Another Local Files Issue

[PathfinderRyder]

Plan

Premium

Country

Canada

Device

iPhone 11 Pro Max, Galaxy S10+, iPhone XR, Windows 10 Laptop (X1 Yoga), MacBook Pro 13" 2018, Custom Built Windows 10 Desktop

Operating System

iOS 13.7, Windows 10 1903, MacOS Catalina 10.15.5, Android 10 

My Question or Issue

The dreaded "I can't sync my local files with my phone". I got a replacement 11 Pro Max through AppleCare+ and I had to re-download my songs. It used to work fine in the past with a Windows device (with the firewall turned off) and my iPhone. However, it didn't work and here are the things I tried.

Scenario 1:

11 Pro Max --> Home Wifi  <-- Windows Laptop with firewall turned off

Scenario 2:

11 Pro Max --> Home Wifi <-- MacBook Pro with firewall turned off

Scenario 3:

11 Pro Max --> Home Wifi <-- Desktop with firewall turned off (And connected via ethernet)

Scenario 4:

11 Pro Max --> XR with Personal Hotspot <-- Windows Laptop with firewall turned off

Scenario 5: 

11 Pro Max --> XR with Personal Hotspot <-- MacBook Pro (you know the drill by now, with firewall turned off)

Scenario 6:
11 Pro Max with Personal Hotspot --> Windows Laptop

Scenario 7:
11 Pro Max with Personal Hotspot --> MacBook Pro

Scenario 8:

11 Pro Max --> S10+ hotspot <-- Windows Laptop

Scenario 7

11 Pro Max --> S10+ hotspot <-- MacBook

I tried literally everything with all different devices and networks. I made 2 new playlists with the local files I want to sync but it's just not working. I have "show unplayable songs" enabled and when I play the local file with another device, the 11 Pro Max knows what song is playing as it highlights the currently playing song in green. But it just won't sync for some reason. 

I honestly don't know what else I can do. Any answers are appreciated!

[PathfinderRyder · Accepted solution]

Solved it. Turns out I got "Enable sync from desktop" disabled under the Local Files option in the Settings menu.