Transferring files over bluetooth is slow. I have a TicWatch smartwatch and I wanted to transfer files to the watch over WiFi. There are a few apps available on the Play store but I think doing this over adb is secure as this happens on your local network and doesn’t use a third party tool.
Though I have only tested this on Ticwatch Pro 3, this guide should work for all Wear OS smartwatches.
You will need to do some setup on the watch first and then connect using the ADB command line tool.
On Watch
Go To Settings > System > About
Tap Build number multiple times until Developer Mode is enabled
Come back out to System Menu
Last menu item will be Developer options.
Tap and enable ADB Debugging
Tap and enable Debugging over WiFi. Also check the port. It should be 5555.
Once WiFi debugging is enabled, you need to find out the IP address.
This can do this with the Watch’s MAC address.
Go to Settings > System > About and Tap on Watch name. This should show the MAC address.
You should be able to use the MAC address and look it up on connected devices on your router’s connected devices view. You could use arp command as well.
Once you have the IP address, you can use it to connect to the watch over WiFi with adb tool.
On Terminal
$ adb connect your.watch.ip.address:5555
You may be asked for giving permission to allow debugging on your watch.
You can show connected devices over adb with
$ adb devices
To copy/push something to your watch, you would need to know where you want to put the file. /sdcard is usually where you do this.
$ adb push /path/to/local/file /sdcard/some_existing_folder
Do adb pull to get files from the watch.
You can also list files with adb shell command
$ adb shell ls -R /sdcard/some_existing_folder
Pushing files over WiFi should be significantly faster than bluetooth so I hope this post helps you save some time transfering files to/from your smartwatch.
Until next time .. happy pushing!!!
{ problem: 'solved' } 
you’re the boss!!! everything failed except your solution. My new TicWatch 3 is usable now. Almost one day I lost with apps which want a money for full copying via bluetooth. Here I can copy full local directories into watch. Under windows the command is i.e.: D:\platform-tools\adb.exe shell ls -R /sdcard ( not $ adb “command”) ” D:\platform-tools\ adb.exe ” folder where “You” put adb drivers