Category Archives: UC&C

US lawyers and Office 365

Every field has its own unique constraints; the things the owner of a small manufacturing business worries about will have some overlap, but many differences, compared to what the CEO of a multi-billion-dollar energy company is concerned with. The legal industry is no exception; one major area of concern for lawyers is ethics. No, I don’t mean that they’re concerned about not having any. (I will try to refrain from adding any further lawyer jokes in this post unless, you know, they’re funny).

Disclaimer: I am not a lawyer. This is not legal advice. Seriously.

The entire US legal system is based on a number of core principles, including that of precedent, or what laymen might call “tradition”. For that reason, as well as the stiff professional penalties that may result from a finding of malpractice or incompetence, many in the legal profession have been slower to embrace technology than their peers in other industries. When there is no settled precedent to answer a question, someone has to generate precedent, often by taking a case to court. Various professional standards bodies can generate opinions that are considered to be more or less binding on their members, too. To cite one example of what I mean, here’s what the Lawyers’ Professional Responsibility Board of the state of Minnesota has to say about one small aspect of legal ethics, the safeguarding and use of metadata:

…a lawyer is ethically required to act competently to avoid improper disclosure of confidential and privileged information in metadata in electronic documents.

That seems pretty straightforward; the body responsible for “the operation of the professional responsibility system in Minnesota” issued an opinion calling for attorneys in that state to safeguard metadata and refrain from using it in ways that conflict with their other ethical obligations. With that opinion now extant, lawyers in Minnesota can, presumably, be disciplined for failing to meet that standard.

With that as background, let me share this fascinating link: a list of ethics opinions related to the use of cloud services by lawyers and law firms. (I found the list at Sharon Nelson’s excellent “Ride the Lightning” blog, which I commend to your attention.)

Let that sink in for a minute: some of the organizations responsible for setting ethical standards for lawyers in various states are weighing in on the ethics of legal use of cloud services.

This strikes me as remarkable for several reasons. Consider, for example, that there don’t seem to be similar guidelines for e-mail admins, or professional engineers, or cosmetologists, or any other profession that I can think of. In pretty much every other market, if you want to use cloud services, feel free! Oh, sure, you may want to consider the ramifications of putting sensitive or protected data into the cloud, especially if you have specific requirements around compliance or governance. By and large, though, no one is going to punish you for using cloud services in your business if that choice turns out to be inappropriate. On the other hand, if you’re a lawyer, you can be professionally liable for failing to protect your clients’ confidentiality, as might happen in case of a data breach at your cloud provider.

The existence of these opinions, then, means that in at least 14 states, there are now defined standards that practitioners are expected to follow when choosing and using cloud services. For example, the Alabama standard (which I picked because it is simple, because I live in Alabama, and because it was first in the alphabetical list) says:

…a lawyer may use “cloud computing” or third-party providers to store client data provided that the attorney exercises reasonable care in doing so… The duty of reasonable care requires the lawyer to become knowledgeable about how the provider will handle the storage and security of the data being stored and to reasonably ensure that the provider will abide by a confidentiality agreement in handling the data. Additionally, because technology is constantly evolving, the lawyer will have a continuing duty to stay abreast of appropriate security safeguards that should be employed by the lawyer and the third-party provider. If there is a breach of confidentiality, the focus of any inquiry will be whether the lawyer acted reasonably in selecting the method of storage and/or the third party provider.

The other state opinions are generally similar in that they require an attorney to act with “reasonable care” in choosing a cloud service provider. That makes Microsoft’s recent relaunch of the expanded Office 365 Trust Center a great move: it succinctly addresses “appropriate security safeguards” that are applied throughout the Office 365 stack. Reading it will give you a solid grounding in the physical. technical, and operational safeguards that Microsoft has in place.

Compared to its major SaaS competitors, Microsoft’s site has more breadth and depth about security in Office 365, and it’s written in an approachable style that is appropriate for non-technical people… including attorneys. In particular, the top-10 lists provide easily digestible bites that help to reassure customers that there data, and metadata, are safe within Microsoft’s cloud. By comparison, the Google Apps security page is limited in both breadth and depth; the Dropbox page is laughable, and the Box.net page is basically a quick list of bullets without much depth to back them up.

The Office 365 Trust Center certainly provides the information necessary for an attorney to “become knowledgeable about how the provider will handle the storage and security of the data being stored”, and it is equally useful for the rest of us because we can do the same thing. If you haven’t already done so, it’s worth a few minutes of your time to go check it out; you’ll probably come away with a better idea of the number and type of security measures that Microsoft applies to Office 365 operations, which will help you if a) you go to law school and/or b) you are considering moving to Office 365.

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Exchange Server and Azure: “not now” vs “never”

Wow, look what I found in my drafts folder: an old post.

Lots of Exchange admins have been wondering whether Windows Azure can be used to host Exchange. This is to be expected for two reasons. First, Microsoft has been steadily raising the volume of Azure-related announcements, demos, and other collateral material. TechEd 2014 was a great example: there were several Azure-related announcements, including the availability of ExpressRoute for private connections to the Azure cloud and several major new storage improvements. These changes build on their aggressive evangelism, which has been attempting, and succeeding, to convince iOS and Android developers to use Azure as the back-end service for their apps. The other reason, sadly, is why I’m writing: there’s a lot of misinformation about Exchange on Azure (e.g. this article from SearchExchange titled “Points to consider before running Exchange on Azure”, which is wrong, wrong, and wrong), and you need to be prepared to defuse its wrongness with customers who may misunderstand what they’re potentially getting into.

On its face, Azure’s infrastructure-as-a-service (IaaS) offering seems pretty compelling: you can build Windows Server VMs and host them in the Azure cloud. That seems like it would be a natural fit for Exchange, which is increasingly viewed as an infrastructure service by customers who depend on it. However, there are at least three serious problems with this approach.

First: it’s not supported by Microsoft, something that the “points to consider” article doesn’t even mention. The Exchange team doesn’t support Exchange 2010 or Exchange 2013 on Azure or Amazon EC2 or anyone else’s cloud service at present. It is possible that this will change in the future, but for now any customer who runs Exchange on Azure will be in an unsupported state. It’s fun to imagine scenarios where the Azure team takes over first-line support responsibility for customers running Exchange and other Microsoft server applications; this sounds a little crazy but the precedent exists, as EMC and other storage companies did exactly this for users of their replication solutions back in Exchange 5.5/2000 times. Having said that, don’t hold your breath. The Azure team has plenty of other more pressing work to do first, so I think that any change in this support model will require the Exchange team to buy in to it. The Azure team has been able to get that buy-in from SharePoint, Dynamics, and other major product groups within Microsoft, so this is by no means impossible.

Second: it’s more work. In some ways Azure gives you the worst of the hosted Exchange model: you have to do just as much work as you would if Exchange were hosted on-premises, but you’re also subject to service outages, inconsistent network latency, and all the other transient or chronic irritations that come, at no extra cost, with cloud services. Part of the reason that the Exchange team doesn’t support Azure is because there’s no way to guarantee that any IaaS provider is offering enough IOPS, low-enough latency, and so on, so troubleshooting performance or behavior problems with a service such as Azure can quickly turn into a nightmare. If Azure is able to provide guaranteed service levels for disk I/O throughput and latency, that would help quite a bit, but this would probably require significant engineering effort. Although I don’t recommend that you do it at the moment, you might be interested in this writeup on how to deploy Exchange on Azure; it gives a good look at some of the operational challenges you might face in setting up Exchange+Azure for test or demo use.

Third: it’s going to cost more. Remember that IaaS networks typically charge for resource consumption. Exchange 2013 (and Exchange 2010, too) is designed to be “always on”. The workload management features in Exchange 2013 provide throttling, sure, but they don’t eliminate all of the background maintenance that Exchange is more-or-less continuously performing. These tasks, including GAL grammar generation for Exchange UM, the managed folder assistant, calendar repair, and various database-related tasks, have to be run, and so IaaS-based Exchange servers are continually going to be racking up storage, CPU, and network charges. In fairness, I haven’t estimated what these charges might be for a typical test-lab environment; it’s possible that they’d be cheap enough to be tolerable, but I’m not betting on it, and no doubt a real deployment would be significantly more expensive.

Of course, all three of these problems are soluble: the Exchange team could at any time change their support policy for Exchange on Azure, and/or the Azure team could adjust the cost model to make the cost for doing so competitive with Office 365 or other hosted solutions. Interestingly, though, two different groups would have to make those decisions, and their interests don’t necessarily align, so it’s not clear to me if or when we might see this happen. Remember, the Office 365 team at Microsoft uses physical hardware exclusively for their operations.

Does that mean that Azure has no value for Exchange? On the contrary. At TechEd New Orleans in June 2013, Microsoft’s Scott Schnoll said they were studying the possibility of using an Azure VM as the witness server for DAGs in Exchange 2013 CU2 and later. This would be a super feature because it would allow customers with two or more physically separate data centers to build large DAGs that weren’t dependent on site interconnects (at the risk, of course, of requiring always-on connectivity to Azure). The cost and workload penalty for running an FSW on Azure would be low, too. In August 2013, the word came down: Azure in its present implementation isn’t suitable for use as an FSW. However, the Exchange team has requested some Azure functionality changes that would make it possible to run this configuration in the future, so we have that to look forward to.

Then we have the wide world of IaaS capabilities opened up by Windows Azure Active Directory (WAAD), Azure Rights Management Services, Azure Multi-Factor Authentication, and the large-volume disk ingestion program (now known as the Azure Import/Export Service). As time passes, Microsoft keeps delivering more, and better, Azure services that complement on-premises Exchange, which has been really interesting to watch. I expect that trend to continue, and there are other, less expensive ways to use IaaS for Exchange if you only want it for test labs and the like. More on that in a future post….

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Getting ready for TechEd 2014

Wow, this snuck up on me! TechEd 2014 starts in 10 days, and I am nowhere near ready.

A few years ago, I started a new policy: I only attend TechEd to speak, not as a general attendee or press member; the level of technical content for the products I work with has declined steadily over the years. This is to be expected; in a four-day event, there’s a finite number of sessions that Microsoft can present, and as they add new products, every fiefdom must have its due. There are typically around 30 sessions that involve unified communications in some way; that number has remained fairly constant since 2005 or so. Over the last several years, the mix of sessions has changed to accommodate new versions of Exchange, Lync, and Office 365, but the limited number of sessions means that TechEd can’t offer the depth of MEC, Exchange Connections, or Lync Conference. This year there are 28 Exchange-related sessions, including several that are really about Office 365— so about 25% the content of MEC.

I can’t keep track of how many previous TechEd events I’ve been to; if you look at the list, you’ll see that they tend to be concentrated in a small number of cities and so they all kind of blend together. (Interestingly, this 2007 list of the types of attendees you see at TechEd is still current.) The most memorable events for me have been the ones in Europe (especially last year’s event in Madrid, where I’d never been before).

This year I was asked to pinch-hit and present OFC-B318, “What’s New in Lync Mobile.” That’s right— so far this year, I have presented on Lync at Lync Conference and MEC, plus this session, plus another Lync session at Exchange Connections! If I am not careful I’ll get a reputation. Anyway, I am about ready to dive into shining up my demos, which will feature Lync Mobile on a variety of devices— plus some special guests will be joining me on stage, including my favorite Canadian, an accomplished motorcycle rider, and a CrossFitter. You’ll have to attend the session to find out who these people are though: 3pm, Monday the 12th— see you there! I’ll also be working in the Microsoft booth area at some point, but I don’t know when yet; stay tuned for updates.

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Speaking at Exchange Connections 2014

I’m excited to say that I’ll be presenting at Exchange Connections 2014, coming up this fall at the Aria in Las Vegas.

Tony posted the complete list of speakers and session titles a couple of days ago. I’m doing three sessions:

  • “Who Wears the Pants In Your Datacenter: Taming Managed Availability”: an all-new session in which the phrase “you’re not the boss of me” will feature prominently. You might want to prepare by reading my Windows IT Pro article on MA, sort of to set the table.
  • “Just Like Lemmings: Mass Migration to Office 365”: an all-new session that discusses the hows and whys of moving large volumes of mailbox and PST data into the service, using both Microsoft and third-party tools. (On the sometimes-contentious topic of public folder migration, I plead ignorance; see Sigi Jagott’s session if you want to know more). There is a big gap between theory and practice here and I plan to shine some light into it.
  • “Deep Dive: Exchange 2013 and Lync 2013 Integration” covers the nuts and bolts of how to tie Lync and Exchange 2013 together. Frankly, if you saw me present on this topic at DellWorld, MEC, or Lync Conference, you don’t need to attend this iteration. However, every time I’ve presented it, the room has been packed to capacity, so there’s clearly still demand for the material!

Exchange Connections always has a more relaxed, intimate feeling about it than the bigger Microsoft-themed conferences. This is in part because it’s not a Microsoft event and in part because it is considerably smaller. As a speaker, I really enjoy the chance to engage more deeply with the attendees than is possible at mega-events. If you’re planning to be there, great— and, if not, you should change your plans!

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MEC 2014 wrap-up by the numbers

The MEC 2014 conference team sent out a statistical summary of the conference to speakers, and it makes for fascinating reading. I wanted to share a few of the highlights of the report because I think it makes some really interesting points about the state of the Exchange market and community.

First: the 101 sessions were attended by a total of 13,079 people. The average attendance across all sessions was 129, which is impressive (though skewed a bit by the size of some of the mega-sessions; Microsoft had to make a bet that lots of people would attend these sessions, which they did!). In terms of attendance, the top 10 sessions were mostly focused on architecture and deployment:

  • Exchange Server 2013 Architecture
  • Ready, set, deploy: Exchange Server 2013
  • Experts Unplugged: Exchange Top Issues – What are they and does anyone care or listen?
  • Exchange Server 2013 Tips & Tricks
  • The latest on High Availability & Site Resilience
  • Exchange hybrid: architecture and deployment
  • Experts Unplugged: Exchange Deployment
  • Exchange Server 2013 Transport Architecture
  • Exchange Server 2013 Virtualization Best Practices
  • Exchange Design Concepts and Best Practices
RS IV, not life size To put this in perspective, the top session on this list had just over 600 attendees and the bottom had just under 300. Overall attendance to sessions on the architecture track was about double that of the next contender, the deployment and migration track. That tells me that there is still a large audience for discussions of fundamental architecture topics, in addition to the day-in, day-out operational material that we’d normally see emerging as the mainstay of content at this point in the product lifecycle.Next takeaway: Tim McMichael is a rock star. He captured the #1 and #2 slots in the session ratings, which is no surprise to anyone who’s ever heard him speak. I am very hopeful that I’ll get to hear him speak at Exchange Connections this year. The overall quality of speakers was superb, in my biased opinion. I’d like to see my ratings improve (more demos!) but there’s no shame in being outranked by heavy hitters such as Tony, Michael, Jeff Mealiffe, Ross Smith IV (pictured at left; not actual size), or the ebullient Kamal Janardhan. MEC provides an excellent venue for the speakers to mingle with attendees, too, both at structured events like MAPI Hour and in unstructured post-session or hallway conversations. To me, that direct interaction is one of the most valuable parts of attending a conference, both as a speaker and because I can ask other speakers questions about their particular areas of expertise.

Third, the Unplugged sessions were very popular, as measured both by attendance numbers and session ratings. I loved both the format and content of the ones I attended, but they depend on having a good moderator— someone who is both knowledgeable about the topic at hand and experienced at steering a group of opinionated folks back on topic when needed. While I am naturally bad at that, the moderators overall did an excellent job and I hope to see more Unplugged sessions at future events. When attendees added sessions to their calendar, the event staff used that as a means of gauging interest and assigning rooms based on the likely number of attendees. However, looking at the data shows that people flocked to sessions based on word-of-mouth and didn’t necessarily update their calendars; I calculated the attendance split by dividing the number of people who attended an actual session by the number who said they would attend. If 100 calendared the session but 50 attended, that would be a 50% split. The average split across all sessions (except one) was 53.8%— not bad considering how dynamic the attendance was. The one session I left out was “Experts Unplugged: Architecture – HA and Storage”, which had a split of 1167%! Of the top 10 splits (i.e. sessions where the largest percentage of people stood by their original plans), 4 were Unplugged sessions.

Of course, MEC was much more than the numbers, but this kind of data helps Microsoft understand what people want from future events, measured not just by asking them but by observing their actual preferences and actions. I can’t wait to see what the next event, whenever it may be, will look like!

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Microsoft updates Recoverable Items quota for Office 365 users

Remember when I posted about the 100GB limit for Personal Archive mailboxes in Office 365? It turns out that there was another limit that almost no one knew about, primarily because it involves mailbox retention. As of today, when you put an Office 365 mailbox on In-Place Hold, the size of the Recoverable Items folder is capped at 30GB. This is plenty for the vast majority of customers because a) not many customers use In-Place Hold in the first place and b) not many users have mailboxes that are large enough to exceed the 30GB quota. Multiply two small numbers together and you get another small number.

However, there are some customers for whom this is a problem. One of the most interesting things about Office 365 to me is the speed at which Microsoft can respond to their requests by changing aspects of the service architecture and provisioning. In this case, the Exchange team is planning to increase the size of the Recoverable Items quota to 100GB. Interestingly, they’re actually starting by increasing the quota for user mailboxes that are now on hold— so from now until July 2014, they’ll be silently increasing the quota for those users. If you put a user on hold today, however, their quota may not be set to 100GB until sometime later.

If you need an immediate quota increase, or if you’re using a dedicated tenant, you’ll still have to use the existing mechanism of filing a support ticket to have the quota increased.

There’s no public post on this yet, but I expect one shortly. In the meantime, bask in the knowledge that with a 50GB mailbox, 100GB Personal Archive, and 100GB Recoverable Items quota, your users probably aren’t going to run out of mailbox space any time soon.

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Two-factor authentication for Outlook and Office 2013 clients

I don’t usually put on my old man hat, but indulge me for a second. Back in February 2000, in my long-forgotten column for TechNet, here’s what I said about single-factor passwords:

I’m going to let you in on a secret that’s little discussed outside the security world: reusable passwords are evil.

I stand by the second half of that statement: reusable passwords are still evil, 14 years later, but at least the word is getting out, and multi-factor authentication is becoming more and more common in both consumer and business systems. I was wrong when I assumed that smart cards would become ubiquitous as a second authentication factor; instead, the “something you have” role is increasingly often filled by a mobile phone that can receive SMS messages. Microsoft bought into that trend with their 2012 purchase of PhoneFactor, which is now integrated into Azure. Now Microsoft is extending MFA support into Outlook and the rest of the Office 2013 client applications, with a few caveats. I attended a great session at MEC 2014 presented by Microsoft’s Erik Ashby and Franklin Williams that both outlined the current state of Office 365-integrated MFA and outlined Microsoft’s plans to extend MFA to Outlook.

First, keep in mind that Office 365 already offers multi-factor authentication, once you enable it, for your web-based clients. You can use SMS-based authentication, have the service call you via phone, or use a mobile app that generates authentication codes, and you can define “app passwords” that are used instead of your primary credentials for applications— like Outlook, as it happens— that don’t currently understand MFA. You have to enable MFA for your tenant, then enable it for individual users. All of these services are included with Office 365 SKUs, and they rely on the Azure MFA service. You can, if you wish, buy a separate subscription to Azure MFA if you want additional functionality, like the ability to customize the caller ID that appears when the service calls your users.

With that said, here’s what Erik and Franklin talked about…

To start with, we have to distinguish between the three types of identities that can be used to authenticate against the service. Without going into every detail, it’s fair to summarize these as follows:

  • Cloud identities are homed in Azure Active Directory (AAD). There’s no synchronization with on-premises AD because there isn’t one.
  • Directory sync (or just “dirsync”) uses Microsoft’s dirsync tool, or an equivalent third-party tool, to sync an on-premises account with AAD. This essentially gives services that consume AAD a mostly-read-only copy of your organization’s AD.
  • Federated identity uses a federation broker or service such as Active Directory Federation Services (AD FS), Okta, Centrify, and Ping to allow your organization’s AD to answer authentication queries from Office 365 services. In January 2014 Microsoft announced a “Works With Office 365 – Identity” logo program, so if you don’t want to use AD FS you can choose another federation toolset that better meets your requirements.

Client updates are coming to the Office 2013 clients: Outlook, Lync, Word, Excel,  PowerPoint, and SkyDrive Pro. With these updates, you’ll see a single unified authentication window for all of the clients, similar (but not necessarily identical) to the existing login window you get on Windows when signing into a SkyDrive or SkyDrive Pro library from within an Office client. From that authentication window, you’ll be able to enter the second authentication factor that you received via phone call, SMS, or authentication app. During the presentation, Franklin (or maybe Erik?) said “if you can authenticate in a web browser, you can authenticate in Office clients”— very cool. (PowerShell will be getting MFA support too, but it wasn’t clear to me exactly when that was happening).

These client updates will also provide support for two specific types of smart cards: the US Department of Defense Common Access Card (CAC) and the similar-but-civilian Personal Identity Verification (PIV) card. Instead of using a separate authentication token provided by the service, you’ll plug in your smart card, authenticate to it with your PIN, and away you go.

All three of the identity types of these methods provide support for MFA; federated identity will gain the ability to do true single sign-on (SSO) jn Office 2013 clients, which will be a welcome usability improvement. Outlook will get SSO capabilities with the other two identity types, too.

How do the updates work? That’s where the magic part comes in. The Azure Active Directory Authentication Library (ADAL) is being extended to provide support for MFA. When the Office client makes a request to the service the service will return a header that instructs the client to visit a security token service (STS) using OAuth. At that point, Office uses ADAL to launch the browser control that displays the authentication page, then, as Erik puts it, “MFA and federation magic happens transparent to Office.” If the authentication succeeds, Office gets security tokens that it caches and uses for service authentication. (The flow is described in more detail in the video from the session, which is available now for MEC attendees and will be available in 60 days or so for non-attendees).

There are two important caveats that were a little buried in the presentation. First is that MFA in Outlook 2013 will require the use of MAPI/HTTP. More seriously, MFA will not be available to on-premises Exchange 2013 deployments until some time in the future. This aligns with Microsoft’s cloud-first strategy, but it is going to aggravate on-premises customers something fierce. In fairness, because you need the MFA infrastructure hosted in the Microsoft cloud to take advantage of this feature, I’m not sure there’s a feasible way to deliver SMS- or voice-based MFA for purely on-prem environments, and if you’re in a hybrid, then you’re good to go.

Microsoft hasn’t announced a specific timeframe for these updates (other than “second half calendar 2014”), and they didn’t say anything about Mac support, though I would imagine that the rumored v.next of Mac Office would provide this same functionality. The ability to use MFA across all the Office client apps will make it easier for end users, reducing the chance that they’ll depend solely on reusable passwords and thus reducing the net amount of evil in the world— a blessing to us all.

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