported, as also noted by Q&A Assist. When “Show as Conversations” is enabled, Outlook does not allow reversing the order of messages inside a conversation only. If you attempt to change the sort order, it applies to the entire mailbox view, not just individual conversations.

There are a couple of alternative options you can consider:

• Turn off “Show as Conversations”, and then sort emails by date (Oldest on Top or Newest on Top).
• Use Outlook on the web or New Outlook for desktop and test whether their behavior better matches your preferred reading order.

As an alternative, you may consider raising this idea in the Microsoft Feedback portal, where it can be reviewed for future product improvements.

I understand this is likely not the answer you were hoping for, however, this behavior is by design in Classic Outlook and not a configuration issue. 

Thank you for your understanding, and I appreciate your patience with this behavior.

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Answer 2

In classic Outlook for Windows, the order of messages inside a conversation (email chain) is fixed: newest on top. This order cannot be reversed so that the oldest message appears at the top and the newest at the bottom.

What can be changed is whether messages are grouped into conversations at all:

1. Go to any mail folder (for example, Inbox).
2. Select View > Show as Conversations to toggle Conversation view on or off.
3. Choose All mailboxes or This folder.

Within each conversation, Outlook always sorts with the newest message on top and does not provide an option to reverse that internal order.

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References:

• View email messages by conversation in Outlook
• Sort email messages in Outlook