Hello squill,
Welcome to Apple Support Communities. It sounds like you're having trouble syncing your contacts to your iPhone. I'd be happy to provide information that may help you troubleshoot this.
- First, back up your iPhone and Outlook data.
2. Make sure the iOS version on your iPhone is up to date.
3. Apply all Windows updates.
4. Check Outlook compatibility:
- Microsoft Outlook 2007, 2010, 2013, or 2016. Check the version of Outlook.
- Outlook must be locally installed, not Click-to-Run. If you use Click-to-Run, switch to a local installation.
- Outlook data must also be stored locally on your computer and in an unencrypted Unicode PST file.
5. Reset iTunes sync history
- Open iTunes.
- From the menu bar at the top of the iTunes window, choose Edit > Preferences.
- Select the Devices tab.
- Click the Reset Sync History button.
- Try to sync again.
I hope that helps. Take care.