Using Microsoft's Ecosystem: The Good, Bad, and Ugly


I used to have devices and use services belonging to all three ecosystems: Apple's, Google's, and Microsoft's. Some stuff synced beautifully across all devices, others synced with a somewhat hacky solution, and finally some stuff just stayed in one ecosystem.

At one point, my contacts became a disaster scattered across Google, my phone, and Outlook, so I finally threw my hands up and started consolidating all my stuff under one roof, hoping that I won't run into such issues if I stayed in one playground. Given that I liked Windows, and found Office absolutely critical (especially OneNote), over the next few months, I moved my stuff to Microsoft's arena. I got rid of my Android and got a Windows Phone and moved my personal mail and contacts from Gmail to Hotmail (which to my delight had improved a ton, in someways besting even Gmail). Around that time, the new Skydrive launched and I took advantage of that. My new Hotmail ID also became my primary XBox Live account. Overall, life was good.

So What Has Worked?

Documents. ALL of them.

Right after I installed Skydrive on my Windows 7 PC, I made new folders in my Skydrive folder for Documents and Pictures, added those to the respective Libraries in Windows 7, and made those the default file save locations in the respective libraries.

I had about 8GB of files in my old My Documents library. Swoop: all that went into the Skydrive section. Now, Skydrive kept ALL my entire My Documents library in sync with the cloud.

Am I at a friend's computer and I need a file? Load Skydrive in the browser. Do I need to look at a PDF I saved earlier? Launch Skydrive on my phone. I soon plan to get a desktop too, and I can see how it will be pretty awesome to have ALL my documents constantly in sync between the two computers and the cloud.

Skydrive's 7GB free, and additional 20GB for $10 a year (as opposed to $10 a month as with Dropbox) makes keeping ALL your stuff synced super affordable. This allows me to not have to remember to put stuff I may need in my tiny synced folder (as was the case with Dropbox), since everything by default is saved in my humongous Skydrive folder. (I was lucky enough to have an old Skydrive account with 25GB free, so I actually get 45GB for $10/year).


I had about 7GB of pictures that are also now on Skydrive. I keep my pictures sorted by folders titled "YYYY/MM/DD - Event Name" in my library. Picture syncing works identical to Documents, except of course, it uses the Pictures library instead of the Documents library. Additionally, Windows Phone's support for Pictures on Skydrive is just excellent: accessible from any library, any program that wants to attach a picture, etc. All my pictures, everywhere, all the time.

Hotmail Email & Contacts

Hotmail has actually been great for my personal email. I actually have a custom domain ( that I bought for a cheap $10/year from Namecheap. Along with Windows Live Custom Domain, I was able to use as my email ID. This is also my Windows Live ID. Having a custom domain is not just cool, it saves the unfortunate potential embarrassment when I hand out my email ID from people who think Hotmail IDs should be left in the 90s. Additionally, if I ever switch email providers again now, my email ID will move with me: saving me the pain of telling everyone a new email address.

Windows Live/Hotmail is also really good with handling contacts. My phone also does a stupendous job of pulling in contact information I have in Hotmail and combining it with info available on LinkedIn and Facebook.

My Windows Phone works really well, syncing Hotmail email and contacts. It also pulls in my information from my work Microsoft Exchange/Outlook.

Google Chat remains something that I use since my friends are on it, but I've always used Trillian (a desktop program) to keep me logged into GChat and Facebook chat, so I don't really miss that functionality of using Gmail on the web.

Weak Links:

Outlook - Hotmail Linking (this should improve with Office 15)

I love Outlook. Having mail synced to your computer, as opposed to having to work through a web browser, means you can breeze through mail, calendar, etc. with the speed of a desktop application. I currently use Outlook on my laptop with my work email, but not for Hotmail. Why not?

Because currently, to sync Outlook to Hotmail, you need a little Microsoft addon called "Outlook Social Connector". The addon is great when it works, but it's slow to sync, and often comes up with odd errors, particularly with syncing contacts. Now keeping work and personal email in two separate apps (Outlook and Hotmail on the web) hasn't been bad at all, but it would be nice to use the power of Outlook to go through my personal mail too. I'm not too concerned about this though, as Paul Thurrot's reported that the social connector is going away and Outlook 15 to be launched this fall will have in built support for Hotmail (similar to how Windows Phone can connect to both Exchange and Hotmail). That should improve this connection by leaps and bounds since the current buggy social connector is built on old technology.

Windows Phone - Lack of a few apps

I didn't say Windows Phone, I said the lack of specific apps. To be clear, the benefits of Windows Phone (and how well it syncs with everything else in the ecosystem) outweighs any cons from missing apps. But there are some apps (particularly niche ones) that I miss. Among these are my bank's, WebMD (medical diagnosis app), Google Docs Editor (for the occasional GDocs a friend puts on Google), Instagram, Draw with Friends (I missed not having this when the game was released and by the time this will come out on WP7, I think the fad will be completely dead).

What's Totally Broken:


Microsoft's ecosystem just sucks with music. Ideally, I'd like my music in the following places:

  • On my PC/laptop
  • On a portable music player (tiny enough to run with/work out at the gym with). If this PMP has support for something like Nike+ to track my workouts (either built in, or with an add-on), that's a big big plus.
  • On my XBox, so I can play through my home media center.
  • For many people, having their music on their phones would be nice. I don't care so much about this as the only time I listen to music on the go is when I'm running for which I need something much smaller than a phone (but that can still track my workout).
  • In the future: on my Windows 8 tablet. Now, I'll likely be getting a 64GB ARM tablet, and will probably not want ALL my music downloaded on to it as it'll take up too much space, so it would be nice if it could download a playlist from Skydrive when I want to play that playlist.

My current solution is so bad that it requires me to jump through hoops to keep music synced between iTunes, Windows Media Player,and the Zune player. Why?

  • The iPod nano is the only affordable portable mp3 player I know of with Nike+ (or similar technology) to track workouts. Forces the use of iTunes.
  • XBox can stream music from your computer, but only from Windows Media Player. You could use the Zune software on the XBox, but that doesn't allow use of your own music, only ones acquired through Zune.
  • Zune player is required if you want to sync something to your phone. You also need to do this ahead of time. Given most of my music has been aquired over years pre-Zune (and not from the Zune marketplace), I still can't just select a playlist that I didn't download and play it on the go.
  • To keep all this in sync, I've to manually run a little program called MusicBridge that syncs playlists from time to time.

So what would the ideal solution look like in my opinion?

  • The ideal solution would keep your music in the cloud/Skydrive. This would be synced to your laptop similar to how Skydrive syncs music and pictures. Additionally, similar to iTunes match, you should be able to add your own tracks that haven't been acquired from Microsoft's marketplace and they should end up in the cloud as well.
  • On the XBox, you should be able to select a playlist you edited on your PC and easily play it. This includes your own music as well, not just what's been acquired through Microsoft's marketplace. I'm not talking about streaming from your computer when it's on, I'm talking about streaming from the cloud (like iTunes match)
  • In the case of your phone, you should have the option of downloading a playlist on the go when you want to play it, as opposed to syncing your entire library or a playlist ahead of time.
  • Your portable media player should sync with the software on your PC and download your entire library. Now I know Microsoft won't make another Zune hardware anytime soon, so I'm hoping others like MotoActv (which has software to track workouts too!) will sync with this new solution.

I'm really hoping XBox Music that comes out sometime this year, will do all the above, and I can finally have all my devices just work together beautifully. I wonder what others' experiences have been who've tried out Microsoft's ecosystem? Have you had similar/different issues?