Is a phone payment (as in the iPhone Upgrade plan through Apple/Citizens One) considered a communication expense or an asset? I am not asking about my Verizon bill.

Cell phone plan upgrade will be considered an expense.  Cell phone purchase may be added as an asset, if it qualifies for the new business safe harbor election, it may be written off as an expense.  To learn more please see cell phone business expenses.  To enter this business expense, please see the steps in the TurboTax FAQ below.

https://ttlc.intuit.com/replies/5802554

Can you please clarify? The iPhone Upgrade plan is essentially a lease program for the device itself.

Basically, anything you pay for the phone that is used for business is a business expense.  Therefore, you can include the monthly payment for the year as a business expense on your taxes.