Moving to the Cloud Part 2: Mostly Sunny

In part 1 of this now multi-part series (who knew?), I discussed my initial attempts at moving my digital life into the cloud, including files, music, photos, notes, task lists, mail, contacts, calendar and PC games.There were some issues, however, and some things that I forgot, so we have part 2.

Before we get to that, however, it’s interesting (for me, at least) to think about why it’s important to be able to move things into the cloud. Lots of vendors are busy making this possible, but why? There are backup reasons, of course, so that a fire or other natural disaster doesn’t wipe out all of the family pictures. There are also the ease of sharing, since email makes a very poor file sharing system. Also, multi-device access is certainly useful, since the world has moved into a heterogeneous OS world again as smartphones and tablets take their place at the table with PCs.

For me, however, moving my data into the cloud is about freedom.

The cloud enables me to get myself bootstrapped with data associated with my personal or business life, using whatever device or OS I feel like using that day. It provides me freedom of location or vendor.

The cloud is still forming, however, so hasn’t really been able to make this a seamless experience, which is why I’m onto part 2 of this series.

Mail, Contacts and Calendar

Hotmail is a fine system for online access to mail, contacts and calendar that integrates well with Windows Phone 7. However, the integration with desktop Outlook and my custom domain isn’t good enough yet to rely on. The primary problem was the Hotmail Outlook Connector, which isn’t ready yet for prime time. It worked great with calendar and contacts, but fell down badly when it came to large email folders that I moved from my PST file. It never showed the sync’ing progress as complete, which made me uncomfortable that it never actually completed sync’ing and therefore my data wasn’t safe. Also, when I sent an email from Hotmail, either via the web or via Outlook, it showed the reply address as hotmail_44fe54cff788bdde@live.com. I assume the latter would’ve been fixed with Windows Live custom domains, but the former was the real deal-killer for me.

Also, I heard that Google Apps is the way to go, but that also requires some special software to enable sync’ing with desktop Outlook – I wanted something that was native to both Outlook 2010 and Windows Phone 7. Further, it cost money, so if I was going to pay, I wanted something that Microsoft was going to integrate well with.

So, I bit the bullet and hooked myself with the latest in hosted Exchange – Microsoft Office 365. That’s what I’m using now and just like the on-premise Exchange that worked great for me as a Microsoft employee, I’ve been very happy with it. However, because of the way I was using it, it was a pain to configure properly for use in hosting my csells@sellsbrothers.com email.

The easy way to configure Office 365 is to let it be the DNS name manager, which lets it manage everything for you, including your web site (via SharePoint), your mail, your Lync settings and any future service they care to tack on. However, that doesn’t work for me, since I didn’t want to move my 16-year-old web site into SharePoint (duh). Instead, I wanted to leave my DNS name manager at securewebs.com, which has been a fabulous web hosting ISP for me.

A slightly harder way to configure Office 365 for use with your domain is to only be used for selective services, e.g. set the MX record for mail, but don’t mess with the CNAME record for your web site. This would’ve been nice, too, except I don’t want to move all of the email accounts on sellsbrothers.com – only csells. Why? Well, that’s a family matter.

Over the years at family gatherings, to seem geek cool, I’ve offered free email boxes to my relatives. “Oh? You’re moving to another ISP again? Why don’t you move your email to sellsbrothers.com and then you can keep the same email address forever! And the best part is that it’s free!”

Now, of course, I’d recommend folks get an email address on hotmail or gmail, but this all started before the email storage wars back when you needed an actual invitation to set up a gmail.com account. Now I’ve got half a dozen family members with “permanent” and “free” email boxes and I don’t want to a) move them, b) charge them or c) pay for them myself on Office 365.

As cheap as you might think I am, it’s really migration that I worry most about – having successfully gotten them set up on their phones and PCs with their current email host, I don’t want to do that again for Outlook or migrate their email. Maybe it’s easy, maybe it’s hard. We’ll never know ‘cuz I’m not doing it!

So now, I have to make csells@sellsbrothers.com sync with Office 365 and leave everyone else alone. This is the hardest way to use Office 365 and involved the following:

• Set up a custom domain in Office 365: sellsbrothers.onmicrosoft.com
• Add myself as a user: csells@sellsbrothers.onmicrosoft.com
• Verify that I own sellsbrothers.com by asking securewebs.com support to add a DNS TXT record as specified by Office 365 (this took two weeks and a dozen emails)
• Make csells@sellsbrothers.com the primary email on that account
• Make csells@sellsbrothers.com the From address by removing csells@sellsbrothers.onmicrosoft.com and adding it back again
• Configure my ISP email (SmarterMail) to forward csells@sellsbrothers.com email to csells@sellsbrothers.onmicrosoft.com (I’m not also deleting the email on my ISP account yet when it forwards, but eventually I plan to)
• Login to my Outlook Web Access account on http://mail.office365.com
• Find my Outlook host name via Help | About | Host name (ch1prd0502.outlook.com) for use as my Outlook server on my Windows Phone 7 (along with my From email address: csells@sellsbrothers.com)
• Stumbling onto the right technical forum post to figure out how to configure desktop Outlook 2010 using advanced settings:
• Server: ch1prd0502.mailbox.outlook.com (my host name with “mailbox” thrown in)
• User name: csells@sellsbrothers.com (my From address)
• Exchange Proxy Server: ch1prd0502.outlook.com (my Host name again)
• Check both checkboxes to use HTTP first before TCP/IP
• Authentication: Basic Authentication

Obviously, this is a crappy configuration experience, but no amount of manual updates to Outlook provided by the Office 365 site seemed to help. It was nice that the WP7 Outlook was much easier, although I’d really loved to have just told desktop Outlook that I was an Office 365 user and had it figure out all the touchy config settings.

Everything seems solid except one minor annoyance: when I do a Reply All, csells@sellsbrothers.com stays in the list because my mail programs don’t know that my csells@sellsbrothers.com and csells@sellsbrothers.onmicrosoft.com email addresses are logically the same. I assume if I was hosting my MX records at Office 365, this problem, along with the crappy config experience, would go away.

The good news is that I’ve got access to my full range of Mail, Contacts and Calendar from the web, my phone and my desktop, including multi-GB email folders I’ve copied over from my PST file, all for $6/month. Had I to do it over again, I’d have long ago moved my family to hotmail and avoided the config nightmare. I may yet do just that.

Encrypted Files

With my mail et al sorted, my next fix from last time was the lack of confidence in my most sensitive files with Dropbox. Dropbox can be hacked or subpoenaed like anyone else, so I want a client-side encryption solution. Dropbox may someday provide this themselves, but currently they gain a great deal of storage savings by detecting duplicate blocks amongst their users, saving significantly on uploads and storage, which client-side encryption disrupts. In the meantime, I really want an app that encrypts on the client and drops my data into Dropbox, which BoxCryptor does nicely.

In addition to supporting Windows, BoxCryptor also supports MacOS, iOS and Android, although not WP7 yet. Further, it’s free for 2GB and only a $40 one-time fee for unlimited data, so it’s cheap, too.

I also looked at SecretSync, which has a similar cross-platform story and pricing model (although it’s $40/year instead of $40/once), but it requires Java and I don’t put that on my box. For an open source solution, you may be interested in TrueCrypt.

Financial Data

I’m a mint.com user. I like the idea of an all-up look at my finances across 29 online financial accounts. However, as a backup of that data, I wrote a mint.com scraping tool that downloads the CSV transactions export file and digs current snapshot data out of the homepage HTML. The format on the web site is constantly changing of course, so it’s a support problem, but having that data even a little messed up over time is way better than not having it at all, so I’m happy. The data itself goes into CSV files that I can query with LINQPad and that are stored in my Dropbox folder, which keeps them sync’d.

Books and Bookmarks

I can’t believe I missed this last time, but one of the big things I keep in the in the cloud is my set of Amazon Kindle books. I think that the proprietary format and DRM of Kindle materials will eventually open up because of competition, but until then, Amazon has been a great steward of my online books and bookmarks, providing me clients for all new platforms as well as their own e-ink-based hardware. I have an extensive book collection (this is just part of it), but am adding to the physical part of it no more.

Further, in the case that I have the “what the hell was that book I used to have?” moment after I finally truck all of my books off to Powell’s, the Brothers Sells have scanned all of the ISBN numbers from my 500+ books into LibraryThing. I won’t have the books anymore, but at least I’ll be able to browse, refresh my memory and add the books to Kindle on demand. The reason I picked LibraryThing is because it was easy to get all of the book metadata from just an ISBN (so it’s easy to spot data entry errors early), it’s easy to export from in a CSV file and, should I decide, easy to user their API.

App Specifics

In addition to the big categories, several apps keep data important to me:

• Twitter keeps Twitter users I’m following and searches
• Facebook keeps Facebook contacts, which is nice because they can maintain their own contact data for me and I don’t have to be constantly out of data with my copy
• Windows Live Messenger keeps my IM contacts for me, although Facebook has largely replaced that for IM chatting
• As of the latest update, Xbox game state in the cloud for me, although I’m not a big enough gamer that I really need it anywhere else except my home console. I assume in the future, MS will also keep the Xbox games I’ve purchased in the cloud as well
• Hulu keeps a list of several TV shows I like and notifies me when new episodes are available
• Netflix keeps a partial list of movies I’d like to see, but unfortunately not all of them
• I keep my blog posts in an instance of SQL Server maintained on securewebs.com, which I assume they backup regularly. Someday I’ll write the script to pull that data out into my Dropbox just in case. The source code for the site itself is already stored in Dropbox, so I’m set there
• Favorites: I don’t have a good app here, but I’d love it if some app could keep my IE favorites sync’d between my phone and my other computers. Suggestions?

Things Left On The Ground

As you may have surmised, I don’t put a lot of sentimental value in physical things. They’re not nearly as important to me as people, experiences or data. However, there are some things that I’d want to rescue in case of disaster given the chance:

• A few wrist watches that reminds me of a special person or event
• An inscribed copy of The Complete Sherlock Holmes that my grandfather, my father and I have all read
• Inscribed copies of The Hobbit and The Lord of the Rings trilogy that my mother read to me as a child
• A leather bound copy of Batman: The Dark Knight Returns because Frank Miller kicks ass
• Two pieces of marble and maple furniture that my grandfather built to withstand the onslaught from my mother barreling through each room at top speed as a child (I’d have liked to see the first collision of the immovable object and the irresistible force that day!)

As hard as I try, I can’t think of anything else. Should I have to jam, my plan is to place these few items into safe keeping and sell, donate and/or toss the rest.

Where Are We?

As I write this, I’m sitting in a Starbucks in Sandy, OR, 20 minutes from a cabin I’m renting for a few days. When I’m done here, I’ll explore the town, see a movie and make myself some dinner. I won’t worry about my phone, my laptop or my home being lost or destroyed, since 98% of the possessions I deem most valuable are being managed by cloud vendors I trust.

The cloud doesn’t just represent a place to backup or store data – it represents a way of life.

My data stores a lifetime of experiences, people and knowledge. By keeping it safe and available no matter where I go, I gain the freedom to wander, to experience new physical places and new hardware and software solutions, all without being unduly burdened.

Creative work requires a comfortable place to labor filled with the tools and the materials the worker needs to be creative. Today my tools are an Apple MacBook, Windows 7, Office 2010, Visual Studio 2010 and a Samsung Focus. Yesterday those tools were different and I’m sure they’ll be different again tomorrow. However, while other people build up their place with comfortable things around them – a bookshelf for reference, a comfy chair, knick-knack reminders of events or trips – my place is a lifetime of data and anywhere that provides access to electrons and bits.

Having my data safe, secure and available makes me feel comfortable, creative and free.