Apple - Outlook 2016 - show sent messages in conversation list on the left

I have the same problem in Outlook 2011 for Mac; I think this configuration is not possible.

As shown in the following links from the MS documentation, it looks like the option exists for the Windows version, but it is not available in the Mac OS X version. As you alluded to, (your own) sent messages appear in in "reading pane" but do not render in the message list.

One workaround is to automatically BCC yourself on everything. Enable this by Outlook menu -> Preferences... -> Email section -> Composing -> Format and account section -> enable "When sending messages, automatically BCC myself." This will have the effect of putting a copy of messages you send into your Inbox, so they will render in the conversation view/pane. I'm not sure if this will result in duplicate messages rendering in the "reading pane" for conversations. I'm personally not willing to do this, but it should/does work.

Until or unless...

I'm missing something, or
I learn some fancy keyboard shortcut or other UI trick, or
Give up my convictions and BCC myself on everything (which does render properly),

this interface (and its inconsistency) is unusable. Back to Apple Mail for me.

I found the answer! It involves using the applescript editor to get it to work.

http://joe.blog.freemansoft.com/2016/02/received-and-sent-messages-in-single.html

Run Outlook

Highlight the Mailbox we are going to include, Inbox or Sent. We want to get this mailbox's folder id.

Start a Mac Spotlight search

Enter ~applesoft~ AppleScript Editor and Enter to bring up the applesoft editor.
Enter the following in the applescript editor and run it
on run {}
tell application "Microsoft Outlook"
get selected folder
end tell
end run
It should return the results of the execution mail folder id 109 of application "Microsoft Outlook" Do the same thing for the other mailbox. My mailbox numbers were 109 (Inbox) and 112 (Sent)
Click on the Search field in the upper right hand corner of the Outlook view.

This will enable the search tab and ribbon

Select the Search tab

Make sure you are still have a normal mailbox selected (not a Smart Folder)

Select "All Mail" in the Ribbon Bar

Press the Advanced search button in the ribbon

Select Raw Query from the drop list.
Enter the following query, replacing 109 and 112 with the mailboxes numbers retrieved above.
com_microsoft_outlook_folderID == 109 || com_microsoft_outlook_folderID == 112
Press Enter. The message list should populate with the combined content of the two folders. Conversations in this combined Index/Sent folder will include both inbound and outbound messages.

Press Save Search in the Search ribbon bar and enter the name of your new Smart Folder.

Another helpful link was a list of all the Raw Query keys:

https://gist.github.com/EmilVarona/78ae2aff409922686ebff4cea785aed4

<?xml version="1.0" encoding="UTF-8"?>
<schema version="1.0" xmlns="http://www.apple.com/metadata" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.apple.com/metadata file:///System/Library/Frameworks/CoreServices.framework/Frameworks/Metadata.framework/Resources/MetadataSchema.xsd">
  <!--  
    Compiled from /Applications/Microsoft\ Outlook.app/Contents/Library/Spotlight/Microsoft\ Outlook\ Spotlight\ Importer.mdimporter/Contents/Resources/schema.xml
    with info from http://xensoft.com/search-mac-outlook-2011-mail-with-raw-queries/
  -->
      <types>
        <type name="com.microsoft.outlook15.contact">
            <allattrs>
                kMDItemTitle
                kMDItemPhoneNumbers
                kMDItemEmailAddresses
                kMDItemInstantMessageAddresses
                kMDItemContentModificationDate
                com_microsoft_outlook_recordID
                com_microsoft_outlook_folderID
                com_microsoft_outlook_accountID
                kMDItemCity
                kMDItemStateOrProvince
                kMDItemCountry
                com_microsoft_outlook_flag
                com_microsoft_outlook_nickname
                com_microsoft_outlook_company
                com_microsoft_outlook_department
                com_microsoft_outlook_jobTitle
                com_microsoft_outlook_homeURL
                com_microsoft_outlook_workURL
                com_microsoft_outlook_bloodType
                com_microsoft_outlook_spouse
                com_microsoft_outlook_customFld1
                com_microsoft_outlook_customFld2
                com_microsoft_outlook_customFld3
                com_microsoft_outlook_customFld4
                com_microsoft_outlook_customFld5
                com_microsoft_outlook_customFld6
                com_microsoft_outlook_customFld7
                com_microsoft_outlook_customFld8
                com_microsoft_outlook_homeStreet
                com_microsoft_outlook_homeCity
                com_microsoft_outlook_homeState
                com_microsoft_outlook_homeZip
                com_microsoft_outlook_homeCountry
                com_microsoft_outlook_firstName
                com_microsoft_outlook_lastName
                com_microsoft_outlook_suffix
                com_microsoft_outlook_title
                com_microsoft_outlook_notes
                com_microsoft_outlook_workStreet
                com_microsoft_outlook_workCity
                com_microsoft_outlook_workState
                com_microsoft_outlook_workZip
                com_microsoft_outlook_workCountry
                com_microsoft_outlook_otherStreet
                com_microsoft_outlook_otherCity
                com_microsoft_outlook_otherState
                com_microsoft_outlook_otherZip
                com_microsoft_outlook_otherCountry
                com_microsoft_outlook_interests
                com_microsoft_outlook_japanese
                com_microsoft_outlook_birthday
                com_microsoft_outlook_anniversary
                com_microsoft_outlook_customDate1
                com_microsoft_outlook_customDate2
                com_microsoft_outlook_children
                com_microsoft_outlook_furigana_full_name
                com_microsoft_outlook_firstNameFurigana
                com_microsoft_outlook_lastNameFurigana
                com_microsoft_outlook_companyFurigana
                com_microsoft_outlook_spouseFurigana
                com_microsoft_outlook_childrenFurigana
                com_microsoft_outlook_interests
                com_microsoft_outlook_projects
                com_microsoft_outlook_categories
                com_microsoft_outlook_primaryCategory
                com_microsoft_outlook_flagged
                com_microsoft_outlook_isgroup
                com_microsoft_outlook_hasStartDate
                com_microsoft_outlook_startDate
                com_microsoft_outlook_hasDueDate
                kMDItemDueDate
                com_microsoft_outlook_has_reminder
                com_microsoft_outlook_completed
                com_microsoft_outlook_completedDate
            </allattrs>
            <displayattrs>kMDItemTitle
                kMDItemPhoneNumbers
                kMDItemEmailAddresses
                kMDItemInstantMessageAddresses
                kMDItemContentModificationDate
            </displayattrs>
        </type>
        <type name="com.microsoft.outlook15.event">
            <allattrs>com_microsoft_outlook_has_text_content
                kMDItemTextContent
                kMDItemTitle
                com_microsoft_outlook_recordID
                com_microsoft_outlook_folderID
                com_microsoft_outlook_accountID
                kMDItemCoverage
                kMDItemDueDate
                com_microsoft_outlook_hasStartDate
                com_microsoft_outlook_hasDueDate
                com_microsoft_outlook_startDate
                com_microsoft_outlook_endDate
                kMDItemWhereFroms
                kMDItemComment
                com_microsoft_outlook_timeZone
                com_microsoft_outlook_recurrence
                com_microsoft_outlook_recurring
                com_microsoft_outlook_allDay
                com_microsoft_outlook_has_reminder
                com_microsoft_outlook_freeBusy
                com_microsoft_outlook_free_busy_value
                com_microsoft_outlook_parentRecordID
                kMDItemContactKeywords
                kMDItemKeywords
                kMDItemProjects
                com_microsoft_outlook_projects
                com_microsoft_outlook_categories
                com_microsoft_outlook_primaryCategory
                com_microsoft_outlook_attendees
                com_microsoft_outlook_attendee_emails
            </allattrs>
            <displayattrs>kMDItemTitle
                kMDItemCoverage
                kMDItemDueDate
                kMDItemWhereFroms
           </displayattrs>
        </type>
        <type name="com.microsoft.outlook15.message">
            <allattrs>kMDItemTitle
                com_microsoft_outlook_recordID
                kMDItemContentCreationDate
                com_microsoft_outlook_messageSent
                com_microsoft_outlook_messageReceived
                com_microsoft_outlook_priority
                com_microsoft_outlook_flag
                com_microsoft_outlook_unread
                kMDItemContentModificationDate
                kMDItemCoverage
                kMDItemKeywords
                kMDItemProjects
                com_microsoft_outlook_has_text_content
                kMDItemTextContent
                kMDItemAuthors
                kMDItemRecipients
                com_microsoft_outlook_folderID
                com_microsoft_outlook_junkLikelihood
                com_microsoft_outlook_size
                com_microsoft_outlook_newsAccountID
                com_microsoft_outlook_accountID
                com_microsoft_outlook_repliedTo
                com_microsoft_outlook_forwarded
                com_microsoft_outlook_redirected
                com_microsoft_outlook_toRecipients
                com_microsoft_outlook_toEmailAddresses
                com_microsoft_outlook_ccRecipients
                com_microsoft_outlook_ccEmailAddresses
                com_microsoft_outlook_bccRecipients
                com_microsoft_outlook_bccEmailAddresses
                com_microsoft_outlook_attachments
                com_microsoft_outlook_has_attachments
                com_microsoft_outlook_has_mentioned_me
                com_microsoft_outlook_projects
                com_microsoft_outlook_categories
                com_microsoft_outlook_primaryCategory
                com_microsoft_outlook_flagged
                com_microsoft_outlook_author_email_addresses            
                com_microsoft_outlook_recpient_email_addresses
                com_microsoft_outlook_isFromMailingList
                com_microsoft_outlook_hasStartDate
                com_microsoft_outlook_startDate
                com_microsoft_outlook_hasDueDate
                kMDItemDueDate
                com_microsoft_outlook_has_reminder
                com_microsoft_outlook_completed
                com_microsoft_outlook_completedDate
            </allattrs>
            <displayattrs>kMDItemContentCreationDate
                kMDItemAuthors
                kMDItemRecipients
                kMDItemCoverage
                kMDItemContentModificationDate
            </displayattrs>
        </type>
        <type name="com.microsoft.outlook15.note">
            <allattrs>kMDItemTitle
                com_microsoft_outlook_recordID
                kMDItemContentCreationDate
                kMDItemContentModificationDate
                com_microsoft_outlook_has_text_content
                kMDItemTextContent
                kMDItemKeywords
                kMDItemProjects
                com_microsoft_outlook_folderID
                com_microsoft_outlook_accountID
                com_microsoft_outlook_projects
                com_microsoft_outlook_categories
                com_microsoft_outlook_primaryCategory
            </allattrs>
            <displayattrs>kMDItemTitle
                kMDItemContentCreationDate
                kMDItemContentModificationDate
            </displayattrs>
        </type>
        <type name="com.microsoft.outlook15.task">
            <allattrs>com_microsoft_outlook_has_text_content
                kMDItemTextContent
                kMDItemTitle
                com_microsoft_outlook_recordID
                kMDItemContentModificationDate
                kMDItemComment
                com_microsoft_outlook_recurring
                com_microsoft_outlook_recurrence
                com_microsoft_outlook_recurrence_type
                com_microsoft_outlook_priority
                com_microsoft_outlook_folderID
                com_microsoft_outlook_accountID
                kMDItemProjects
                com_microsoft_outlook_projects
                com_microsoft_outlook_categories
                com_microsoft_outlook_primaryCategory
                com_microsoft_outlook_hasStartDate
                com_microsoft_outlook_startDate
                com_microsoft_outlook_hasDueDate
                kMDItemDueDate
                com_microsoft_outlook_has_reminder
                com_microsoft_outlook_completed
                com_microsoft_outlook_completedDate
            </allattrs>
            <displayattrs>kMDItemTitle
                kMDItemDueDate
            </displayattrs>
        </type>
    </types>
</schema>

Hope that helps.

Another related link: http://blog.stevex.net/2011/03/outlook-2011-smart-folder-with-raw-query/ Info on mdl query syntax: https://developer.apple.com/library/archive/documentation/Carbon/Conceptual/SpotlightQuery/Concepts/QueryFormat.html

Value examples that you can make a raw query against.

com_microsoft_outlook_accountID                = 1
com_microsoft_outlook_author_email_addresses   = (
    "*** Email address is removed for privacy ***"
)
com_microsoft_outlook_categories               = (
    98
)
com_microsoft_outlook_completed                = 0
com_microsoft_outlook_flagged                  = 0
com_microsoft_outlook_folderID                 = 108
com_microsoft_outlook_forwarded                = 0
com_microsoft_outlook_has_attachments          = 0
com_microsoft_outlook_has_mentioned_me         = 0
com_microsoft_outlook_has_reminder             = 1
com_microsoft_outlook_has_text_content         = 1
com_microsoft_outlook_hasDueDate               = 0
com_microsoft_outlook_hasStartDate             = 0
com_microsoft_outlook_messageReceived          = 2016-09-01 20:46:56 +0000
com_microsoft_outlook_messageSent              = 2016-09-01 20:46:54 +0000
com_microsoft_outlook_primaryCategory          = 98
com_microsoft_outlook_priority                 = 0
com_microsoft_outlook_recordID                 = 646385
com_microsoft_outlook_recpient_email_addresses = (
    "*** Email address is removed for privacy ***"
)
com_microsoft_outlook_redirected               = 0
com_microsoft_outlook_repliedTo                = 0
com_microsoft_outlook_size                     = 4
com_microsoft_outlook_toEmailAddresses         = (
    "*** Email address is removed for privacy ***"
)
com_microsoft_outlook_toRecipients             = (
    "GUPTA, Sunil"
)
com_microsoft_outlook_unread                   = 1
kMDItemAlternateNames                          = (
    "/Users/i804008/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles/Main Profile/Data/Messages/143/8F74F504-DF2B-40C7-8AFE-7AF73D95486D.olk15Message"
)
kMDItemAuthors                               = (
    "Wu, Will"
)
kMDItemContentCreationDate                     = 2016-09-01 20:46:56 +0000
kMDItemContentModificationDate                 = 2016-09-01 20:47:02 +0000
kMDItemContentType                             = "com.microsoft.outlook15.message"
kMDItemContentTypeTree                         = (
    "com.microsoft.outlook15.message",
    "public.email-message",
    "public.message",
    "public.data",
    "public.item"
)
kMDItemDateAdded                               = 2016-09-01 20:47:01 +0000
kMDItemDisplayName                             = "aabbccdd"
kMDItemFSContentChangeDate                     = 2016-09-01 20:47:02 +0000
kMDItemFSCreationDate                          = 2016-09-01 20:47:01 +0000
kMDItemFSCreatorCode                           = ""
kMDItemFSFinderFlags                           = 0
kMDItemFSHasCustomIcon                         = (null)
kMDItemFSInvisible                             = 0
kMDItemFSIsExtensionHidden                     = 0
kMDItemFSIsStationery                          = (null)
kMDItemFSLabel                               = 0
kMDItemFSName                               = "8F74F504-DF2B-40C7-8AFE-7AF73D95486D.olk15Message"
kMDItemFSNodeCount                             = (null)
kMDItemFSOwnerGroupID                          = 1694527156
kMDItemFSOwnerUserID                           = 718023034
kMDItemFSSize                               = 4583
kMDItemFSTypeCode                              = ""
kMDItemKind                               = "olk15_message"
kMDItemLastUsedDate                            = 2016-09-01 20:46:56 +0000
kMDItemLogicalSize                             = 4583
kMDItemPhysicalSize                            = 8192
kMDItemRecipients                              = (
    "GUPTA, Sunil"
)
kMDItemTitle                               = "aabbccdd"
kMDItemUseCount                               = 1
kMDItemUsedDates                               = (
    "2016-09-01 04:00:00 +0000"
kMDItemOwnerUserID                    = 718023034
com_microsoft_outlook_accountID        = 1
com_microsoft_outlook_allDay           = 0

Apple - Outlook 2016 - show sent messages in conversation list on the left

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