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How do I upgrade to macOS Server from a server running OS X 10.9.5 and OS X Server 3.2.2? I would assume that I simply upgrade the OS X to macOS, then buy/download/install the macOS Server app from App Store. Of course, I will have a full backup of server before taking these steps.

Currently, we are only using the server for File Sharing and Time Machine. Am I missing any other steps? After upgrading, should my existing file shares and Time Machine backup still be configured as before?

I tried to upgrade to macOS Sierra and got this message:

macOS Sierra supports macOS Server version 5.2. To upgrade your Server data you will first need to install OS X 10.10 or 10.11 and OS X Server version 4 or 5. Installing macOS Sierra on this volume will disable the current server functionality. Are you sure you want to continue the installation?

I am unable to find OS X 10.10 or 10.11 in the App Store. If I continue installation, and then upgrade to macOS Server, will I have to reconfigure my server or will it be upgraded?

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I successfully could upgrade server 3.2.2 (osx10.9.5) to macos server 5.2 (sierra) on my mac mini by following steps.

  1. Install Yosemite to your mac.

  2. Purchase Server 5.2 with your Apple ID. You can buy it on the mac 10.11.6 or later.

  3. Open App Store. Select Server 5.2 and Press INSTALL button. The operation leads to install Server 5.0.15 !!!

  4. Launching Server 5.0.15 will proceed the migration process.

  5. And then install Sierra and Server5.2.

More info in my weblog below (in Japanese...) http://memorandums.hatenablog.com/entry/2016/10/26/220901

  • Thanks for the answer. I ended up calling Apple and they gave me these exact steps, but I didn't have time to come back and post the answer. Following these steps solves the problem. – Swisher Sweet Oct 26 '16 at 18:01
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You should be able to update normally without any problems. I don't think there's anything you are missing.

Edit:

According to the error message, it seems you will first need to install "OS X 10.10 or 10.11 and OS X Server version 4 or 5" on your server. Then try upgrading again. If you continue right now, your current server will be disabled, and you will have to try to restore your server.

  • Thanks for the answer. I ran into a warning and updated my question with the details. Do you know if this will cause me any issues if I continue? – Swisher Sweet Oct 25 '16 at 0:39
  • I've edited my answer to answer your question – abc Oct 25 '16 at 1:00
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If you are running 10.9 Mavericks, you may need to upgrade to Yosemite first (e.g. from 10.9.5->10.10.5->10.11.6, or 10.9.5->10.10.5->10.12.x) instead of skipping versions (e.g. 10.9.5->10.11.6 or 10.9.5->10.12) if you want to upgrade Server settings.

Server settings on a Mac Mini Server will not update directly from 10.9.5 Server.app version 3.2.2 to Server 5.1.7 for El Capitan 10.11.6. You get an error when running Server 5.1.7 and clicking Continue to upgrade, saying the settings are too old to upgrade. I had to first update from Mavericks to Yosemite, which required that I disconnect from the network and set the clock back to 2014 to get the old Yosemite to "verify" and install. After Yosemite 10.10.5 was installed, I upgraded Server.app to version 5.0.15 (the iTunes app store asked if I wanted to download an older version, since the Server 5.2 for Sierra 10.2 is already out).

Once Server.app 5.0.15 was installed in Yosemite, I ran it to update the services and checked that all the settings for Users, File Sharing, DNS and other services are there. I then updated to El Capitan (10.11.6), upgraded Server.app to version 5.1.7 and ran it to update the services again. I don't plan to update this server to Sierra yet, since the office has some older Macs that won't run Sierra, so all the Macs will use El Capitan for now.

According to KB HT207027 (https://support.apple.com/en-us/HT207027), Server.app for macOS Sierra 10.12 supports migrating Server data from Yosemite 10.10.5 and Server 5.0.15, or El Capitan 10.11.6 and Server 5.1.7, so you can skip a version with Sierra, but not for El Capitan.

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I had the same problem.

OS 10.9.5 running Server 3.2.2

The answer was install 10.10.5 one way or another (purchases tab from app store is best if available). This will stop 3.2.2 from working in the meantime.

Then buy latest Server 5.x on another mac running something new like Sierra using the same apple ID.

Then install it on the older mac from the purchases tab will give you 5.0.15 which can upgrade and bring across settings from 3.2.2

Then install Sierra and do the upgrade to the latest 5.x

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I did similar thing except I upgraded from El Capitan. Shouldn't need to worry about anything, upgrade to Sierra and get Server 5.2. Remember you can always go back to a backup if you mess up.

EDIT: Yep, I saw your warning, I also got that warning when updating from 10.11, just install Server app 5.2 and you're fine. Older version of Server app is not supported on newer system. If this doesn't work, update to 10.11 from here, then download Server 5.1.5 through the App Store, after setting up, upgrade to Sierra and Server 5.2

  • Thanks for the answer. I ran into a warning and updated my question with the details. Since you upgraded from El Capitan, I presume you didn't run into this issue. – Swisher Sweet Oct 25 '16 at 0:40
  • @SwisherSweet what is the warning – Tom Shen Oct 25 '16 at 2:07
  • I posted the warning in my question via an edit. – Swisher Sweet Oct 25 '16 at 14:21
  • @SwisherSweet I saw it, read the edit :) – Tom Shen Oct 25 '16 at 14:40
  • Thanks Tom. I did read your edit, however the message clearly states "To upgrade your Server data you will first need to install OS X 10.10 or 10.11 and OS X Server version 4 or 5." If I don't do this first, won't I have to reconfigure my server again? – Swisher Sweet Oct 25 '16 at 14:46

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