Hi,
Nish is right, this This appears to be a syntax error wrt. to python3.

Orig Xenial release
2:4.3.8+dfsg-0ubuntu1
Current Xenial
2:4.3.11+dfsg-0ubuntu0.16.04.3

And the error seems on pre-removal script according to the log:
dpkg: warning: subprocess old pre-removal script returned error exit status 1
dpkg: trying script from the new package instead ...
  File "/usr/bin/pyclean", line 63
    except (IOError, OSError), e:

In the reported case the versions were:
Reporter prior to update
2:4.3.9+dfsg-0ubuntu0.16.04.2
Trying to update to:
4.3.11+dfsg-0ubuntu0.16.04.1

But just as Nish assumed I think we do not have to look at the samba
versions too much, essentially the bug is in /usr/bin/pyclean which is
part of "python-minimal".

And in fact the line:
   except (IOError, OSError), e:
Gets highlighted by syntax checkers as:
"Python 3.x incompatible 'except x,y:' construct [H231]"

The code is still as-is on Zesty with #! /usr/bin/python.

I'd assume this only triggers when the system is tweaked to run /usr/bin/python 
as python3?
Does that match your case?

Quick verify:
$ python2.7 /usr/bin/pyclean 
Usage: pyclean [-p PACKAGE] [DIR_OR_FILE]

$ python3.5 /usr/bin/pyclean 
  File "/usr/bin/pyclean", line 63
    except (IOError, OSError), e:
SyntaxError: invalid syntax

Therefore I'd file it against python-defaults and subscribe Barry as he
is way deeper into the future of py2/py3 transition.

** Tags removed: bitesize xenial

** Summary changed:

- package python-samba 2:4.3.9+dfsg-0ubuntu0.16.04.2 failed to install/upgrade: 
subprocess new pre-removal script returned error exit status 1
+ /usr/bin/pyclean fails with python3

** Also affects: python-defaults (Ubuntu)
   Importance: Undecided
       Status: New

** Changed in: python-defaults (Ubuntu)
   Importance: Undecided => High

-- 
You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to python-defaults in Ubuntu.
https://bugs.launchpad.net/bugs/1633331

Title:
  /usr/bin/pyclean fails with python3

Status in python-defaults package in Ubuntu:
  New
Status in samba package in Ubuntu:
  Triaged

Bug description:
  samba

  ProblemType: Package
  DistroRelease: Ubuntu 16.04
  Package: python-samba 2:4.3.9+dfsg-0ubuntu0.16.04.2
  ProcVersionSignature: Ubuntu 4.4.0-36.55-generic 4.4.16
  Uname: Linux 4.4.0-36-generic i686
  NonfreeKernelModules: wl
  ApportVersion: 2.20.1-0ubuntu2.1
  Architecture: i386
  Date: Fri Oct 14 08:31:48 2016
  ErrorMessage: subprocess new pre-removal script returned error exit status 1
  InstallationDate: Installed on 2016-08-05 (69 days ago)
  InstallationMedia: Ubuntu 14.04 LTS "Trusty Tahr" - Release i386 (20140417)
  NmbdLog:
   
  RelatedPackageVersions:
   dpkg 1.18.4ubuntu1.1
   apt  1.2.12~ubuntu16.04.1
  SambaServerRegression: Yes
  SmbConfIncluded: Yes
  SmbLog:
   
  SourcePackage: samba
  Title: package python-samba 2:4.3.9+dfsg-0ubuntu0.16.04.2 failed to 
install/upgrade: subprocess new pre-removal script returned error exit status 1
  UpgradeStatus: Upgraded to xenial on 2016-08-06 (68 days ago)
  WindowsFailedConnect: Yes

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