> If you hit this on an upgrade from 3.x -> 3.x that would be wrong -
did you?.

yes, the log says it was an upgrade from 
3.1.0-3ubuntu0.1 
to
3.1.0-3ubuntu0.2


/var/log# grep post dpkg.log.1
2017-12-19 12:56:30 upgrade postfix:amd64 3.1.0-3ubuntu0.1 3.1.0-3ubuntu0.2
2017-12-19 12:56:30 status half-configured postfix:amd64 3.1.0-3ubuntu0.1
2017-12-19 12:56:32 status unpacked postfix:amd64 3.1.0-3ubuntu0.1
2017-12-19 12:56:32 status half-installed postfix:amd64 3.1.0-3ubuntu0.1
2017-12-19 12:56:33 status half-installed postfix:amd64 3.1.0-3ubuntu0.1
2017-12-19 12:56:33 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:56:33 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 configure postfix:amd64 3.1.0-3ubuntu0.2 <none>
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status unpacked postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:55 status half-configured postfix:amd64 3.1.0-3ubuntu0.2
2017-12-19 12:57:57 status installed postfix:amd64 3.1.0-3ubuntu0.2


> To do so it is in a guard like this:
>  if `dpkg --compare-versions "$2" lt 3.1.0-1~`; then


I guess here "$2" is the new version, this is what I can see on my machine:

# dpkg  --compare-versions 3.1.0-3ubuntu0.0  lt 3.1.0-3ubuntu0.1~; echo $?
0
# dpkg  --compare-versions 3.1.0-3ubuntu0.1  lt 3.1.0-3ubuntu0.1~; echo $?
1
# dpkg  --compare-versions 3.1.0-3ubuntu0.2  lt 3.1.0-3ubuntu0.1~; echo $?
1
# dpkg  --compare-versions 3.1.0-3ubuntu0.3  lt 3.1.0-3ubuntu0.1~; echo $?
1


it returns true at each update, but i don't know what you have in the 'then' 
part

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Title:
  SSL issue upgrading postfix

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