When I first set up the Windows Phone 7 device, I added my Facebook and Windows Live account credentials. The information from those two services has populated my People Hub with a variety of contacts, but it is not as current, accurate, or comprehensive as the information I maintain in my Outlook Contacts on my local PC. So, today's 30 Days With Windows Phone 7 post is dedicated to getting my Outlook Contact data synced up with Windows Phone 7.

If you rely primarily on Windows Live for maintaining your contacts, or you use Exchange or Office365 for your Outlook mail, then you are all set to just start using Windows Phone 7 right out of the box. However, if you maintain your contact data somewhere else--including locally on your PC in Microsoft Outlook--you're going to have to figure out how to sync it up with Windows Live in order to pull that information into the People Hub.

For Outlook, the simplest solution seemed to be to use the Outlook Hotmail Connector to get my local Outlook data in sync with my Windows Live account. Or...not so much. You might notice that this is Day 12 being posted on the morning of Day 13. Yeah, that's how simple it was, at least for me.

I did a Web search and found a Microsoft Support page titled Sync Your Outlook Contact to Windows Phone. That sounds about right, so I decided to follow along.

Step 1 is to check what kind of email account you are using if you don't already know. Basically, this step determines if you are using Exchange or not. My accounts are set up in Outlook as POP/SMTP, so I moved on to Step 2. The next step just walks through adding the email account to the Windows Phone 7 smartphone, and I have already done that, so I skipped on to Step 3.

Step 3 is called "Sync Your Contacts", so now I feel like I am finally getting somewhere. There are two solutions available: use the Outlook Hotmail Connector, or sync manually. The support page recommends using the Outlook Hotmail Connector. I know that when I first used a Windows Phone 7 device last year I used the Outlook Hotmail Connector and it seemed to work just fine, so I decide to go with that.

The step includes a link to the Microsoft Outlook Hotmail Connector overview page which includes links to download either the 32-bit or 64-bit version of the Outlook Hotmail Connector. There are also some instructions to figure out which version of Outlook you are running. I am using the 32-bit, so I download the appropriate client.

Step 3 of Step 3 simply says, "Install Outlook Hotmail Connector," so I did that. Then, Step 4 directs me to move on to the next section to copy my contacts to Windows Live. That section explains, "Once you have the Connector installed, follow the directions below according to the version of Outlook you're using." The problem is that the "links" under Outlook 2010 and Outlook 2007 aren't linked. It says, "Click here to show/hide solution", but the solution is elusive because it is just text with no link.

I thought maybe it would "just work" so I waited...and waited...and waited. I kept checking my Windows Live contacts and the contacts on my Windows Phone 7 to see if new info from my Outlook Contacts was getting synced up. Nothing.

Finally, I started doing some additional Web searches to try and troubleshoot. I rebooted. I did a Repair install of the Outlook Hotmail Connector. I rebooted. I uninstalled the Outlook Hotmail Connector. I rebooted. I re-installed the Outlook Hotmail Connector. I rebooted.

The main problem I have is that there is no indication at all that it is working or not. I don't see any evidence of the Outlook Hotmail Connector being installed anywhere. There are no additional folders or entries in Outlook that I can find. There is nothing in the Systray in Windows. Yet, I am also not getting any error messages or any indication that there is anything wrong.

I tried doing some more online research and troubleshooting. I found an entry on the Outlook Blog titled "New Outlook Hotmail Connector released" and clicked it. There is a step in there describing how to verify what version of the Outlook Hotmail Connector is running. It told me to click File, then click the Additional Information button. One problem. I don't have any button called Additional Information available under File.

Eventually I noticed that many of the examples I was stumbling across on the Web had the Hotmail account set up in Outlook as a separate account. I didn't really want to clutter up my Outlook with additional folders I don't plan to use, but I decided to give it a shot.

Finally, it seemed like I made some progress. My Hotmail email account was now accessible as its own folder. When I click on Contacts in Outlook, I can see a new folder of contacts from my Windows Live account. I even had a little message at the bottom of Outlook letting me know that it is connected to Windows Live Hotmail.

I still don't see any syncing going on, though. Finally I decided to simply manually copy the contacts from my main Outlook Contacts to my new Windows Live contacts folder. There are of course duplicates, so I got an alert asking me how to handle those. I directed Outlook to merge the information using my Outlook data as the primary.

Next, as the data was being copied I got alert, after alert, after alert declaring, "The company name exceeds the limit of 40 characters. Type fewer characters before you click OK or excess letters will be automatically removed." The only problem is that it doesn't provide me with any indication which contact is in question, or any means of altering it. I can choose between blindly clicking "OK", or clicking "Cancel", hoping I can figure out which contact is the problem, then starting the copying process over again. I just click OK.

As it finished copying, I got a message stating, "Cannot copy the items. Some items cannot be copied. They were either moved, or deleted, or access was denied." Um, OK. Which contacts? I didn't move or delete anthing mid-copy process, and I should be the only one with access or authority to deny access, so I don't understand what the problem is.

At the bottom is a taunting link asking, "Was this information helpful?". No, Microsoft. No, it was not helpful at all.

It was an arduous and frustrating journey, but my Outlook contacts data is now incorporated with my Windows Live contacts data so it can be synced with my Windows Phone 7 device. As far as I can tell, though, there is no automatic syncing going on. If I add or change a contact in Outlook, I am going to have to manually copy it over, or make the same add or change in the Windows Live contacts in order for that information to get to my phone.

I am sure my experience is not the norm. I did this before and it wasn't this hard. I still thought it was a convoluted pain in the ass, but it wasn't so frustrating just to get it set up in the first place.

That said, Microsoft really needs to automate this entire process. Part of the initial setup of a Windows Phone 7 smartphone should include an automatic query, or asking the user if they use Outlook for contacts and calendar data. If so, Windows Phone 7 should automatically install the Outlook Hotmail Connector or whatever tool is required, and automatically pull that data to Windows Live so it can be propagated to the Windows Phone 7 device.

The information should be able to be synced in the background without cluttering up Outlook with folders from Hotmail. And, most importantly, it should automatically sync all changes made to Outlook. I shouldn't have to be involved in setting up or babysitting the contact info--especially when I am using Microsoft Outlook in the first place.

My iPhone syncs my contacts and calendar from Microsoft Outlook just fine, and doesn't require Tylenol or anger management.

Read the last "30 Days" series: 30 Days With Google+

Day 11: Following in the (Wrong) Footsteps of iOS