Bitbucket v4.10.1, Debian jessie.

[swift_bitbucket]

Bitbucket server is at v4.10.1, host OS is Debian jessie.

Should I attempt to upgrade Bitbucket first, then Debian, or Debian first, then Bitbucket?

[Julius Davies [bit-booster.com]]

I'd do Debian first.

After the Debian upgrade make sure your Git version is still compatible with your Bitbucket instance (both your 4.10.1 version and your target version for your upgrade).   Bitbucket 4.10.1 is new enough that it can probably support the latest Debian git version, but reverse is probably not true. Newer Bitbucket versions might not be willing to tolerate the ancient git versions that comes with older Debian.

You'll also need to make sure your Database version is compatible (assuming it runs on the same Debian machine as Bitbucket - but that's a rare scenario, most people run the DB on a separate machine).

Here is Bitbucket 4.10.X's platform guidance (e.g., supported Git versions and Database versions):

https://confluence.atlassian.com/bitbucketserver0410/supported-platforms-858573806.html

That page has also has dropdown menu on the top-right that you can use to quickly navigate to the similar document for the version of Bitbucket you're hoping to upgrade to.

Also, remember to take a backup of Bitbucket first before you upgrade!   Bitbucket upgrades are not reversible (you cannot rollback unless you took a backup immediately preceding the upgrade).

[swift_bitbucket]

Thanks so much for the quick reply! I will apologize in advance for my glaring inexperience.

Bitbucket, Git, and any database they're using are all running on the same Debian 8 server in VMware.

A few weeks ago, I tried just letting Debian do all its updates, at the popup prompt on login. That seemed to go badly. The Debian GUI would not load, and I ended up reloading from backup.

I'll try again this weekend, but may I impose on your experience with a couple more questions? Should I break the updates down into groups, to help me figure out which might be the issue? Or is the leap from 8 to 9 drastic enough that this approach isn't doable?

Thanks again for your time and patience!

Jeff

P.S. - Would you be interested in a few paid consultancy hours in the coming days?

[Julius Davies [bit-booster.com]]

Jumping from Debian 8 to 9 is worth a shot, but in the end if it doesn't work you might need to re-install everything from a fresh Debian 9 install.

For backing up Bitbucket in this situation, vmware snapshots are great, but I also recommend using the official "Bitbucket Server Backup Client" in parallel (use both backup methods).  This tool can also be used to transition to a new database server. Its documentation link is very useful:

https://confluence.atlassian.com/bitbucketserver/data-recovery-and-backups-776640050.html

(Note - if you're on Bitbucket Data Center then the official backup tool is not supported).

On to the Debian upgrade, have you made sure all your Debian 8 packages are on their latest patch versions before you attempt the full upgrade?  I haven't used Debian in over a decade, but I'm on Ubuntu and the command is the same:

sudo apt-get update

sudo apt-get dist-upgrade

Do that before adjusting /etc/apt/* to point to Debian 9.  Since it's an "verison 8 --to--> version 8 latest errata" upgrade its very likely to succeed.

Personally I wouldn't waste any time trying to run a "Debian 8" --> "Debian 9" upgrade in groups.   In my experience that is the road to madness.  Do it in a single shot, perhaps using the same two commands above I mentioned (but after editing /etc/apt/* to point to Debian 9).

What database are you using?  Postgres, Mysql, Mariadb, or some other?

p.s.  Sorry, I'm too busy to take on any consulting work at this time.  But we love it when people try our Bitbucket add-ons!  

https://marketplace.atlassian.com/search?query=bit-booster

Only our "Rebase Squash Amend" add-on costs money.

[swift_bitbucket]

Thanks!

This is going to take some study before I can reply.

I need to learn what "editing /etc/apt/* to point to Debian 9" means, and what it might imply re Bitbucket.

Meantime, if you know know anyone qualified and experienced in running Bitbucket on Debian, looking for some easy money, please send them my way :)

[Julius Davies [bit-booster.com]]

By that I mostly mean just editing this file:

/etc/apt/sources.list

And search & replace every occurrence of "jessie" with "stretch".  But it's worth taking a look at every file under "/etc/apt" just to see if any other config also references "jessie" in there.  

NOTE:  if you see the word "stable" in there, change it to "jessie" before attempting to bring your current "jessie" to its latest patch versions.   (The "stable" pointer now points at Debian 9 instead of Debian 8 like it used to).

Also, if you see the words "unstable" or "testing" in there, proceed with caution, they might be contributing to a bit of a package mess.  Probably replace occurrences of "unstable" or "testing" with "jessie" as well.

Here's more information about the "stable", "testing", and "unstable" labels:  https://www.debian.org/releases/

Good luck!

[swift_bitbucket]

Ok, thanks. It looks like sources.list refers exclusively to "jessie", with nothing saying "stable", "testing", or "unstable" anywhere in it.

No other file in "/etc/apt" mentions any version, except java-8-debian.list in "/etc/apt/sources.list.d", which I don't think comes into play here.

I'm probably mistaken about the version targeted by my previous update attempt. I'm going to spend some time reading, and try again Saturday, and watch more carefully as things proceed.

Many thanks!

Jeff