Office 2019 OEM via Dell Digital Delivery and WIndows SYSPREP

Sysprep and imaging is only permitted via Volume License.  If you purchased an OEM license for office, you cannot include that in the image.  You would have to have Dell configure the machines and ship them with it pre-loaded or you would need to install it on each machine individually.  All users would need an Office Volume License, but only one Windows Volume license would be required.

Because OEM doesn't qualify for deployment, it's reactions to being sysprep cannot be known/guaranteed and we can't help with it.

Licensing Disclaimer
License information provided here is "best efforts".  The comments of the respondents are based on interpretation of the license agreements and their knowledge of the particular laws and regulations in their geographic location.  Laws in your location may invalidate certain aspects of the license and/or licenses can change.  (For example, at least one major nation's laws allow OEM licenses to be transferred to new hardware). "They told me on Experts-Exchange" will not be a valid excuse in an audit.  You need to contact the license granting authority to confirm any advice offered here.

Anybody with actual information or experience?

Experience with violating licensing?

I did not respond to your earlier post Lee but I will now: There is no license violation since the workstations were all purchased from Dell with Office OEM included on each system. That has been confirmed with both Dell and the Dell Microsoft Licensing desk. Yes, we do indeed own a volume license for both Windows 10 Professional as well as Office 2019 which covers full Microsoft terms and conditions for the purpose of using sysyprep.

Now that that is settled, back to my actual question.

Let me be clear because as I interpret your comment, you said you own a volume license for both Windows 10 Pro and Office 2019.  If you only own a single volume license for office, you are only able to create one image and deploy it to ONE computer.  Windows re-imaging rights allows you to create a reference image with the volume license for Windows and re-deploy to all machines you purchase with a pre-loaded Windows 10 Pro license.  HOWEVER, there is no volume license equivalent to Office 2019.  They are separate products with separate features.  Yes, they include Word, Excel, and PowerPoint, but they are different.  Professional Plus and Standard are the only perpetual licenses that are sold as volume licenses.  Professional Plus is NOT the same as Professional.  It really doesn't matter what version you have, if you don't have Standard or Professional Plus, you CANNOT, as the end user, include it in your customized image built using volume license media.

Office 2019 deployment is summarized here:
https://docs.microsoft.com/en-us/deployoffice/office2019/deploy

I'm sorry if I'm misinterpreting your question, however, two other experts acknowledged my post without further comment, so it would appear I'm not the only one misinterpreting, if that is indeed the case.

Gees sir, I asked a technical question and all you are answering with are licensing concerns, which there are absolutely no licensing concerns with what I am doing. Period. End of story. I thoroughly investigated the Office 2019 OEM licensing with both Dell and the Dell Microsoft Licensing group because this was the first time in our company history we were going to be purchasing Office OEM instead of Office VOL because of the substantial difference in cost.

My post is a technical question since I received 2 different answers from Dell support. I was hoping to get real world expert responses.

One answer I received from Dell support was that I had to first do the sysprep image to deploy to each workstation then do the Dell Digital download of Office 2019 OEM individually on each workstation. The other answer said I can do the Dell Digital download of Office 2019 OM on the first workstation and as long as I do not activate it then I can sysprep and deploy the image to each workstation and then just have to activate Office 2019 OEM.

Licensing is important because the question you are asking is how to do something that would violate licensing - how to do something with a version of the software that experienced professionals wouldn't do because it violates licensing.  You want an answer to a question we can't answer because we don't use the the products against the license agreement.

If you have the appropriate versions, I have given you a direct link to Microsoft documentation for deployment.  

Part of that substantial difference in cost is the RIGHTS you get with the license.  You pay more for the rights to re-image because, among other things, it saves on the cost of deployment and (it would seem to me) Microsoft want's a cut for giving you that right.  You can argue it as right or wrong, fair or not, but at the end of the day, that's what the volume license and the rights attached to each edition come down to.  Microsoft offering you greater capabilities for a greater price and lesser capabilities for a lesser price.  Capabilities aren't always technical... sometimes they are legal.

Good luck.

And I do get your frustration.  I'm sorry you were apparently mislead or perhaps misunderstood what was being sold and the rights involved.  Most folks who aren't experienced with imaging don't realize these limitations until it's too late.  And again, if I've misunderstood, I apologize, but your comments so far suggest to me I have not misunderstood.