Outlook's missing picture compression feature

It seems so long ago now, but when Outlook 2003 and Exchange 2003 combined to introduce “cached Exchange mode”, the new capability fundamentally influenced the way people could work with Outlook by insulating the client from the vagaries of network connections. Sure, it didn’t make a lot of difference when you had a nice solid Ethernet connection, but suddenly working on a flaky dial-up link (for those who remember such things) or even Wi-Fi suddenly became a lot easier.

I don’t think it is stressing the point too much to say that without cached Exchange mode, it would be impossible to work with a cloud-based solution such as Exchange Online. Reliable as the Internet is today (in relative terms), there are still too many hiccups, drops, and other unexplained connectivity drops to allow work to proceed smoothly.

Outlook 2003 introduced many other interesting features that I have grown to appreciate over time. For example, drizzle mode synchronization makes it possible for Outlook to keep a complete mailbox synchronized without affecting the responsiveness of the client to user input. And Outlook 2003 was the first client to support RPC-over-HTTP, the basis of Outlook Anywhere (OA). For those who haven’t heard, Exchange 2013 makes OA the only method that Outlook clients can connect to Exchange as RPC/TCP “direct MAPI” connectivity has been removed in Microsoft’s drive to simplify the server. Of course, Outlook 2003 isn’t supported by Exchange 2013 at all. Not because of OA, but rather because it’s time to draw the line under a client that is past its best days.

I haven’t used Outlook 2003 in a long time, but I appreciate its legacy. Recently I wondered where another Outlook 2003 feature was in Outlook’s latest incarnation. When you attach graphic files such as JPEG photos to an Outlook 2003 message, Outlook gives you the choice of sending small, medium, or large format versions of the files. This is a useful feature, especially when grappling with the 10MB-plus photos produced by today’s megapixel-rich cameras. Even though Outlook 2003 was launched at a time when digital cameras were in their infancy, the shrink-on-send feature was still useful.

But I could not find the feature in Outlook 2010 or Outlook 2013. Scott Schnoll has subsequently pointed out to me that the option to compress pictures is buried in Windows Explorer under Sent To... Mail Recipient, which I guess kind of counts... or not. And then Greg Taylor pointed out that an option is buried in the "backstage" area of an Outlook 2013 message if you add a graphic attachment. Not only does this hide the option from most users who never look at the properties of an unsent message, it also removes the ability to tweak the size of the graphic attachment, which I thought was useful.

At MEC, I took the opportunity to quiz some of the Exchange and Outlook engineers where the shrink-on-send feature had gone. Most weren't even aware that such a feature existed, probably because they live in a network-rich environment most of the time and always run the latest software builds. Eventually I found someone who told me that the feature was removed because the Outlook team thought it no longer added any value. It’s good to cut redundant and underused features from software as otherwise programs would swell as large as some of the mailboxes seen today.

I’m sad to see shrink-on-send disappear, or at least become obscured in the mass of features that Outlook now provides. I guess it had its time in the limelight, but sometimes I do wish it was still around when I want to send a smaller version of a photo to someone. I guess I just hate wasting bandwidth and storage!

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