Okay- so I tested this. The short of it is I think this is an issue that needs to be addressed, but I don't believe it's an issue with plugins. I believe the issue is with TPing back to the main Ruby island from the Overworld limbo ones lands in when they die.

To Test: I went to Ruby island. I died on purpose. I was respawned in the holding area in the Overworld, as expected. Hollmane wasn't able to collect my items. I was presented with the expected ‘If you want, you have to /unlockdrops’ message. It seems the drops plugin is working as expected. 

The Rub: (this is closer to my experience and heart than I'd care to admit (Sorry again, Coral)) Full transparency- I had a huge issue with my last run and was quite upset that nothing was done about it in the moment. After the moment had passed, there was nothing to be done about it from the mods side. That’s why I looked into this specifically. Drops seemed to be an issue in my Ruby fight as well.

Here’s what I think is happening. I think players die and stand here:

https://drive.google.com/file/d/1XX5NDZP0d0a9YfZcZK1UtcjZOu-4NnFY/view?usp=sharing

I stand and wait. I am never TPed back to the island. What’s the intended behavior here? I don't see or pay attention to the other hologram that tells me how to get back myself. Why? Because I'm desperate to get back and get my stuff and have tunnel vision. Also, the larger and more central hologram says I'll TP back automatically, and includes the word “Please.” When I see “please” on Wildercraft, I tend to be massively over-patient. This could easily time out my despawn time on my gear.

FURTHER-

The second hologram was only just recently added, probably as a way to "help" deal with this? Here's from my recorded session on 8/7/2020:

https://drive.google.com/file/d/1pXvSnTh1z7MsCvHEnzIzPZG5bfy3SfH2/view?usp=sharing

The semi-helpful second hologram isn't even there. I had no idea how to get back in this fight and just sat in this dumb room for several minutes before I headed to Redwood and disconnected, frustrated.

As for the drops issue: I have never been automatically TPed back to the main island. My guess is that people TP to another server and TP back or disconnect and connect to get back. Both of these actions unlock drops for that player (which they often don't know), and the only reason they disconnected in the first place is because they died and couldn’t/didn't know how to get back.

This may be a user knowledge gap at this point, but there was zero guidance on how to handle getting back to the main island. The main hologram seems to imply it will be automatic, but it doesn't seem to be. The second one wasn't there until recently.

Summary: I think my issue, as well as so many others', is that the new Ruby Dragon is all completely foreign to the playerbase. When you have people trying it, wanting to have fun, and hitting up mods asking for a little bit of leeway and assistance because the learning curve is impossible when there's zero knowledge on how to deal with these most basic of issues, there's going to need to be more flexibility on the mods sides to allow for that. I lost a Ruby Dragon egg that I bought when the dragon was at 1/10th health because I thought, "This is going well enough, maybe we can run another!" only to be killed by an impossible to kill dragon and told it 'wasn't a bug.' Some slight bit of ownership from the staff for the issues presented as well as more case driven responses from the mods that are on at the time would greatly benefit the playerbase.

Conclusion: You all know this is a problem. If it weren't, you wouldn't have added the second hologram about how to get back. Yet when met with player complaint, we're told these "aren't bugs," and Ruby Dragon fights "carry risks." You can't have it both ways. Admit this was a problem that was handled poorly and change it, or leave it as is for people to abandon this awesome feature because they can't be helped when something goes sideways.