Sync problems: Training calendar runs don't show up, workouts don't sync at all

Hi,
I have a similar issue on my Edge 1000: for given training plan, some of scheduled workouts did sync to a device, and others did not. The only workaround is to go to (in garmin connect)Training -> Training plans -> find your scheduled plan -> find your excercise (which did not synced with device) -> edit -> and then send to the device (i.e. using garmin express app). Technicaly it works, but it is very anoying.
However, I was wondering, why some of workouts synced, and some of them did not, and then I figured out, that problem appears, when names of particular workouts in the plan are not unique. Lets say: I have training plan named "Time Trial Phase 1: Base", and it contains workouts named as: 5 Min. Tempo, Fitness Test(10 Min.), Zone 2 Aerobic, Fitness Test (3 Min. + 20 Min.), 5 Min. Threshold Intervals (3 Times), Zone 2 Aerobic, Zone 2 Aerobic, 5 Min. Threshold Intervals (5 Times), and so on. In the callendar on garmin connect (web and mobile) all the workouts are properly scheduled, but at the device only one workout for given workout name is visible.
So I tried to make unique names for workouts with repeating names. The most frequent workout name in the plan was "Zone 2 Aerobic", so I have edited names for a few of them by adding scheduled date (month, day) to workout name (I got "1201 Zone 2 Aerobic", "1202 Zone 2 Aerobic", and so on). Then I've made a standard sync for the device, and voila! - workouts which was previously missing just appeared on the device.
That is why I suspect, that training plans sync problem is related to non unique names of particular workouts - maybe the app just "see", that there is already a workout with this name on the device, and just skips syncing?
The simplest workaround (for programmers :)) would be adding a scheduled workout date to the name of the workout in callendar during operation of scheduling particular training plan (i.e. workout scheduled at 29-11-2019 would be named "20191129 Zone 2 Aerobic" instead of just "Zone 2 Aerobic").
Of course much more elegant solution for syncing should be based on checking existence of some internal identifiers of training plan + workout + scheduled date (or however else these data are organised) instead of using just a workout name to identify it.

I have the same problem in my new vivoactive 4. Terrible experience as a new Garmin customer

I have been mailing with garmin support for weeks (garmin reply takes a full week...) without any result. They keep asking me the wrong questions. I repeatedly tell them, that Garmin Express has no more "send to device" button! Or, at Garmin they don't have a clue of what they are doing, or, it's just a trick to get customers with "older" devices (my FR235 is 3 years old) to buy a new one! This is very irritating! Within a month or 2 I start my marathon schedule (1 of the Garmin schedules - that is very good BTW) but I can't send it to my Forerunner anymore (last year and the year before this worked without any problem). Very frustrating... Mmm... just got a nice brochure from Polar... 

It's embarrassing because they know this is a problem. And they've known it for more than a year. And they have been making other changes to Garmin Connect in terms of the app and the web experience. How can this feature be such a low priority that they are spending time on other enhancements rather than fixing this one?

This may be the case but I think it's different from what others here are experiencing. In my experience, the entire "send to device" functionality disappears from time to time. It's not a matter of a couple workouts not transferring but being able to transfer a training plan at all.

 Can’t agree more.  They are supposed to be a leader in this type of tech and they can’t even get a year + synch issue corrected?  I’ve never considered Polar before, but Garmin either doesn’t care, or is too inept to fix.  I’m a month into trying to get them to fix and “work arounds” are all they offer

It's unbelievable.... A company this big as Garmin, that is not capable of fixing one of the main features - the core feature - of their devices... My 235 was for 3 years my true training buddy. We spend hours and hours training and running. The Garmin schedule worked even perfectly for me. I don't know what's with this people...

... just got here today a nice Polar brochure... :-)  Real cool stuff they have...

I've given up trying to use the PC Garmin Connect website to download my workouts to my FR230.  I sync exclusively with the phone app now and that automatically downloads workouts.