Greetings Jeff,
Thanks for visiting the Apple Support Communities! It seems you're unable to send data using AirDrop between your Mac and iPhone.
Check the "Allow me to be discovered by" setting, as outlined in the following article: Use AirDrop on your Mac - Apple Support
Make sure that your devices meet these requirements:
- Both devices are within 30 feet (9 meters) of each other and have Wi-Fi and Bluetooth turned on.
- Each Mac was introduced in 2012 or later (excluding the 2012 Mac Pro) and is using OS X Yosemite or later. To find out, choose Apple menu > About This Mac.
- Each iPhone, iPad, or iPod touch is using iOS 7 or later, with Personal Hotspot turned off.
Make sure that your devices can receive AirDrop requests:
- Choose Go > AirDrop from the menu bar in the Finder, then check the ”Allow me to be discovered by” setting in the AirDrop window. iPhone, iPad, and iPod touch have a similar setting. If set to receive from Contacts Only, both devices must be signed in to iCloud, and the email address or phone number associated with the sender's Apple ID must be in the Contacts app of the receiving device.
- Choose Apple menu > System Preferences, then click Security & Privacy. Click the Firewall tab, then click the lock and enter your administrator password when prompted. Click Firewall Options, then deselect “Block all incoming connections.”"
Kind regards.