I wouldn’t worry too much about an error in attempting the update, as it can either contact the server and verify their copy of your licenses and update/activate or not contact the server and fail to make any changes.
Not a fan of this approach by Steinberg, and I wish they’d make a less plasticky dongle as an option for those of us who take Cubarse out of the building occasionally 
Update on an earlier rant related to the Windows 10 update:
I reinstalled the Steinberg elicenser software. While it complains servers cannot be reached, at least the stuff already on my soft licenser and dongle works now.
Steinberg just posted a statement in the news section of their website:
License server outage (September 26, 2016)
Due to technical issues, our license server is currently unavailable. Product activations and other license transactions cannot be processed right now. We are working tirelessly to remedy the problem and apologize for any inconveniences caused. Of course, we’ll keep you informed.
I can finally install everything and doing maintenance. Everything works find now.
ETA on servers ?
Reviving a thread to ask a question in the same vein:
After activating, is it possible to use the software without internet access (i.e. on the road)?
Yes
Once you’ve put the license on a USB dongle it should be good to go across multiple systems. Just move it to the second machine (no need to ‘register’ again).
You can run the eLicenser software without internet access for things like moving keys to a different dongle. In short, you only ‘register’/activate’ the license ONE TIME. From then on, it lives on your USB-dongle, or in a special software-dongle.
The internet access is only necessary when you are ‘activating’ a new license for the first time, or to run some of the optional device maintenance steps (some of those will update information on servers so there is a record of the serial number for the dongle to match a given license…particularly if you’re moving keys around between multiple dongles, but things should still work even if such maintenance steps are skipped, or fail).
eLicenser software does need to be on all the machines you’ll use the dongle with, as it also installs drivers and such; but, internet access is only needed to ‘activate’ brand new licenses for the first time.
Sometimes various OS security updates might temporarily break things. I.E. When the Windows 10 Anniversary Update installed on my system, I had to reinstall the eLicenser app. I had to do the same thing for my iLok stuff, and I also had to reinstall quite a few of the drivers for various bits of hardware on my system. The Steinberg servers were down that day, but everything started working again after the reinstall (since the keys were already on my dongles). In this particular case, for whatever reasons, the Windows 10 update decided to null and void the majority of my system drivers (like the ones needed for apps to access my USB dongles). Reinstalling them got it all working again.
Sorry I should’ve been clear–how about when I’ve activated via the soft eLicenser that doesn’t require the dongle?
In that case it might depend on the product. Some Steinberg products can be moved between a soft licenser and a usb licenser one time. Once it’s on a USB dongle, you can move it to other dongles, but not back to a software licenser. You don’t need internet access to move a key like this in order to use the software, but it is recommended that at some point you do run the maintenance cycle which does need an internet connection so Steinberg gets a record of what key is on what dongle via ‘serial number’.
Some titles might allow you to move a key back and forth freely between a dongle and the software licenser. Again, this will work without internet access, but it’s a good idea to run eLicenser maintenance with internet access when you do get a chance.
Some might let you ‘deactivate’ a product that is on the software licenser (no dongle), and ‘reactivate’ it to the software licenser (no dongle) on a different machine. In this case you will definitely need an internet connection, and the servers must be up and running in order to move a key between machines.
Hi, just purchased and upgrade to Cubase 8.5 from 6. Spent the best of the evening trying to get the license registered and i keep getting as server cant be reached error.
I am using the USB-Linceser thing dongle.
Things I’ve tried :
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Installed the latest version of the ELicenser Control Center
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Disabled the Firewall
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No success
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Moved the USB dongle to a different computer
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Installed the latest version of the ELicenser Control Center
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No success
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Disabled the Firewall
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No success
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Tried a different Network
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No success
Installed Wire Shark to trace the packets : I A’m reaching the server and getting responses :
Here is the last message I get…
HTTP/1.1 200 OK
Server: Apache-Coyote/1.1
Content-Type: text/html
Content-Length: 548
Date: Fri, 11 Nov 2016 06:08:12 GMT
Thanks, Ronald.
It would probably make more sense to post the exact error message you get, rather than the cryptic xml output, which apparently translates to “error 101”
Anyway, it appears the elicenser server is working as of now.
Thanks for the reply. The message is what is posted in the ELicenser Control Center stating that the server may be down.
Though that the returned data may be useful…
Anyway, problem solved.
Interestingly enough, the problem when away minutes after I posted this question.
Must have been down.
Regards,
Ronald.
I’ll send you a bill. 
Today the server is down again. It can’t process any transaction:
Oops, an error occurred!
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Same problem here 
yep same here, cant authorise H6
Confirmed here. What bad timing. Same was happening after the Cubase 9 release.
Steve, I don’t suppose you (or any other mods) have any means of letting someone in Steinberg know about this? For us it’s just inconvenience, but surely this is likely to lose revenue for the company – someone reading about this, twice in a few weeks, is not going to be filled with confidence about the eLicenser. I can’t believe that these servers are not monitored, and that nobody is alerted to their failure!
[EDIT:] back online now …