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Conversation clean up, pictures attached inline, and iPhones

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My company is running Outlook 2010 and transitioning from Blackberries to iPhone 5 devices. I’ve found this interesting behavior/bug when a picture is attached inline (in the message body) of an email. Consider this scenario: Person A attaches a picture inline and sends it out. Person B replies to the message with their iPhone. Person A replies to the reply. Person B uses the conversation clean up (Home tab >Delete group > Clean up> Clean up conversation) function in Outlook.

Unfortunately what happens is the conversation clean up deletes the original message (and attachment). Person B realizes they no longer can view the attachment. This does not happen if the picture is in the attachment line (the paperclip). This also doesn’t happen if person B replies with a Blackberry or with Outlook.

The issue has been duplicated with multiple iPhone 5 models (including an iPhone 4), multiple computers, and multiple user accounts. This affects internal email conversations as well as external (to our clients).

I see 3 causes of this experience:

  • This is by design. It could be that this is the intended way that iPhones reply to messages and the intended way Outlook’s conversation clean up feature works.
  • This is a setting. On the iPhone side, I’ve been unable to find a setting that affects this behavior. On the Outlook side, I’ve verified that under File> Options> Mail>Conversation Clean up there is a check next to “When a reply modifies a message, don’t remove the original”.
  • This is a bug in the iPhone software or Outlook software.

Can anyone confirm they have the same issue? Is this a design feature, setting or bug?

I am posting this on Apple’s and Microsoft support forums since I cannot categorize this as either an Outlook or iPhone issue.

Thanks,

Andrew


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