Can't Send Workouts to Device from Garmin Connect (for weeks)

Try clearing workouts from your device.
Try sending fewer workouts in one hit.

I decided to try and build some workouts the other week. these loaded to my watch without issue. i do note that i did do it slightly differently.
i created the workout in GC web. after a while i checked to see if these appeared in the GCM app. In app More then workouts.
all the workouts were created and appeared in app. i could select each one on the arrow to the side that allowed me to review and ensure i have the correct workouts loaded(or perhaps appearing would be a better term as i am sure this is just a UI to the web). once i was happy in the top corner i had the option to send to device (just that workout).
i thn check my watch and it was synced via bluetooth.
i followed the same for the remaining workouts i created.
i know this might be the cautious approach but i was trying to understand how this all meshed together if i wanted to make some changes etc and did not have a PC handy (you can edit workouts on the app too.

i agree that it should be ok from PC and garmin express but this way worked for me so may help you trouble shoot

I was able to send yesterday's workout to my watch via my phone, but since it's from a Garmin workout plan I don't want to be stuck with this method, cause I'll have to send each day's workout and then delete them eventually to ensure space exists for new ones. The scheduled workout functionality should not need to be worked around, that's my peeve. It should work, and be fixed in less than two weeks if it breaks. I'm waiting on a response from Garmin via support email. I imagine others aren't having this issue or there'd be a bigger thread on it? Or do few people use the scheduled workouts feature? I live by it!

Oh Ok i misunderstood the original post
I thought you were creating generic type workouts ( ie building a workout to follow like WU 10 X1km repeats CD) that you would repetitively use rather than scheduled workouts.
I have seen other threads on this in the past (and some of them may have been training plans) but they still end up scheduled in your calendar as workouts to use.
In these threads it seemed that you needed to send 1 work out then after that you could send all workouts in your schedule (ie mass transfer using GE).
I may be further miss interpreting what you are doing here but this is some of the info I have seen in reading these forums over time

I see no option to send just one using my computer and Garmin Connect with the watch connected directly to computer with USB (the workout I've been using is to send just the workout on my schedule for that day using my phone and bluetooth connection to the watch). With GC and USB to watch, it's all or nothing for sending my schedule over.

It's never been an issue in the past, but now I get an error as soon as I hit send and it just won't go. It's been two days with no response from Garmin yet.

I'm having similar problems. .I had two custom workouts on my watch, and after the last software update, they disappeared. I've tried to send to them to the watch again, but when sync completes, they're not there. I've deleted the workouts, created them again from scratch... it doesn't matter what I try to do, the custom workouts do not ever get to the watch.

I found where to send just one workout from Garmin Connect via USB and it worked just fine.

I baffled the email support guy so they directed me to the phone support guy. We tried a ton of stuff before he resorted to having me delete workouts from my calendar. I deleted a little under half of them and was able to sync again. I added back five of them and wasn't able to sync again. I removed a couple and was able to sync again. Eventually, I got myself back to where I was with my calendar and also able to sync. It seemed like it was just glitching on one of the workouts on my schedule. I guess I tracked it down, though it still isn't clear to me which one it was.

Bump. Has there been any news on this? Still not working.

I'm also have this same issue for both my Forerunner 230 and Forerunner 235. I have deleted all prior training plans and workouts from both devices. I cannot get the training programs to load via PC and USB cable, nor Garmin Connect app on my phone (Samsung Galaxy 9+). Is Garmin still working on this issue?