Debian jessie to stretch server upgrade notes

I did basic workstations here (my blog) and there (my blog) note the networking issues which is also pertinent to servers Some workstation issues of help discovered early on where

virtual box

Needs help form the incompetent fools at oracle (see wiki) as the kernel modules are now outside the remit of debian support – speaks volumes of oracle.whom generally turn most things into a disaster like java (my blog).- can you wean me off virtualbox with some other manager suggestions welcome in comments.


needs a grub config line and a TTYVTDisallocat=no in otherwise you have no idea if it works or not.when loading you get some messages but without systemd config you will know about a few things see the wiki to set up [not hard]

The server entailed lots of backups and copies of old data all over the place just in case thing go wrong.

Day 1:

After backups change your sources file to stretch, update and apt -f full-update..2784 packages later (3 hours) i had a debian stretch os installed, cannot really call it a server though as fail2ban, postfix, imap and apache barely work.

dns,postgresql and ssh kind of worked though

Sisyphus is still a role model

I think upgrading from i386 to i686 caused the zoo a lot of issues, apt autoremove did not help and i had to remove over a two hundred remains of jessie packages.via aptitude.

Apache2 – cant do cgi and my cgi files did work in jessie

Fail2ban – honestly no idea what is happening here, deinstalled it

Postfix – missing loading four other postfix instances

Opendmarc – is mia

Cyrus – the jump from 2.4 to 2.5 means foo becomes foo_bar – your config files need massive changes, need to reconstuct databases too.   if you know what a DBERROR db5 is then your doing better than i am

Good news printing (cups) works and networking [see above link] survived.  I considered that a win

Day 2

With a fresh pair of eyes, i ‘fix’ crappy virtual box and discover to my delight that the zoo’s cron jobs still work.   I need to remove that trash for something better that does a virtual memory space when i test things.

Cyrus Imap

Gets weirder and werieder

  • it listens on http port 8008.(REALLY)
  • mboxlist and deliver commands seem to be not used
  • sasl logins are from the twilight  zone

I got a paired down (brand new config) that kind of works although three zoo domains cannot open the mail.



goes to version three expect to use one of these (not here)  If like the zoo you have more than more postfix instance then your need systemd to start it as the init.d scipt is dancing with the faeries and now only loads /etc/postfix.


defaultseedonly becomes testonly – spf has to have some kind of issue and alert you about with debian upgrades or you never know your doing one.

Day 2 was kind of a success.  Even if the mail was flowing in via my actions rather than a systemd startup action and postfix and cyrus kind of work i think.

I began to feel that debain might work rather than simply tell me that estortic_command_lines may have changed.

Day 3:


Issues are caused by old sockets in cyrus.  Go to your imap mail store directory and the sockets directory and delere.  I did not have to delete *.db’s but even after a reconstruction its not explictly something advertised.   – I appear to be able to receive and process inbound mail

postfix systemd

With the magic of a console i started other instances of postfix and it appears to work my additional systemd scripts dont work one shows a bash shell and the others no bash shell – i hate systemd.- i might need postfix-multi but do not like the idea of it with my existing config,

Day 4

Good news first – amavis seems to work no issues, and now back to problems

apache cgi/mailgraph

I have weird apache error codes but not a meaning as to what they mean i think

  • ah000128 start
  • ah000169 restart
  • ah001909  ssl mismatch (warn)
  • ah002811 script alias issue ?
  • ah000094 ?

google searching for those is a miss they like 404 error codes  – cgi is well broken but that seems down to perl -i had to get rid of perl -wT and run perl -w so getting there.

Moving mailgraph.cgi to cgi-bin fixes the issue (we just need the images which are called via javascript url method).  I gave up /usr/lib/cgi-bin and did cgi-bin my own way.


appears to work unhindered like Jessie not a fuckup


Apparently does work – just reconfigure from scratch


version 9.10 apparently means it now do caa records without encoding, it has a geoip feature that it loves to advertise.


worst thing: cyrus imap

less worst thing perl ‘changes’ (cgi)

stuff to still fix

  • clean out etc old entries
  • postfix start up ‘issues’
  • remove on disk backups
  • opendmarc reporting is not working
  • check email sending with dkim (works locally)
  • postgresql 9.4 refuses to load but the 9,6 version means i do not have load it twice – a bit botched but progress

notable mentions to spf – good to see that i still had to change something.

Hope that has not put you off but that was my rather fraught upgrade experience.  Perhaps i should have gone from Jessie i386 to 686 and then to Stretch.

I can work on the issues at a more leisurely pace now

The pingbacks to this site below update on this post and resolve issues i had.

6 responses

  1. Pingback: Further Debian Stretch as a server notes | Bananas in the Falklands

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  3. Pingback: opendmarc in debian stretch | Bananas in the Falklands

  4. Pingback: apache2-doc debian weirdness fixed | Bananas in the Falklands

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