Ride upload issue while connected to WiFI and Bluetooth after updating to SW 3.50

I was having the issue too. Once I forced a couple uploads via the edge unit, it just started working again. First time I had to push upload twice, next ride still no BT upload. Then I did a manual upload again and it worked - and my rides have synced correctly every time since (for a couple weeks). Maybe the workaround can work for some of you as well. 

I am also having problems uploading a ride.  I am using an iphone xs - ios 12.3.1, connect 4.20.0.14, edge 530 3.50.  I have been having upload problems since I upgraded to 3.50.  Previously, I had no issue uploading.  I usually have to try multiple times before the data uploads to connect.  This happens after every ride, since upgrading firmware.  I try uploading multiple times, and usually end up rebooting the 530, and disconnecting and reconnecting blutooth.  Before my last ride I deleted the 530 from the connect app, and reinstalled the device to the app.  This did not fix the problem.  I did notice after the last ride only one for the 530 blutooth connections was connected to the phone.  After restarting the app, both connections were present and I was able to download the ride, but the edge said the download failed, even though connect received the data.  I have not figured out any pattern to get the data to upload.  It seems to randomly upload after many attempts.

Hi Matthew, wanted to give you my experience:

I actually updated to 3.50 then reset the device to factory settings, deleted it from GC, and started the setup process over as if it were now out of the box, but with version 3.50.

Tested a few :10 'dummy' rides and they uploaded immediately via GC connected to my iPhone 7. Alright!

A week later, though, auto uploads are no longer working. I have WiFi turned off on the Garmin and iPhone settings show two Bluetooth data connections, GC runs and shows completed sync, but the ride doesn't show. 

The only consistent way I've found to make it work is turning the Garmin fully off/on and closing the GC app/reopening does the ride upload...

...or plugging it into my computer and letting Garmin Express handle the upload, but those days should be behind me.

Not good. I should mention the Edge 520 I replaced did not have this issue; uploads happened immediately after every ride. 

Thanks for the report.  In my case I only needed to bring GC from the background to the foreground and then the Edge will connect via BT and then upload the ride.  Until Garmin provides a fix you can try this (without having to turn off/on the Edge).  As previously mentioned I also didn't have a BT connection issue with the phone on my 520.  So I hope Garmin will take notice and fix this bug.

Yes I'm having exactly the same issue on my 530 and had no such problems on my 520 with the same phone. Really frustrating.

Edge 530. Software Version 3.50. iPhone Xs. Bluetooth still does not work / sync any rides and routes from GC as well. Annoying. Any ideas when Garmin will solve this issue?

I've been having this problem from day one with the 530. It's still continuing after 3.50 update after repairing. Am on Android. Bluetooth doesn't hold connection unless phone is unlocked with Garmin Connect open. When it comes to actual riding the Bluetooth stays disconnected for the whole ride, then when I get home, the 530 connects to the Wifi but doesn't automatically sync the rides. The phone doesn't sync the rides either until you start Garmin Connect again, then it works through the app and Bluetooth. Even trying to force the upload via the wifi doesn't work.

Same here. No BT connection when the app is not active on Android. When the 530 is connected to GC the sync is not working. I need to connect the 530 with the USB cable to my pc for the syncing to work.

I am having the exact same issues.  I have done these steps at least 15 times (though the problems got worse AFTER the update to 3.5).

1.  Reboot Edge 530

2. "Forget" Edge from iOS BT settings menu.

3. Add device in Garmin Connect

4. Turn on pairing mode on the Edge.

5. Found device, match the PIN number, approve adding device via BT.

6. GC - "Sorry your Device was not found"

One in 15 times, I've gotten the device to be recognized. In these cases, I've tried to sync - 'device busy errors'.  I've tried configuring Apps/Widgets - 'unable to connect to device'.  All the while, the phone says the device is connected and GC sees the device as connected.

I've also attempted to update Edge to Beta 3.55.  Exact same issues.