I started out doing computer support for the gas & electric utility where I lived. One of the things I did was automate the management of the remote dial-in machines, running ReachOut on Windows with 56k modems. As a result of that work, I moved into the group at HQ responsible for standardization and software vendor management, initially to build out remote access for the entire company using what I'd built for the region I'd been in. We were way ahead of our time on things like instant messaging, hardware & software standardization, and software distribution and we were pushing vendors on both hardware and various types of software.
One of the things we did was to move the company from Banyan VINES, a network operating system with its own email and calendar software, to NT and Exchange. That's when I started using Exchange to store my contacts and calendar. Even when I was contracting and didn't have an Exchange account anywhere, I used Outlook at home. I have contacts in Outlook today, I kid you not, that were first created in about 1995 and have been migrated among various Exchange servers and home copies of Outlook over the years.
I got my first smartphone, a Blackberry, around 6 years ago. I even got my company to pay for it. We were really a startup then, with maybe 20 employees, tops, and when I was upgrading my phone they decided not to pay for Blackberry enterprise service, so I got Just Another Flip Phone. A couple of months later there was some snafu having to do with my not checking email often enough. I couldn't get email on my JAFP, so they decided (not to say realized) that I should have a Blackberry and agreed to pay for both the service and the phone, since I sure wasn't shelling out for a new phone. They got off pretty easy- I talked AT&T into giving me the discounted price even though it had only been a couple of months since I got the last Razr.
A couple of Blackberries later, I switched to an iPhone 3GS and have been on iPhones ever since. Of course, with the smartphones I've always had a connection to the Exchange server at work, with all my contacts automatically synchronized. I never really had to think about it much, other than to bring them all home once in a while so they'd be in my home Outlook.
Friday afternoon, on my way home from my last day, I deleted the Exchange account on my iPhone that linked to my now former office. I'm certainly not saying I hadn't thought about this already - I uploaded a copy of my exported Outlook contacts to Google Drive not more than 2 hours before - but since I hadn't done anything about it, it was a surprise to get a text message from my brother a couple of minutes later, labeled only with his phone number!
It used to be I knew by heart every phone number I dialed more than a couple of times. I still remember the phone numbers of some of my junior high and high school friends' parents, even though I haven't called most of them in 20+ years. I don't think I've actually ever dialed my brother's cell phone number, so I only know approximately what it is.
So here's the other thing I did while procrastinating from packing the other night: figure out how to get all those contacts from an Outlook PST file in Google Drive back into my iPhone, using either iCloud or Gmail.
I had done a couple of searches and made some initial attempts at this over the last few days. As I said, I was well aware that this was coming. iCloud's contacts page seems to allow you to import a single contact vCard at a time. I have hundreds of contacts in Outlook. One at a time would be very unpleasant, especially since as far as I've been able to figure out so far, Outlook doesn't allow you to export vCard, only import.
I had seen something on the web about using iTunes to sync from Outlook to the phone and then switching to iCloud which should then sync the contacts to there. I didn't really want to get into this last night, but the VP of Ops and IT refused (not unreasonably, to be fair) to leave my email account active for a few days now that I'm no longer an employee. I did not propose, however, to spend 4 days in Utah visiting friends with LW without having those friends' contact information.
I suppose I could just have put their information in the phone directly, but that's not really the way I'm likely to go. I didn't even think of it, for that matter, until just now.
The IT guy suggested the Outlook to iCloud option, so that's what I decided to try. Here's how to migrate existing contacts out of a Microsoft Exchange server to iCloud in bulk, for an individual user, via Outlook. Something similar applies with Outlook Express as well.
Oh, I should mention that if you have iTunes set up and syncing to your iPhone from your work computer, you can skip some of these steps. Jump straight to the "Connect your iPhone" step, #5.
Step 1: Export the contacts from Outlook to a .pst file
Outlook makes this pretty painless. The hardest part is finding the right place to do it for your version of Outlook. In Outlook 2010, the way I found was to go to the File menu and pick Options, then select the Advanced pane and find the Export button.
This will bring up a screen where you can choose whether to import (yes, after clicking the export button) or export and what. Tell it you want to export to an Outlook data file (.pst), pick the Contacts folder, tell it to include sub-folders, give the file a name, et voila. Oh, make sure you save it somewhere you'll be able to find it. The default is like 16 levels deep, so I put it in the Downloads directory.
Step 2: Get your backup file home
In my case, this involved Google Drive, but email, Box, Dropbox, or a USB stick are all options. Pick the method of your choice, and it doesn't even have to be one I've mentioned!
Step 3: Import the contacts into Outlook
There are a couple of ways to do this, and it depends on what you want.
My preference would have been to import the contacts, using the aforementioned Export button, which would have given me the option to merge and update duplicates and left me with just the one set of contacts folders.
Unfortunately, I had a little trouble getting my home Outlook to recognize the .pst file. I wound up only being able to get it to open the file using the Open data file option and telling it the .pst was a 97-2002 Outlook file. At least it opened, but that forced a little more of step 4...
Step 4: Merge, clean-up and dedupe the contacts (optional)
In my case, I had to select all the contacts in each contact folder in the newly opened file and drag them over to the main contacts folder in Outlook. It asked me whether to create a birthday in the calendar. I don't really care about that in this case because I'm not planning to use that calendar, but it wouldn't copy them if I told it not to. Whatever.
Since I had to drag them in, there were more duplicates than there might have been otherwise, so I spent a little time going through and deleting duplicates, adjusting some and deleting a few that I really don't need anymore... e.g. contacts with no valid information or for people I don't really know anymore. I also did some other cleanup, such as making sure everyone was being displayed an sorted correctly.
Step 5: Connect your iPhone
This one's easy. Connect the iPhone and bring up iTunes, if it doesn't come up automatically. Update to the latest version if you want. I knew I'd been procrastinating long enough, so I didn't bother.
Step 6: Set the phone for local sync of contacts
I had the phone set up to sync contacts to the cloud, so when I went to the iTunes info page for my phone (more on that later), I didn't have the option to sync with outlook. Go to settings on the iPhone, find iCloud, and turn off contacts.
Step 7: Sync contacts from Outlook via iTunes
This is the first bit of real magic, as far as I'm concerned. It would've been nice if I could have uploaded the contact .pst file directly to my iCloud account, or even better, just told the phone to copy all my contacts from the server to the phone, but this is what does that.
Select your phone in the iTunes device list. Go to the Info page. Click the checkbox to tell it to sync contacts, and pick Outlook.
Wait for it to sync and then notice that your phone now has all your contacts! Hallelujah, we're making real progress!
Step 8: Set the iPhone back to iCloud contacts
Now, the final step, which makes it all worthwhile. Go back into settings on the phone and back to iCloud. Turn ON contact sync.
That's it. In a little while, if you log into iCloud from a web browser and go to contacts, there they will all be!
At this point, if I stop procrastinating and pack, I can fly to UT for a long weekend with my Lovely Wife and have both the contacts I'm likely to need AND all the others safely in my phone. Where they belong.
P.S. Incidentally, I wrote a lot of this post using Blogger for iPhone while en route to SLC, in airplane mode. I copied the text out to Notes, just to be safe, but Blogger is actually capable of working in disconnected mode. Bravo.
P.P.S. It took me a few days to finish this, since LW and I have been in UT. I'll update this further to add screenshots and maybe additional notes in a few days.