Force Yosemite Update

Any reason you don't just drop the install on the machine and force it? I don't know of any way to force the install from the App store but have had success running the install as a Policy with Casper.
http://www.jamfsoftware.com/resources/deploying-os-x-v10-7-or-later-with-the-casper-suite/

Half of my users are remote and work from home so they are on Wifi most of the time and never get on VPN. I would have to use Amazon to distribute the package or have them get it from the App Store. Figured it was easier to download from the App Store haha.

Makes sense. Maybe someone else can help you out. Sorry bud.

In order for this to work, you would need a cloud distribution point, and for the machines to check in at least one more time to get new policy and server instructions. You may need to consider checking that box in the General tab that makes the policy "available offline."

There would be one policy that caches the installer from the cloud DP. And then another policy that does an "Install Cached" of the Yosemite package after downloading.

But all in all this sounds like trying to solve a social problem with a technical one. Why not have management send out a communication that instructs users to download Yosemite?

My concern about "forcing" an OS upgrade is that the user has to be a willing participant, and if they aren't, they could irrevocably damage their OS and potentially lose data by trying to stop it.

For that reason, we steer users to the App Store because we know they can get the installer from pretty much anywhere they are. We don't currently have HTTPS on our DPs so pushing a download of the app without resume capabilities could end poorly.

Having Office 2016 require Yosemite provides a great carrot.

@alexjdale. Precisely. If the users are running severely outdated installations of Mac OS X, there needs to be an executive decision by the IT Director / CTO, with upper management signoff, that says something like "users will not be supported until they upgrade the software or get new computers" (if there is an existing lifecycle policy in place).

You could always use the software update command line tool.

"softwareupdate -l" will list out all available updates.

Then you could use "softwareupdate -i package name" to install the specific update

We instruct our remote users to connect their MBP's to the internet and connect to our internal network with Global Protect. Once their Mac checks in, the Yosemite installer caches from Casper. Once completed, the inventory is updated and remote user can install from Self Service.

Most of the users im targeting are on 10.9.5 still. None of them are more outdated than that. our big thing is wanted to get them updated so they can get Office 2016.

Why not offer this in Self Service? I would have to agree that forcing a full OS upgrade isn't necessarily a good thing and could cause you some troubles. I would make it an opt in method, but promote it heavily. We have a policy that runs a few times a week that pops up a jamfHelper message explaining that our Yosemite upgrade is available in Self Service. One of the buttons in the dialog when clicked will start the upgrade enrollment process right away so its easy for users to start it.

As has been mentioned, there is no current way to install something like an OS upgrade from the App Store. You can install regular system updates in the background with softwareupdate, but not the full OS update.

Ive tried everything to offer it to them. They just don't care about it lol. Offering them no support if they dont do it they dont care. They just dont do the upgrade. We have even tried to schedule times to do it for them and they never come into the office or let us remote in to start the update. Kinda fighting a losing battle lol.

I have seen a policy adopted whereby Self Service would not work on anything but the latest (or latest but one) version of the OS.

Shawn,

Ah, so you are trying to solve a social problem. People are inherently lazy; they need a reason to upgrade. They also don't like being "managed." You have to reframe it as "hey, look at all this cool software you can get from the self service portal!"

How many employees are at this company, if you don't mind my asking?

Have you or your bosses sent out any type of communication about the upgrades? What is the tone of those messages?

What is the reason for trying to push Office 2016?

Have you explained to the users that it runs so much better than Office 2011, especially Outlook?

Like @bradtchapman has mentioned, you need to start thinking about the carrot approach. Dangle the prospect of a much better email experience with Office/Outlook 2016 in front of them to see if they bite. If they do, at that point you can explain in as nice a way as possible that to use the software its a requirement to be on the latest OS. Not your requirement, but Microsoft's. Make the actual upgrade process as easy as you can possibly make it for them to do. Click a button, let your Mac reboot and the OS gets upgraded kind of thing. Its possible to do.

Also, its an interesting situation you have. We seem to have exactly the opposite problem. Trying to convince users not to immediately upgrade to the latest release of any particular item is difficult for us, and we sometimes have to take the measure of blocking things. I can almost guarantee you that 5 minutes after El Capitan shows up in the Mac App Store, we will see some users trying to download and install it. Some of them seem to like to be on the bleeding edge (emphasis on "bleeding"). I've yet to see a 10.x.0 release from Apple that isn't buggy and painful until it hits around the x.x.3 mark, so I'm often baffled why they want to do this to themselves. And then there is 3rd party software compatibility issues. I won't even go there.