Public bug reported:

$ sudo debootstrap trusty rootfs-trusty http://ftp.byfly.by/ubuntu
I: Retrieving Release
I: Retrieving Release.gpg
I: Checking Release signature
I: Valid Release signature (key id 790BC7277767219C42C86F933B4FE6ACC0B21F32)
I: Retrieving Packages
I: Validating Packages
I: Resolving dependencies of required packages...
I: Resolving dependencies of base packages...
I: Checking component main on http://ftp.byfly.by/ubuntu...
I: Retrieving adduser 3.113+nmu3ubuntu3

...

I: Configuring ubuntu-minimal...
I: Configuring libc-bin...
I: Configuring initramfs-tools...
I: Base system installed successfully.

Now add trusty-updates to sources.list:

$ cat rootfs-trusty/etc/apt/sources.list
deb http://ftp.byfly.by/ubuntu trusty main
deb http://ftp.byfly.by/ubuntu trusty-updates main

Update & upgrade:

$ sudo chroot rootfs-trusty apt-get update
Ign http://ftp.byfly.by trusty InRelease
Get:1 http://ftp.byfly.by trusty-updates InRelease [65.9 kB]
Hit http://ftp.byfly.by trusty Release.gpg
Hit http://ftp.byfly.by trusty Release
Get:2 http://ftp.byfly.by trusty-updates/main i386 Packages [718 kB]
Get:3 http://ftp.byfly.by trusty-updates/main Translation-en [376 kB]
Hit http://ftp.byfly.by trusty/main i386 Packages
Get:4 http://ftp.byfly.by trusty/main Translation-en [762 kB]
Fetched 1922 kB in 2s (942 kB/s)
Reading package lists... Done

$ sudo chroot rootfs-trusty apt-get install udev
Reading package lists... Done
Building dependency tree... Done
The following extra packages will be installed:
  libudev1
The following packages will be upgraded:
  libudev1 udev
2 upgraded, 0 newly installed, 0 to remove and 84 not upgraded.
Need to get 768 kB of archives.
After this operation, 9216 B of additional disk space will be used.
Do you want to continue? [Y/n]
Get:1 http://ftp.byfly.by/ubuntu/ trusty-updates/main udev amd64 
204-5ubuntu20.19 [735 kB]
Get:2 http://ftp.byfly.by/ubuntu/ trusty-updates/main libudev1 amd64 
204-5ubuntu20.19 [33.8 kB]
Fetched 768 kB in 0s (2574 kB/s)
perl: warning: Setting locale failed.
perl: warning: Please check that your locale settings:
 LANGUAGE = "en_US",
 LC_ALL = (unset),
 LC_TIME = "be_BY.UTF-8",
 LC_MONETARY = "be_BY.UTF-8",
 LC_ADDRESS = "be_BY.UTF-8",
 LC_TELEPHONE = "be_BY.UTF-8",
 LC_NAME = "be_BY.UTF-8",
 LC_MEASUREMENT = "be_BY.UTF-8",
 LC_IDENTIFICATION = "be_BY.UTF-8",
 LC_NUMERIC = "be_BY.UTF-8",
 LC_PAPER = "be_BY.UTF-8",
 LANG = "en_US.UTF-8"
    are supported and installed on your system.
perl: warning: Falling back to the standard locale ("C").
locale: Cannot set LC_CTYPE to default locale: No such file or directory
locale: Cannot set LC_MESSAGES to default locale: No such file or directory
locale: Cannot set LC_ALL to default locale: No such file or directory
E: Can not write log (Is /dev/pts mounted?) - openpty (2: No such file or 
directory)
(Reading database ... 11517 files and directories currently installed.)
Preparing to unpack .../udev_204-5ubuntu20.19_amd64.deb ...
Adding 'diversion of /bin/udevadm to /bin/udevadm.upgrade by fake-udev'
Unpacking udev (204-5ubuntu20.19) over (204-5ubuntu20) ...
Preparing to unpack .../libudev1_204-5ubuntu20.19_amd64.deb ...
Unpacking libudev1:amd64 (204-5ubuntu20.19) over (204-5ubuntu20) ...
Processing triggers for ureadahead (0.100.0-16) ...
Setting up libudev1:amd64 (204-5ubuntu20.19) ...
Setting up udev (204-5ubuntu20.19) ...
Installing new version of config file /etc/init/udev-fallback-graphics.conf ...
initctl: Unable to connect to Upstart: Failed to connect to socket 
/com/ubuntu/upstart: Connection refused
 * udev requires a mounted procfs, not started
   ...fail!
invoke-rc.d: initscript udev, action "restart" failed.
dpkg: error processing package udev (--configure):
 subprocess installed post-installation script returned error exit status 1
Processing triggers for libc-bin (2.19-0ubuntu6) ...
Processing triggers for ureadahead (0.100.0-16) ...
Errors were encountered while processing:
 udev
E: Sub-process /usr/bin/dpkg returned an error code (1)

ProblemType: Bug
DistroRelease: Ubuntu 16.04
Package: udev 229-4ubuntu4
ProcVersionSignature: Ubuntu 4.4.0-18.34-generic 4.4.6
Uname: Linux 4.4.0-18-generic x86_64
ApportVersion: 2.20.1-0ubuntu2
Architecture: amd64
CurrentDesktop: Unity
CustomUdevRuleFiles: 99-vmware-scsi-udev.rules
Date: Mon Apr 18 12:25:46 2016
InstallationDate: Installed on 2016-04-15 (2 days ago)
InstallationMedia: Ubuntu 16.04 LTS "Xenial Xerus" - Beta amd64 (20160415)
Lsusb:
 Bus 001 Device 001: ID 1d6b:0002 Linux Foundation 2.0 root hub
 Bus 002 Device 003: ID 0e0f:0002 VMware, Inc. Virtual USB Hub
 Bus 002 Device 002: ID 0e0f:0003 VMware, Inc. Virtual Mouse
 Bus 002 Device 001: ID 1d6b:0001 Linux Foundation 1.1 root hub
MachineType: VMware, Inc. VMware Virtual Platform
ProcKernelCmdLine: BOOT_IMAGE=/boot/vmlinuz-4.4.0-18-generic 
root=UUID=fe0efb9a-7b87-4bb9-b308-3892f5d59d1b ro quiet splash
SourcePackage: systemd
UpgradeStatus: No upgrade log present (probably fresh install)
dmi.bios.date: 07/02/2015
dmi.bios.vendor: Phoenix Technologies LTD
dmi.bios.version: 6.00
dmi.board.name: 440BX Desktop Reference Platform
dmi.board.vendor: Intel Corporation
dmi.board.version: None
dmi.chassis.asset.tag: No Asset Tag
dmi.chassis.type: 1
dmi.chassis.vendor: No Enclosure
dmi.chassis.version: N/A
dmi.modalias: 
dmi:bvnPhoenixTechnologiesLTD:bvr6.00:bd07/02/2015:svnVMware,Inc.:pnVMwareVirtualPlatform:pvrNone:rvnIntelCorporation:rn440BXDesktopReferencePlatform:rvrNone:cvnNoEnclosure:ct1:cvrN/A:
dmi.product.name: VMware Virtual Platform
dmi.product.version: None
dmi.sys.vendor: VMware, Inc.

** Affects: systemd (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug xenial

** Description changed:

  $ sudo debootstrap trusty rootfs-trusty http://ftp.byfly.by/ubuntu
- I: Retrieving Release 
- I: Retrieving Release.gpg 
+ I: Retrieving Release
+ I: Retrieving Release.gpg
  I: Checking Release signature
  I: Valid Release signature (key id 790BC7277767219C42C86F933B4FE6ACC0B21F32)
- I: Retrieving Packages 
- I: Validating Packages 
+ I: Retrieving Packages
+ I: Validating Packages
  I: Resolving dependencies of required packages...
  I: Resolving dependencies of base packages...
  I: Checking component main on http://ftp.byfly.by/ubuntu...
  I: Retrieving adduser 3.113+nmu3ubuntu3
  
  ...
  
  I: Configuring ubuntu-minimal...
  I: Configuring libc-bin...
  I: Configuring initramfs-tools...
  I: Base system installed successfully.
  
- 
  Now add trusty-updates to sources.list:
  
  $ cat rootfs-trusty/etc/apt/sources.list
  deb http://ftp.byfly.by/ubuntu trusty main
  deb http://ftp.byfly.by/ubuntu trusty-updates main
  
  Update & upgrade:
  
  $ sudo chroot rootfs-trusty apt-get update
  Ign http://ftp.byfly.by trusty InRelease
  Get:1 http://ftp.byfly.by trusty-updates InRelease [65.9 kB]
- Hit http://ftp.byfly.by trusty Release.gpg           
- Hit http://ftp.byfly.by trusty Release               
+ Hit http://ftp.byfly.by trusty Release.gpg
+ Hit http://ftp.byfly.by trusty Release
  Get:2 http://ftp.byfly.by trusty-updates/main i386 Packages [718 kB]
  Get:3 http://ftp.byfly.by trusty-updates/main Translation-en [376 kB]
- Hit http://ftp.byfly.by trusty/main i386 Packages             
+ Hit http://ftp.byfly.by trusty/main i386 Packages
  Get:4 http://ftp.byfly.by trusty/main Translation-en [762 kB]
- Fetched 1922 kB in 2s (942 kB/s)                              
- Reading package lists... Done
- 
- $ $ sudo debootstrap trusty rootfs-trusty http://ftp.byfly.by/ubuntu
- I: Retrieving Release 
- I: Retrieving Release.gpg 
- I: Checking Release signature
- I: Valid Release signature (key id 790BC7277767219C42C86F933B4FE6ACC0B21F32)
- I: Retrieving Packages 
- I: Validating Packages 
- I: Resolving dependencies of required packages...
- I: Resolving dependencies of base packages...
- I: Checking component main on http://ftp.byfly.by/ubuntu...
- I: Retrieving adduser 3.113+nmu3ubuntu3
- 
- ...
- 
- I: Configuring ubuntu-minimal...
- I: Configuring libc-bin...
- I: Configuring initramfs-tools...
- I: Base system installed successfully.
- 
- 
- Now add trusty-updates to sources.list:
- 
- $ cat rootfs-trusty/etc/apt/sources.list
- deb http://ftp.byfly.by/ubuntu trusty main
- deb http://ftp.byfly.by/ubuntu trusty-updates main
- 
- Update & upgrade:
- 
- $ sudo chroot rootfs-trusty apt-get update
- Ign http://ftp.byfly.by trusty InRelease
- Get:1 http://ftp.byfly.by trusty-updates InRelease [65.9 kB]
- Hit http://ftp.byfly.by trusty Release.gpg           
- Hit http://ftp.byfly.by trusty Release               
- Get:2 http://ftp.byfly.by trusty-updates/main i386 Packages [718 kB]
- Get:3 http://ftp.byfly.by trusty-updates/main Translation-en [376 kB]
- Hit http://ftp.byfly.by trusty/main i386 Packages             
- Get:4 http://ftp.byfly.by trusty/main Translation-en [762 kB]
- Fetched 1922 kB in 2s (942 kB/s)                              
+ Fetched 1922 kB in 2s (942 kB/s)
  Reading package lists... Done
  
  $ sudo chroot rootfs-trusty apt-get install udev
  Reading package lists... Done
  Building dependency tree... Done
  The following extra packages will be installed:
-   libudev1
+   libudev1
  The following packages will be upgraded:
-   libudev1 udev
+   libudev1 udev
  2 upgraded, 0 newly installed, 0 to remove and 84 not upgraded.
  Need to get 768 kB of archives.
  After this operation, 9216 B of additional disk space will be used.
- Do you want to continue? [Y/n] 
+ Do you want to continue? [Y/n]
  Get:1 http://ftp.byfly.by/ubuntu/ trusty-updates/main udev amd64 
204-5ubuntu20.19 [735 kB]
  Get:2 http://ftp.byfly.by/ubuntu/ trusty-updates/main libudev1 amd64 
204-5ubuntu20.19 [33.8 kB]
- Fetched 768 kB in 0s (2574 kB/s)    
+ Fetched 768 kB in 0s (2574 kB/s)
  perl: warning: Setting locale failed.
  perl: warning: Please check that your locale settings:
-       LANGUAGE = "en_US",
-       LC_ALL = (unset),
-       LC_TIME = "be_BY.UTF-8",
-       LC_MONETARY = "be_BY.UTF-8",
-       LC_ADDRESS = "be_BY.UTF-8",
-       LC_TELEPHONE = "be_BY.UTF-8",
-       LC_NAME = "be_BY.UTF-8",
-       LC_MEASUREMENT = "be_BY.UTF-8",
-       LC_IDENTIFICATION = "be_BY.UTF-8",
-       LC_NUMERIC = "be_BY.UTF-8",
-       LC_PAPER = "be_BY.UTF-8",
-       LANG = "en_US.UTF-8"
-     are supported and installed on your system.
+  LANGUAGE = "en_US",
+  LC_ALL = (unset),
+  LC_TIME = "be_BY.UTF-8",
+  LC_MONETARY = "be_BY.UTF-8",
+  LC_ADDRESS = "be_BY.UTF-8",
+  LC_TELEPHONE = "be_BY.UTF-8",
+  LC_NAME = "be_BY.UTF-8",
+  LC_MEASUREMENT = "be_BY.UTF-8",
+  LC_IDENTIFICATION = "be_BY.UTF-8",
+  LC_NUMERIC = "be_BY.UTF-8",
+  LC_PAPER = "be_BY.UTF-8",
+  LANG = "en_US.UTF-8"
+     are supported and installed on your system.
  perl: warning: Falling back to the standard locale ("C").
  locale: Cannot set LC_CTYPE to default locale: No such file or directory
  locale: Cannot set LC_MESSAGES to default locale: No such file or directory
  locale: Cannot set LC_ALL to default locale: No such file or directory
  E: Can not write log (Is /dev/pts mounted?) - openpty (2: No such file or 
directory)
  (Reading database ... 11517 files and directories currently installed.)
  Preparing to unpack .../udev_204-5ubuntu20.19_amd64.deb ...
  Adding 'diversion of /bin/udevadm to /bin/udevadm.upgrade by fake-udev'
  Unpacking udev (204-5ubuntu20.19) over (204-5ubuntu20) ...
  Preparing to unpack .../libudev1_204-5ubuntu20.19_amd64.deb ...
  Unpacking libudev1:amd64 (204-5ubuntu20.19) over (204-5ubuntu20) ...
  Processing triggers for ureadahead (0.100.0-16) ...
  Setting up libudev1:amd64 (204-5ubuntu20.19) ...
  Setting up udev (204-5ubuntu20.19) ...
  Installing new version of config file /etc/init/udev-fallback-graphics.conf 
...
  initctl: Unable to connect to Upstart: Failed to connect to socket 
/com/ubuntu/upstart: Connection refused
-  * udev requires a mounted procfs, not started
-    ...fail!
+  * udev requires a mounted procfs, not started
+    ...fail!
  invoke-rc.d: initscript udev, action "restart" failed.
  dpkg: error processing package udev (--configure):
-  subprocess installed post-installation script returned error exit status 1
+  subprocess installed post-installation script returned error exit status 1
  Processing triggers for libc-bin (2.19-0ubuntu6) ...
  Processing triggers for ureadahead (0.100.0-16) ...
  Errors were encountered while processing:
-  udev
+  udev
  E: Sub-process /usr/bin/dpkg returned an error code (1)
  
  ProblemType: Bug
  DistroRelease: Ubuntu 16.04
  Package: udev 229-4ubuntu4
  ProcVersionSignature: Ubuntu 4.4.0-18.34-generic 4.4.6
  Uname: Linux 4.4.0-18-generic x86_64
  ApportVersion: 2.20.1-0ubuntu2
  Architecture: amd64
  CurrentDesktop: Unity
  CustomUdevRuleFiles: 99-vmware-scsi-udev.rules
  Date: Mon Apr 18 12:25:46 2016
  InstallationDate: Installed on 2016-04-15 (2 days ago)
  InstallationMedia: Ubuntu 16.04 LTS "Xenial Xerus" - Beta amd64 (20160415)
  Lsusb:
-  Bus 001 Device 001: ID 1d6b:0002 Linux Foundation 2.0 root hub
-  Bus 002 Device 003: ID 0e0f:0002 VMware, Inc. Virtual USB Hub
-  Bus 002 Device 002: ID 0e0f:0003 VMware, Inc. Virtual Mouse
-  Bus 002 Device 001: ID 1d6b:0001 Linux Foundation 1.1 root hub
+  Bus 001 Device 001: ID 1d6b:0002 Linux Foundation 2.0 root hub
+  Bus 002 Device 003: ID 0e0f:0002 VMware, Inc. Virtual USB Hub
+  Bus 002 Device 002: ID 0e0f:0003 VMware, Inc. Virtual Mouse
+  Bus 002 Device 001: ID 1d6b:0001 Linux Foundation 1.1 root hub
  MachineType: VMware, Inc. VMware Virtual Platform
  ProcKernelCmdLine: BOOT_IMAGE=/boot/vmlinuz-4.4.0-18-generic 
root=UUID=fe0efb9a-7b87-4bb9-b308-3892f5d59d1b ro quiet splash
  SourcePackage: systemd
  UpgradeStatus: No upgrade log present (probably fresh install)
  dmi.bios.date: 07/02/2015
  dmi.bios.vendor: Phoenix Technologies LTD
  dmi.bios.version: 6.00
  dmi.board.name: 440BX Desktop Reference Platform
  dmi.board.vendor: Intel Corporation
  dmi.board.version: None
  dmi.chassis.asset.tag: No Asset Tag
  dmi.chassis.type: 1
  dmi.chassis.vendor: No Enclosure
  dmi.chassis.version: N/A
  dmi.modalias: 
dmi:bvnPhoenixTechnologiesLTD:bvr6.00:bd07/02/2015:svnVMware,Inc.:pnVMwareVirtualPlatform:pvrNone:rvnIntelCorporation:rn440BXDesktopReferencePlatform:rvrNone:cvnNoEnclosure:ct1:cvrN/A:
  dmi.product.name: VMware Virtual Platform
  dmi.product.version: None
  dmi.sys.vendor: VMware, Inc.

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https://bugs.launchpad.net/bugs/1571569

Title:
  Cannot upgrade udev in the debootstrapped environment

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