Lion Server to Mavericks Server Upgrade

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Level 1

9 points

Lion Server to Mavericks Server Upgrade

I spoke to an Apple Tech (Enterprise Support) who told me that the steps and process for upgrading from OS Lion Server to Mavericks server were fairly strait forward. I'd like to outline my understanding of those steps (building in some of my own) before moving forward here for feedback if anyone has any feedback. THIS IS NOT A TESTED PROCESS - SEE BELOW FOR FEEDBACK, IF ANY, BEFORE PROCEEDING:

1) Check Compatibilities

2) Rebuild permissions on target server from the recovery disk.

3) Run any/all patches/updates.

4) Backup via Time Machine - then by using a bare metal copy program (i.e. SuperDuper or Carbon Copy Cloner) to an external disk.

5) Test the backup.

6) If upgrading an OD Master follow these procedures first: http://support.apple.com/kb/HT5300

7) Stop all Server services/functions

8) Make sure that any DNS or DHCP servers that your server relies on remain running during the process. (Source)

9) Upgrade the OS on the target machine to the latest version of OS Mavericks via the App Store (making sure not to launch the Server App afterwards)

10) Upgrade the Server App to OS X Server (Currently V 3.1.2)

Acccording to Apple: "In most cases, your service data and settings will be preserved completely when upgrading or migrating."

11) Reboot

12) Rebuild permissions on target server from the recovery disk.

13) Turn SSL back on per http://support.apple.com/kb/HT5300 (Step 6) if needed.

14) Resume Core Services

Mac Pro, Mac OS X (10.7.3)

Posted on May 30, 2014 9:37 AM

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Answer 1

DOLAdmin Author

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9 points

Jun 3, 2014 7:33 AM in response to DOLAdmin

Wow - 50 views and NO ONE wants to touch this huh?... ^_^

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Answer 2

lawaidit

Level 1

8 points

Jun 3, 2014 11:50 AM in response to DOLAdmin

Well, today I'm scratching my head trying to figure out how to accomplish this if the server I want to upgrade is my DNS server. Upgrading to Mavericks will turn off the DNS server, which means I can't upgrade to Mavericks Server without setting up another DNS server? This seems like a really ungraceful upgrade path.

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Answer 3

Jun 16, 2014 5:42 PM in response to lawaidit

I've done the upgrade and it doesn't take very long and you won't lose your settings. You will, however, have to purchase the OS X Server app that runs on Mavericks. And, of course, your machine does have to reboot so your DNS would be down anyway. Unless you're serving a large system, I doubt you'll need to set up another DNS server. If your DNS server were so mission critical that it couldn't be down for no more than 30 minutes (which is more time than this actually takes) you'd already have one running as a slave.😉

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Answer 4

lawaidit

Level 1

8 points

Jun 17, 2014 7:26 AM in response to Iggy Pelman

The problem isn't DNS being down for the network during the upgrade, the problem is DNS being down for the server during the upgrade. Since it hosts its own DNS, and the DNS service is disabled when I upgrade to Mavericks, it can't resolve its hostname until after Server.app finishes updating things and starts the DNS service. The documentation clearly says that it must be able to resolve during the update process, hence the need of another DNS server. I don't want to muck up my Open Directory Master, so... second DNS server it is. But it's a really bothersome process.

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Answer 5

Jun 17, 2014 10:20 AM in response to DOLAdmin

Wow - 50 views and NO ONE wants to touch this huh?... ^_^

- I would suggest many who viewed this discussion were giving due considerations of all of the steps and options.

- Once there is a Time Machine backup and a clone backup on a disk in another bay.( using CCC or SD ) I would boot from the clone, check all is ok, then perform the upgrade on the clone disk.

- If any issues, there is the original untouched disk to recover from.

Cheers

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Answer 6

DOLAdmin Author

Level 1

9 points

Jun 17, 2014 1:37 PM in response to lawaidit

"...The documentation clearly says that it must be able to resolve during the update process..."?

Are you referring to this? OS X Server: Steps to take before upgrading or migrating the Open Directory database

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Answer 7

lawaidit

Level 1

8 points

Jun 17, 2014 1:44 PM in response to DOLAdmin

I feel like this is a trick question somehow, but... yes? I've seen it a few places around the kbase, the article you mentioned and also in the articles about upgrading/migrating from Lion/Mountain Lion to Mavericks. For example.

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Answer 8

DOLAdmin Author

Level 1

9 points

Jun 17, 2014 1:45 PM in response to dwbrecovery

Yes I'm sure... I was hoping that by now, someone would have been able to point us in the direction of a fairly well documented/tested upgrade guide. This may, in fact, be the first shot at one.

Iggy Pelman's comments above were encouraging...

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Answer 9

DOLAdmin Author

Level 1

9 points

Jun 17, 2014 1:47 PM in response to Iggy Pelman

Iggy -

Can you please comment on the process I've outlined above given your experience? Is it close - specifically items 6-10?

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Answer 10

Jun 17, 2014 5:38 PM in response to DOLAdmin

I guess, first, I should say that i upgraded the server that I was running my DNS & OD on and I had no problems with the install process itself, per se. And, I should also point out the I hummed and hawed about this upgrade for a while because I natually don't trust s/w upgrades involving both the os and the server s/w itself. But, after going through it I can say that the problems that I faced came after the fact - the DNS worked as well as it did before the upgrade, as did everything else. So, my best insights are...

1. Upgrading the OS was very straightforward. So much so that I can't remember having to do a whole lot other than to wait for it to conclude. Obviously, I would back things up and, if I were to do it again, I'd create an image on an external drive just in case.

2. Purchasing and installing the Server app was also straightforward. So much so that I really can't remember the details since it pretty much walks you right through it.

However, my issues on the other side, other than going through the withdrawl of not having a ServerAdmin app (or WG Manager), was mainly with OD. My recommendation is...

Like the support doc says, make sure your internal & external DNS are working properly. This is critical. If you have any errors in your log files, you'll want to address them. One thing I found is that the 192.168 subnet gave me problems. I migrated to a 10.0 (which fixed some problems but forced me to recreate OD - not a big prob for me as I have a realtively small system).
Make sure that System Preferences > Network Preferences > DNS Server on the actual DNS server (only) is set to 127.0.0.1 (not it's, hopefully, static IP).
If you are planning on doing anything such as change the subnet, FQDN, etc. do it BEFORE you upgrade. The only way you can fix the problems that I faced (see https://discussions.apple.com/thread/6382555?answerId=26141304022#26141304022) is to destroy and recreate OD. I obviously don't know your situation but mavericks relies more on OD than does Lion and, as such, File Sharing plays less of a role (IMHO). Your local users' email addresses will be useless as all email addresses are attached to Local Network Users. So I would suggest you prepare for that, if possible, by creating a LNU for every LU you have without creating a home directory - i.e. Services Only - and make the appropriate changes to user names etc. The only local user that I now have is whomever actually needs to login to the console - namely, me. Everyone else gets their services as Network Local Users.
I would suggest that stopping services is a good idea as this would ensure your system is in a stable state during the upgrade.
I run DHCP/NAT from an Airport Extreme so it was on the whole time and my server's IP is static (I already said that but it's worth repeating). If your'e running your DHCP from your server then you'll want to at least temporarily port it over to your router.
Probably a great idea not to attempt to launch an app that isn't supported by Mavericks. Frankly, as soon as I had finished the os upgrade I went straight to the Apple Store, bought the Server app, uttered some sort of plea to anyone who was listening to make this work and installed the new server app. It did.
They weren't lying. The data was completely preserved although in different locations in some cases. I suggest the first thing you do is to create an environment variable (call it $NAMED) pointing to your new /Library/Server/named directory, for instance. BTW, copies of the original (pre-upgrade) files are often created with the os version appended to their names.
After this experience, I'm absolutely sure that there is no need to create a slave DNS server in order to resolve anything. I'm guessing that whatever is required is handled by the DHCP router.

Hopes this both makes sense and helps. Good luck.

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Answer 11

DOLAdmin Author

Level 1

9 points

Jun 20, 2014 9:39 AM in response to Iggy Pelman

Yeah Iggy thanks - that was invaluable feedback and I (and I'm sure others) appreciate it. Like you were, I'm also in hum/haw mode at the moment. Fortunately for me I'm not hosting email or DHCP so... A little confused about point # 7 - the creation of an environment variable "$NAMED" pointing to my new /Library/Server/named directory but don't worry about responding further. I did see this on the subject and I'm not managing any variables.

Thanks again!

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Answer 12

DOLAdmin Author

Level 1

9 points

Jul 3, 2014 9:52 AM in response to DOLAdmin

So I successfully performed this update last night. Elapsed time - about 4 hrs. (most of that time was waiting for the Mavericks download and the pre-treatment stuff I outlined. Use at your own risk - no guarantees of course but overall I was delighted with the ease of the process.

1) Check Compatibilities

2) Rebuild permissions on target server - target disk - from the recovery disk.

3) Run any/all patches/updates.

4) If upgrading an OD Master follow these procedures: http://support.apple.com/kb/HT5300

5) Post updates permissions rebuild again on target server - target disk - from the recovery disk.

6) Backup via Time Machine - and a "bare metal" copy program (i.e. SuperDuper or Carbon Copy Cloner) to an external or separate internal disk.

7) Test the backups (the bare metal at least) - and not just successful boot. Test all services functionality, network configurations, web functions etc. Note: SuperDuper's performance was flawless.

8) OPTIONAL: Run all Apple updates and rebuild permissions on target server - MIRRORED DISK - from the recovery disk.

9) Boot back to your Target Disk

10) Stop all Server services/functions. I did NOT drop the server from the AD domain (though I DO do that for Lion to Mavericks WORKSTATION upgrades now)

11) Make sure that any DNS or DHCP servers that your server relies on remain running during the process. (Source)

12) Upgrade the OS on the target machine to the latest version of OS Mavericks via the App Store (making sure not to launch any legacy Server Apps afterwards - their icons were deprecated on the dock anyway)

GOTCHA ALERT: Be sure you have an Apple ID tied to a credit card setup on the machine you're updating. Otherwise you'll be asked to enter the CC security ID on the different machine. I was able to get around not having this available at the time of the update by going to the machine I enrolled the credit card under and buying/downloading OS X Server. Then I copied the installer to the target server - worked fine.

13) Check for any updates needed through the App Store. If any are needed - run those updates and again, reboot/rebuild permissions from the recovery disk.

14) Upgrade the Server App to OS X Server from the App Store

15) Reboot

16) Rebuild permissions on target server - target disk - from the recovery disk.

17) Turn SSL back on per http://support.apple.com/kb/HT5300 if applicable. (I forgot to do this).

18) Resume Core Services

*Acccording to Apple: "In most cases, your service data and settings will be preserved completely when upgrading or migrating." This proved to be true in my case.

** Watch for the deprecated ipfw firewall surprise at the end. Even though I tested SMB connectivity before leaving, users weren't able to log in next morning. I shut down the reported "legacy" ipfw firewall which was an option listed in the log as a first suspect and it worked. Firewall settings are retained (I determined by running a port scan) but see:

http://support.apple.com/kb/ht5413

http://support.apple.com/kb/HT200259

http://support.apple.com/kb/PH13892

Potential 3rd Party Firewall GUI for Mavericks as well - check compatibility: http://www.hanynet.com/icefloor/index.html

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Answer 13

DOLAdmin Author

Level 1

9 points

Jul 25, 2014 8:42 AM in response to DOLAdmin

UPDATE: So I thought I had updated the server successfully on JUL 3rd but by MID-JUL it became clear that underlying problems were coming to the surface. This is why you should strongly consider updating one server at a time and waiting before doing the next. Some problems take time to manifest. The problems I had were as follows:

1) About two weeks post upgrade, the server began freezing up - several mornings in a row. Shutting off Wiki Services (not used anyway) corrected that problem but still... Also noticed that managed Mac OS devices were having problems with connectivity as several users experienced extended stay "updating managed settings" dialog boxes on logins.

2) Right at about the same time, I noticed some of the server's file sharing processes had decayed. For example, I was unable to add new accounts, controls were grayed out and there were various problems with connectivity - even after a reboot.

I decided right then and there to roll back to the Lion Server mirror I created/tested before doing the upgrade. Interestingly, after that, I also had to drop/add the machine from AD to smooth it out since the path to the DC needed to be re-mapped- no problems since.

Prior to roll-back, I called Apple Enterprise support and the first technician I spoke to seemed quick to suggest blowing away profile manager/reinstalling (sent instructs) or - reinstalling Server App completely (as if they've heard plenty of these calls). Called the next day to get a 2d opinion from a different tech who seemed more willing to troubleshoot the installation but he eventually decided to defer the call to a "Senior" Tech Manager after a thorough DNS systems check yielded nothing. The Sr. Tech was supposed to call within 24-48 hrs. That call hasn't come (although I have an open ticket number). This tells me Apple Enterprise support is likely inundated with server related problems and that they'd rather see you reinstall Profile Manager or the entire Server App.

I should point out in all fairness that in all likelihood, a CLEAN server build from bare metal is probably a best case scenario opposed to an upgrade to an existing, matured and possibly bloated Lion box. In fact, A Mountain Lion Server upgrade to Mavericks server, may have a much better outcome given the tighter lineage. None the less and IMHO, Apple still has a ways to go with ensuring that a server upgrade won't take down a production (corporate) machine. Even with all of the pre-prep stuff I listed above - these problems STILL occurred. So backup, backup, backup first.

For my next act I will very likely start with a clean install of Mavericks - install Server App and configure from there. That will force me to have to re-enroll all my Mac OS clients again and over time but I'd rather do that for the benefit of all the new features the newer platform offers anyway.

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