Exchange Online Connected Accounts

When I initially switched over to Exchange Online a couple of weeks ago, I was stoked for the “Connected Accounts” functionality that it offered. The idea of a consolidated inbox sounded too good to be true. Unfortunately that proved to be all too true. This isn’t a total bash on the feature, it’s just not something that really “works” for what I was trying to do with it (and hoped it would be able to do).

So first things first, here is what it does ok… It downloads e-mail from (up to 5) POP/IMAP accounts and puts that mail into your Exchange Inbox. It allows you to send messages “on behalf of” those connected accounts on systems that can handle it. In my trials, for actually sending mail from the connected accounts, Outlook and the Outlook Web Client that is provided were the only systems able to correctly use the connected accounts to send. iOS devices send from the default Exchange account when replying to a message, not the alternate address, and on top of that, you can’t even select the additional addresses as options to send from when creating a new message. So it pretty much doesn’t work at all in the case of iOS.

What it doesn’t do well (at all)… Is provide a transparent layer for multiple e-mail accounts. What I mean by that is that if you have two e-mail addresses, your main Exchange account, lets say and a connected account; If you send an e-mail in Outlook from, it will display to the receiver (depending on their mail client) basically saying the message was sent “on behalf of” Here are some examples of how that looks in a few mail systems.



For someone like myself who is a consultant and has many e-mail addresses and doesn’t necessarily want clients to see e-mails coming from one address when they should be from another, it can be problematic. It can also make for unhappy employers, etc.

Gmail offers some ways around these issues, using “Send mail as” functionality that has a much cleaner implementation and actually allows you to use external SMTP servers to send mail. So no more “on behalf of” in your connected accounts messages. It also allows you to join up POP/IMAP accounts to download messages.

This leads to the logical progression of why didn’t I just use Gmail (and Google Apps) instead of Exchange Online? Well, for me, I like the other features of Exchange, like the Calendar, Contact syncing and just the overall experience of the Exchange System. Also, the overall integration with Outlook is quite nice. The Gmail experience might be up to par now, but in my past experiences, the actual Exchange integration just works better.

So, you might ask next, what did I decide to do? Well, it’s not really a work around, or even some other form of consolidation. What I ended up doing is adding all of my accounts individually to Outlook, on my iPhone and my iPad. And you guessed right, that means a lot of accounts. But, it does offer some benefits… the main one being total segregation of my e-mail accounts, no messages will ever be sent on behalf of another account, etc. In Outlook, utilizing the Favorites section for mail, it allows me to see all of my main inboxes in one place and doesn’t really take away much from the experience. I am one of those Outlook users that is used to using the “Folder List” view, but I’m quickly adapting to mostly using the “Mail” view.

Here is what my favorites list looks, you can see the 3 main inboxes for the accounts I use most frequently at the top.

The main up-in-the-air items that are yet to be determined is the performance hit that Outlook will take, it’s now checking multiple accounts instead of just one Exchange account. And what the impact will be on the battery life of my phone and other mobile devices. My guess is that both Outlook and the mobile devices will take a hit, but hopefully it won’t be too bad.

Hopefully, Microsoft will update the Connected Account functionality sometime sooner rather than later, I know it would make me very happy. But until then, this should get the job done!

What are your thoughts?

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