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I doubt that will work. Garmin really only allows transfer via Bluetooth to Garmin apps. They allow importing via the FIT files into other sources, such as SSI app, Subsurface, etc.
FYI: Garmin will let you upload FIT files directly into Garmin Connect on your computer. This will automatically populate the Garmin Dive app on your phone. Navigate to "connect.garmin.com." Log in. Click on the cloud with the arrow running through the middle located in the upper right hand corner of the screen. Click "import data." From there you can manually import "Garmin Activity Files (.tcx, .fit or .gpx format); Fitbit® body or activity data (.xls, .xlsx or .csv format)." (Quoted from Garmin Connect's upload screen.) You must find the files on your computer (or on a device connected thereto including your Descent) and enter the path for upload. It's a pain. It is possible that activities, including dives, recorded on devices that save in one of the formats listed above can also be imported, but I haven't tried.
 
Try force quitting Garmin Connect. Maybe it is doing the grabbing. Also try quitting android access apps e.g. Android File Transfer if they are running.
I believe I did, but can't hurt to try again. No Android File Transfer or anything on the Mac.
FYI: Garmin will let you upload FIT files directly into Garmin Connect on your computer. This will automatically populate the Garmin Dive app on your phone. Navigate to "connect.garmin.com." Log in. Click on the cloud with the arrow running through the middle located in the upper right hand corner of the screen. Click "import data." From there you can manually import "Garmin Activity Files (.tcx, .fit or .gpx format); Fitbit® body or activity data (.xls, .xlsx or .csv format)." (Quoted from Garmin Connect's upload screen.) You must find the files on your computer (or on a device connected thereto including your Descent) and enter the path for upload. It's a pain. It is possible that activities, including dives, recorded on devices that save in one of the formats listed above can also be imported, but I haven't tried.
Hmm. This sounds backwards from the way I'm currently doing it. Without doing anything, the dives are synced to my phone as soon as it's in range. It shows up in Garmin Dive and Garmin Connect on my phone. I add some details to Garmin Dive. Then at home, just open Garmin Express, then go to connect.garmin.com and dive activity is there. For importing to Subsurface and/or SSI log, I just download the .FIT from connect.garmin.com and it's saved to the folder that Subsurface and SSI can import from.

I guess the download from dive computer to computer and into connect.garmin.com would work if I didn't have my phone.
 
Hmm. This sounds backwards from the way I'm currently doing it. Without doing anything, the dives are synced to my phone as soon as it's in range. It shows up in Garmin Dive and Garmin Connect on my phone. I add some details to Garmin Dive. Then at home, just open Garmin Express, then go to connect.garmin.com and dive activity is there.
Yup. For me that's how it works 99.X% of the time. Occasionally Garmin has a problem (thankfully for me it has never occurred when syncing a dive but a handful of bike rides and runs haven't initially synced properly). I have a theory on why but it's a long story that I won't burden you with. One work around when that happens is the manual route I described. It's an option I think you may benefit from knowing about just in case a dive doesn't sync right some day. I hope you never have to use it because compared to the automatic upload it's a pain in the rear.

Edit: if you just happen to be without your phone, rather than experiencing the sync error, Garmin Express will automatically upload dives to Connect when you plug in to your computer.
 
https://www.shearwater.com/products/teric/

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