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If, in my inbox, I click a conversation in the messages pane, even if I have since sent a reply, Outlook 2010 will display the most recently received email in the reading pane. I want it to display the most recently sent or received email in the conversation.

The Outlook Web App shows the entire conversation in the reading pane, with the most recent email active (unfolded), even if it was sent. Even this would be an acceptable alternative (if not preferable).

Note that Outlook 2010 is already in conversation view and does show the sent messages when the conversation is expanded.

Edit: I was able to replicate this somewhat by making a search folder (see below). It would still be nice to get it to work on the inbox.

Edit 2: Partial Solution using a Search Folder:

I was able to make a search folder which included all mail not in Deleted Items, grouped by conversation and sorted by date. In this folder, when I click on a conversation, the most recent email, sent or received, displays in the reading pane. I also favorited the folder for more prominent display, and used NBO's method for making Outlook start in it. This is the exact (nearly, see caveat below) functionality that I want, only in the Inbox.

Caveat

Moving conversations functions differently in search folders than in the Inbox. In the Inbox, moving the conversation to another folder only moves the received* emails. In search folders, all matched* emails (including sent emails) are moved.

*- I haven't thoroughly tested the conditions for when the emails are moved, so more or less of them may be moved than indicated above.

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It took me forever to figure this out. In Outlook 2013 (at least), when you create the Search Folder, the Show as Conversations checkbox in the View ribbon is grayed out. Instead, you have to go to View Settings (same ribbon), then Group By..., uncheck Automatically group according to arrangement, and then under Group items by, choose Conversation. Now the Show as Conversations checkbox is checked. –  Travesty3 Feb 7 at 17:20

2 Answers 2

It's a feature, not a bug.

Outlook shows the messages in the current folder, and if you check the option to "Show Messages from Other Folders", it will also show them in the conversation thread, but will only select by default the last from this folder.

This may be helpful: Under the View tab → Conversation Settings, set all options to "Always expand", and to indent. At least it's visible that there is a newer message you sent.

The other option as you commented is to create a Search folder to include all inbox and sent items and set it as the starting folder for outlook going to "file" - "Options" - "Advanced" and modifying Outlook start and Exit - see screenshots: enter image description here Favorites

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I have seen the "Always Expand" option, and this is nice on small conversations, but is incredibly annoying on large ones. I understand the reasoning why it is only showing me the most recent message in my current folder, but the implementation of the conversation feature is inconsistent between Outlook and OWA. –  user1936123 Mar 13 '13 at 22:15
    
I do like the sound of your rules based solution. Would you mind elaborating on it a bit? Note that if it involves moving both sent and received messages into the same folder, that is definitely not ideal. I'll expand the description of my search folder solution above. –  user1936123 Mar 13 '13 at 22:15
    
With your clarification it is now easy - just make the search folder the starting folder - I'll add images in post above –  NBO Mar 14 '13 at 10:18
    
That's great. I upvoted your answer and updated the body of the question to reflect this. As this is just a workaround (though a very effective one), I'm going to leave the question open for now. If no one provides a proper solution before the last day of the bounty, I'll award it to you. –  user1936123 Mar 14 '13 at 17:43
    
I spoke too soon. There is a significant drawback to this method: if you move a conversation out of the search folder into another folder, even the sent emails are moved. I'll update the question with the caveat. –  user1936123 Mar 14 '13 at 22:56

I have this working in Outlook 2010 and here is what I did. How it looks for me

  1. Under View-> conversations select "show as conversations
  2. Under Conversations-> conversations settings check "show messages from other folders
  3. Under Arrangement-> view settings->sort-> select: received-> descending View Settings

This will show all conversation in a string, deleted, sent and received.

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#1 and #2 were already done. After changing #3, clicking an email in my inbox still shows my most recently received message, even if a more recently sent message exists. –  user1936123 Mar 12 '13 at 18:11
    
Added screen shots –  Ryan E Mar 12 '13 at 21:45
    
I see what you are getting at there. As mentioned, I can already see the sent items when the conversation is expanded. Regardless of the sort order, clicking the conversation displays the most recently received email in the conversation in the reading pane. I have updated the question in an attempt to clarify for what I am looking. –  user1936123 Mar 12 '13 at 22:17

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