Hi Connor - We have had similar issues in the past, so we always make sure to have AMP engine on (I was in the habit of turning it off because of the issues it would to cause. Have since reverted to trying to use it for all Workflows)
We had AMP engine enabled. Essentially the template tool is not reading in the PDF or JSON (for annotations/bounds) when it is on server. We troubleshooted using the normal "does server have access to those files or are the files in some way embedded in the workflow" and still no dice.
What I ended up doing was actually editing the "annotations [bounds]" within the XML editor of the imagine template tool. I took the text for the "bounds" property from the JSON file and pasted it directly into the XML of the template tool. It looks like when pushing to server, it was trunkating some of the bounds, or not accessing the full file, or something along those lines.
In additional, I changed dependencies to absolute (was on UNC).
Not sure which one exactly fixed it, but it looks like it is working properly now.
It should be noted that we had several image template tools that the user selects via drop down - the first image template always worked on server, but the following did not. So, our issue was caused by multiple Image Template tools - meaning it might have been different from yours but sharing this none the less in case it is useful to anyone else.
