Paul's Down-Home Page

I am an early adopter (but then if you’ve been reading this blog for more than 10 minutes, you knew that already). Recently, two fairly new pieces of technology have been working together in a, shall we say, unexpected way.

First is Outlook 2010, which I’ve been running for some time. Overall I like it a lot; it performs well, it supports multiple Exchange accounts, and it has lots of grace notes (like the configurable "Quick Steps" feature) that make using it both easier and more pleasant than earlier versions.

Second is the newest release (3.1) of the Facebook client for the iPhone. It has the option to automatically sync Facebook data (including profile links and pictures) for contacts it finds in your iPhone address book.

Put these two together, and what do you get? Pictures of people you don’t really know showing up in Outlook, like this:

Yes, that’s right: any time I exchange mail with someone whose e-mail address is registered with Facebook, I get their picture! In this case, a college student bought a book I had listed on Amazon, and she was writing to ask whether I’d shipped it or not. Imagine my surprise to see a picture of her and her two BFFs (at least that’s who I assume the other two girls are.)

What’s making that happen? Outlook 2010 has a feature called "Suggested Contacts" that automatically adds the e-mail addresses of people you correspond with to a new "Suggested Contacts" folder. This replaces the old .nk2 file that earlier versions used for nickname autocompletion. Unfortunately, Suggested Contacts appears to most applications (well, the ones that aren’t Outlook 2010) as a regular Contacts folder. On the iPhone (and in Mail.app) that means that people you’ve exchanged e-mail with show up in your contact list until you manually purge them.

The Facebook app on the iPhone is trying to be helpful, so it looks for people in your address book—which now includes the contents of Suggested Contacts—and downloads their pictures. Ta da! Instant confusion.

The contact-picture feature is one of my favorite Outlook 2010 enhancements, so I’m not going to turn it off. Likewise, having up-to-date pictures of my actual Facebook friends is a neat feature, so i"m leaving it on as well. For now, that means that I’m stuck occasionally seeing pictures of people I don’t know—part of the price for being an early adopter, I guess.

Now this is a neat idea; I wish I’d thought of it.

Microsoft’s released the Exchange 2010 Deployment Assistant, a web site that interviews you about what your deployment plans are and then assembles a customized subset of the Exchange 2010 documentation for you.

You start by indicating whether you’re moving from an existing deployment (either 2003, 2007, or mixed) or creating a new one. Once you’ve done that, you answer questions (such as "will you be using public folders?" or "do you plan to deploy unified messaging?"), and you get a checklist like this one:

The tool is clearly still in the early stages of development; it only includes content for upgrading from pure Exchange 2003 environments. However, it’s an improvement over the old deployment wizard in two major ways. First, it’s more highly customized for your particular migration plans. Second, it gives you a single point of access to everything you need to know about a particular topic (like installing a mailbox server).

I’m looking forward to seeing how the product group improves the tool in future releases. Check it out and you’ll see what I mean.

I’ll ignore the easy route of poking fun at Cisco’s massive product introduction. 61 collaboration and communications product? That’s not a strategy; it’s a yard sale. Even IBM does a better job at acquiring others’ technologies and making them into something cohesive (well, except for Workplace Messaging, but why beat that dead horse again?) Instead, I want to dig a little deeper into Cisco’s announcement of Cisco WebEx Mail—not too deep, since I haven’t had time to watch the videos from Cisco’s virtual launch event. They won’t play on Windows 7, using either IE8 or Firefox 3.5. Oh well. (Also: Cisco, your video portal is weak sauce compared to PKS. Call 3Sharp, stat!)

WebEx Mail is based on Cisco’s PostPath acquisition. After the purchase, my guess was that Cisco would turn PostPath into an e-mail appliance that could nestle in a rack next to other Cisco gear. Turns out I was wrong; instead, Cisco’s turned it into a hosted service. This is an interesting play for a couple of reasons. One is that a historic PostPath weakness is the admin experience. Keeping customers from being exposed to that level of awfulness is a great idea. Another is that offering a black-box hosting solution plays to PostPath’s strength: mostly seamless interop with Outlook.

If you compare the last release of PostPath (which emulated Exchange 2003) to Exchange 2007, you could argue that some of the storage and performance improvements in Exchange 2007 were obviated by the fact that PostPath uses a completely different method of message storage. However, in the testing Tim and I did, we documented lots of other Exchange 2007 improvements (PowerShell, CCR/SCR, full Exchange ActiveSync support, and MRM, to name a few) that PostPath didn’t have.

In the interval since Cisco bought PostPath, I’m sure they’ve made improvements. So has Microsoft, though. Exchange 2010 offers a number of hosting-oriented features, but the biggest is probably the option to have seamless interoperability between hosted Exchange and on-premises servers. Being able to do an online mailbox move between the cloud and your own server room is pretty darn useful. I haven’t seen enough details to tell whether Cisco’s claim "frictionless migration" is real or baloney. In addition, Exchange 2010 offers a very powerful set of confidentiality tools: between Outlook protection rules and IRM in transport rules, you can easily set up an environment such that your hosters can’t read your mail, no matter their motivation.

Another area where WebEx Mail appears to fall short: integration. Of course, we’re all familiar with the integration between Outlook, Communicator, Exchange, SharePoint, and other MS products. Less familiar is the fact that you can take advantage of that integration using Microsoft’s BPOS hosting offering, too. Does Cisco have an equivalent? Not that I can tell. Are they working on one? My guess is yes, but delivering a seamless experience is not an easy problem to solve, and Cisco is hampered by having lots of individual products that have to be sewn together. Seems like MS has a clear lead in this area.

Props to Cisco for describing their security infrastructure, though. This white paper makes clear what security measures they use for various parts of their system. In particular, they call out security policy, physical security, and auditing, and they mention that they follow the NIST STIGs for server hardening. This is just the kind of detail that we need to evaluate cloud-based service security, and it stands in sharp contrast to Google, which says nothing about their security. Even Microsoft basically says "hey, we’re SAS70 certified, trust us"—they can do better.

Bonus interlude: Windows 7? What’s that? Cisco apparently never heard of it.

One last thought: terrible name. Most people who know the WebEx brand associate it with conferencing, not e-mail. Most people who know the Cisco name don’t associate it with WebEx (and probably vice versa). Surely Cisco could have done better than this. I’m reminded of the old Jerry Pournelle jape about AT&T: if they bought Kentucky Fried Chicken they’d advertise it as "hot, dead chicken."

I’ll have more to say about WebEx Mail once I’ve had a chance to dig into it more thoroughly.