package libssl1.1 1.1.1f-1ubuntu2 [modified: usr/share/doc/libssl1.1/NEWS.Debian.gz usr/share/doc/libssl1.1/changelog.Debian.gz] failed to install/upgrade: trying to overwrite shared '/usr/share/doc/libssl1.1/NEWS.Debian.gz', which is different from other instances of package libssl1.1:i386

[Jay de Halas]

Attempting to install legacy 32 bit version of libssl.so.1.0.0 to allow an old app to run.

ProblemType: Package
DistroRelease: Ubuntu 20.04
Package: libssl1.1 1.1.1f-1ubuntu2 [modified: usr/share/doc/libssl1.1/NEWS.Debian.gz usr/share/doc/libssl1.1/changelog.Debian.gz]
ProcVersionSignature: Ubuntu 5.4.0-37.41-generic 5.4.41
Uname: Linux 5.4.0-37-generic x86_64
NonfreeKernelModules: nvidia_modeset nvidia
ApportVersion: 2.20.11-0ubuntu27.2
AptOrdering:
 libssl1.1:i386: Install
 NULL: ConfigurePending
Architecture: amd64
CasperMD5CheckResult: skip
Date: Thu Jun 18 14:37:52 2020
DpkgTerminalLog:
 Preparing to unpack .../libssl1.1_1.1.1f-1ubuntu2_i386.deb ...
 Unpacking libssl1.1:i386 (1.1.1f-1ubuntu2) over (1.1.1-1ubuntu2.1~18.04.5) ...
 dpkg: error processing archive /var/cache/apt/archives/libssl1.1_1.1.1f-1ubuntu2_i386.deb (--unpack):
  trying to overwrite shared '/usr/share/doc/libssl1.1/NEWS.Debian.gz', which is different from other instances of package libssl1.1:i386
DuplicateSignature:
 package:libssl1.1:1.1.1f-1ubuntu2 [modified: usr/share/doc/libssl1.1/NEWS.Debian.gz usr/share/doc/libssl1.1/changelog.Debian.gz]
 Unpacking libssl1.1:i386 (1.1.1f-1ubuntu2) over (1.1.1-1ubuntu2.1~18.04.5) ...
 dpkg: error processing archive /var/cache/apt/archives/libssl1.1_1.1.1f-1ubuntu2_i386.deb (--unpack):
  trying to overwrite shared '/usr/share/doc/libssl1.1/NEWS.Debian.gz', which is different from other instances of package libssl1.1:i386
ErrorMessage: trying to overwrite shared '/usr/share/doc/libssl1.1/NEWS.Debian.gz', which is different from other instances of package libssl1.1:i386
InstallationDate: Installed on 2020-02-21 (118 days ago)
InstallationMedia: Ubuntu 19.10 "Eoan Ermine" - Release amd64 (20191017)
Python3Details: /usr/bin/python3.8, Python 3.8.2, python3-minimal, 3.8.2-0ubuntu2
PythonDetails: /usr/bin/python2.7, Python 2.7.18rc1, python-is-python2, 2.7.17-4
RelatedPackageVersions:
 dpkg 1.19.7ubuntu3
 apt 2.0.2ubuntu0.1
SourcePackage: openssl
Title: package libssl1.1 1.1.1f-1ubuntu2 [modified: usr/share/doc/libssl1.1/NEWS.Debian.gz usr/share/doc/libssl1.1/changelog.Debian.gz] failed to install/upgrade: trying to overwrite shared '/usr/share/doc/libssl1.1/NEWS.Debian.gz', which is different from other instances of package libssl1.1:i386
UpgradeStatus: Upgraded to focal on 2020-05-09 (40 days ago)

[Dimitri John Ledkov (xnox)]

a legacy app most likely will not be using libssl1.1 but the older libssl1.0.0 which is no longer provided in ubuntu.

you need to create a chroot or a VM, or manually enable old series to download old libssl1.0 which may still be available for i386.