For the duration of my time at my current employer, they've provided me with a company-owned cell phone (that was also permitted to be used as my personal device). A couple months back, I started looking for new employment opportunities. I accepted an offer with a different company. Separating from the company, I've had to return the device and begin my own cell phone plan privately.
I headed down to the Verizon store, and signed up for a new plan. After powering up my shiny new iPhone, I started going through my photos and contacts to verify that everything was there as expected (thanks iCloud!) I thought everything was there, until a few days later when I went to text a buddy of mine, but couldn't find his contact information in my phone.
After a little investigation, I discovered that any new contact I had added in the last two and a half years with my employer was sync'd with the corporate Exchange server, and not iCloud.
"New phone, who dis?"
Needless to say, I could have ported the contacts over individually, but didn't want to enter 150 contacts manually. Being the resourceful IT guy that I am, I found a way to automate the process.
Send Contacts as Business Card
Switch on over to the "Contacts" section in Outlook (in the bottom-right corner, the little icon of a person, third from the left). I'm including screenshots, but blurred contact names.
Highlight all of your contacts, select "Forward Contact" and then "As a Business Card".
From here, Outlook should compose a new email, having all of your contacts listed as attachments. Enter an e-mail address and send these off. Then, download all of the attachments to your local computer.
When I tried to do all of my contacts at once, Outlook kept crashing. I had to break them into separate batches.
Change vCard Version
If you attempt importing these to iCloud at the moment, you'll get an error message like the following:
The reason for this is because by default, Outlook exports business cards as a .vcf file, in version 2.1. iCloud only supports versions 3.0 and above.
Open all of the .vcf files in a text editor (I prefer VS Code). Do a mass find and replace in all files. Any reference of
VERSION:2.1 needs to be changed to
Import to iCloud
Log into the iCloud Web interface at iCloud.com. Select "Contacts". Then, drag all of your recently-modified .vcf files to the Contacts scroll list as seen here on the left.
That's it! Your contacts will then be imported to iCloud. Verify that your contacts are there, by checking your iDevice.
Hopefully this helps make your migration slightly easier.