I also experience this problem on Ubuntu Xenial. The prompt is:

 ┌───────────────────────────────────────────────────────────┤ Configuring 
docker.io ├────────────────────────────────────────────────────────────┐  
  │                                                                             
                                                                   │  
  │ If Docker is upgraded without restarting the Docker daemon, Docker will 
often have trouble starting new containers, and in some cases even     │  
  │ maintaining the containers it is currently running. See 
https://launchpad.net/bugs/1658691 for an example of this breakage.             
       │  
  │                                                                             
                                                                   │  
  │ Normally, upgrading the package would simply restart the associated 
daemon(s). In the case of the Docker daemon, that would also imply         │  
  │ stopping all running containers (which will only be restarted if they're 
part of a "service", have an appropriate restart policy configured,   │  
  │ or have some other means of being restarted such as an external systemd 
unit).                                                                 │  
  │                                                                             
                                                                   │  
  │ Automatically restart Docker daemon?                                        
                                                                   │  
  │                                                                             
                                                                   │  
  │                                           <Yes>                             
                 <No>                                              │  
  │                                                                             
                                                                   │  
  
└────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────────┘
  

It's seems to be not configurable by dpkg --set-selections:

root@server# dpkg --get-selections docker.io
docker.io                                       install

I could upload a vagrant box to demonstrate this issue when running apt-
get upgrade -y. I try to automate the upgrade process, but this atm
blocks the upgrade and CI pipelines with interactive prompt. I'm also
trying to build a workaround wrapper with expect.

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https://bugs.launchpad.net/bugs/1798656

Title:
  gtk3 frontend gives no widget for answering a boolean prompt

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