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Previously (before iOS 13) I was able to attempt to begin a WiFi sync from my phone by going to Settings > General > Wifi Sync

I no longer see that option. On my computer (currently on macOS 10.15) I'm at the mercy of the phone showing up in the Finder (just as I used to be at the mercy of it showing up in iTunes) whenever that strikes the phone or the computer's fancy (I'm unable to determine what makes it appear or not.)

Is there a way to tell the phone to begin a sync? (or alternatively tell Finder to look and show me the phone which is connected to the same WiFi network and ready to go if it would just show up ok Finder)

  • Does your wifi allow such visibility? I have a faint memory of a discussion where router was not configured to allow network discovery. – ankii Oct 14 at 9:18
  • Yep it has connected and synced. The phone just seems to show up (or not show up) at random. – dwightk Oct 14 at 10:58
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After iOS 13 and Mac OS Catalina, it seems that Apple needs to introduce a helper utility to pair the device.

I’m an iOS developer and we use Xcode’s built in utility to pair and unpair devices.

Sometimes the device doesn’t get automatically connected so we have to connect it via a fixed IP address.

Open Xcode (can be downloaded free)
Open devices and simulators
Connect via IP

More details can be found here.

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Ankii mentions this Apple Support article which states:

When the computer and the device are on the same Wi-Fi network, the device appears in iTunes. The device syncs automatically whenever plugged in to power and iTunes is open on the computer.

  • iTunes is no longer a part of macOS as of 10.15 – dwightk Oct 14 at 9:02
  • That is basically how it works now but with Finder instead of iTunes. I’m looking for a way to move things along when both devices ARE on the same WiFi and the phone isn’t showing up in Finder. – dwightk Oct 14 at 9:07
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Source.

Following these steps work for me. The Apple page was referenced in an earlier answer however the steps to enable it were not mentioned.

Sync your content using Wi-Fi

After you set up syncing with the Finder using USB, you can set up the Finder to sync to your device with Wi-Fi instead of USB.

  1. Connect your device to your computer with a USB cable, then open a Finder window and select your device.
  2. Select “Show this [device] when on Wi-Fi" and "Automatically sync when this iPhone is connected".

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  1. Click Apply.

When the computer and the device are on the same Wi-Fi network, the device appears in the Finder. The device syncs automatically whenever it's plugged in to power.

  • as I understand OP has done such sync first, but it is unreliable. It doesn't work when they want it to and they want to force sync or force rescan the network for the device. – ankii Oct 17 at 3:58
  • OP didn't mention if the followed the initial setup so I wanted to be sure. From my research, the iPhone will not sync if there's nothing to sync since the last connection. I'm not able to find a way to force a sync at this time. – fsb Oct 17 at 12:16
  • ah yes.. I too had to interpret from comments. Some workarounds to do a rescan are similar to turn off wifi on both and turn back on. Idk who can guarantee for that. – ankii Oct 17 at 12:17
  • Thanks, I did the initial pairing via USB... It looks like it is doing an alright job of automatically syncing over WiFi... I would just like to be able to reliably push a button on my computer (or phone) to do a sync now (e.g. if I'm about to go on a road trip and want my playlists updated.) – dwightk Oct 19 at 3:17
  • I don't think that's possible. I didn't find any info regarding a manual or on-demand wifi sync. – fsb Oct 19 at 3:52

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