So far Outlook 2011 is the only thing that handles this properly. OWA and Outlook 2016 have the same problem. Plenty more examples on office tech center: https://social.technet.microsoft.com/Forums/office/en-US/a8f8e96c-fdee-45d6-bdfa-b25f8b919e3e/outlook-for-mac-2016-conversations-grouping?forum=outlook
This used to work, but stopped a version or two ago. Now all emails with the same subject no longer are grouped into conversations, and it has really messed up my workflow. I keep trying to get development to at least use edit rather than the in context edits, but that is hit or miss. I get ~5 emails for everyone 1 email that is relevant. Very frustrating. The mail app on my iPhone is grouping them fine.
Like I said, this worked before. I don't know if the change was due to some patch in Office, or an update from JIRA.
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