Public bug reported:

Checking package manager
Reading package lists... Done    
Building dependency tree          
Reading state information... Done

Calculating the changes

Calculating the changes

Could not calculate the upgrade

An unresolvable problem occurred while calculating the upgrade.

If none of this applies, then please report this bug using the 
command 'ubuntu-bug ubuntu-release-upgrader-core' in a terminal. If 
you want to investigate this yourself the log files in 
'/var/log/dist-upgrade' will contain details about the upgrade. 
Specifically, look at 'main.log' and 'apt.log'. 


Restoring original system state

Aborting
Reading package lists... Done    
Building dependency tree          
Reading state information... Done
=== Command detached from window (Thu Oct 15 10:18:11 2020) ===
=== Command terminated with exit status 1 (Thu Oct 15 10:18:21 2020) ===

At this point it stalls

ProblemType: Bug
DistroRelease: Ubuntu 18.04
Package: ubuntu-release-upgrader-core 1:18.04.38 [origin: unknown]
ProcVersionSignature: Ubuntu 4.15.0-118.119-generic 4.15.18
Uname: Linux 4.15.0-118-generic x86_64
ApportVersion: 2.20.9-0ubuntu7.17
Architecture: amd64
CrashDB: ubuntu
CurrentDesktop: Unity:Unity7:ubuntu
Date: Thu Oct 15 10:05:16 2020
InstallationDate: Installed on 2015-03-02 (2053 days ago)
InstallationMedia: Ubuntu 14.04.2 LTS "Trusty Tahr" - Release amd64 (20150218.1)
PackageArchitecture: all
SourcePackage: ubuntu-release-upgrader
UpgradeStatus: Upgraded to bionic on 2020-10-15 (0 days ago)

** Affects: ubuntu-release-upgrader (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug bionic dist-upgrade third-party-packages

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https://bugs.launchpad.net/bugs/1899856

Title:
  Upgrade attempt fails

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