USB over ethernet CAT5 cable extender 'avrdude timeout error'

Hello,

I am trying to connect my arduino mega to my macbook via an ‘usb over ethernet adaptor’.
So I go out my usb port to the adapter, then through an cat5 ethernet cable and then back to usb into my arduino mega .
The adaptor was around 60 bucks and is good quality.
This works perfectly with my arduino uno. This means I can perfectly upload sketches on my uno with 15 meters between my pc and the arduino. I even tested it wit a cable from 30 meters and this also worked.

But when I try to upload a sketch on my arduino mega I’ll get the ‘avrdude: stk500v2.. : timeout’ error.
You can see the error in the picture below.
I know there are other threads handling this problem, but in none of them I found a solution. These were all people that completely couldn't upload sketches at all. I can upload sketches whitout the adaptor perfectly, so something in this adaptor is not working with the mega.

My specs:
Official arduino mega 2560 (bought 1 month ago)
Macbook pro 2015 10.12
Updated arduino IDE
Cat 5 cable 10m link to the shop where I bought the adaptor

Why do I want this?
I’m studying in a theatre school. For my final thesis I am making a show control system for theatre shows and interactive installations. This uses the software ‘Millumin’. It offers a function that lets your arduino auto program and lets you control servos, motors and sensors together with sound, light, video,..
For this I need a continious usb connection.
Because my laptop needs to be in the control room and the arduino on stage, I bought this usb over ethernet adaptor to use my arduino over 15 – 20 meters.
Specs from the adaptor say it works till 60 meters.

Thing I’ve tried:
Putting a usb extender with external power on the end of it, this had no effect.
Pressing the reset button while uploading a sketch, had no effect
Using a very short cat 5 cable, has no effect
In the IDE I tried changing boards and serial ports, had no effect

So my question is, what can cause this problem? As this works with my uno and not with my mega, what is different between these two?
Could it be a power problem?
The software Millumin that I am using in fact doesn’t matter. If I can upload sketches in the arduino the serial communication works and then it will also work with millumin.

As this works perfect with my uno I am convinced this has to work with my mega.
I really need my mega to have more digital outputs.
Who can help me? You could really save me thesis project.
I could give more information if needed.

Thanks in advance!

Does the loopback test work with the extender in place on the mega?

DrAzzy:
Does the loopback test work with the extender in place on the mega?

I've did the loopback test with no succes. (with the ethernet adapter attached)
It doesn't write back in the serial monitor.

I've done the same with my uno and it also doesn't write back but I am still able to upload sketches this way..

Any ideas?

Update to this:

I tested this without the ethernet adapter, with a usb cable (length 30cm).
I'v got the same timeout error!
I don't get this error with a short usb cable...

So it is not the ethernet adapter that causes the problem I guess.

Any ideas?

woutclarysse:
So it is not the ethernet adapter that causes the problem I guess.

...or the long USB cable and the Ethernet USB extender are both causing the same problem.