Installing a cached item policy failing

Can you elaborate on what you mean by "hung up"? The policy is getting stuck or something?
How are you doing the older Office removal part? Script? Uninstall with package? What order are the processes set up in the policy? I assume the removal is first, then the install cached, but have you double checked to make sure they are going in that exact order?

Sure thing. Here is the error I am seeing

Actions from policy log: Executing Policy Office 365 Install Cached... Getting package details from https://jss:8443/... Uninstalling... Looking for Applications... Deleting files... Uninstalled Office020513.dmg. Error: The package (3M Office 365 Office Installer.pkg) could not be found. Error: The package (Lync Installer.pkg) could not be found. Error: The package (Office 2011 14.4.4 Update.pkg) could not be found. Relaunching dock(s)... Running Recon... Retrieving inventory preferences from https://jss:8443/... Locating package receipts... Locating accounts... Searching path: /Users Locating software updates... Locating plugins... Locating printers... Searching path: /Applications

The complete policy log is available in the JSS at:

I am removing office by indexing the package in casper admin used to install office and using the uninstall function. I will double check the priority order, but I am quite certain they are correct.

Screenshots:
https://www.dropbox.com/s/np1ondnjmpbwozz/Screenshot%202014-10-15%2012.05.45.png?dl=0
https://www.dropbox.com/s/imd6p3y7ksyq8bc/Screenshot%202014-10-15%2012.05.52.png?dl=0
https://www.dropbox.com/s/gkqkn2pqiajt0aq/Screenshot%202014-10-15%2012.06.13.png?dl=0

Old office: Priority 5
New office: Priority 6
Lync: Priorirty 10
Update: Priority 11

Thanks for your help!

Hmm, OK. So this line the log is throwing me a little, and it could simply be because I rarely ever do uninstalls using indexed packages. There are pros and cons to the approach.

Uninstalled Office020513.dmg

What is the DMG its uninstalling there? Or is that simply how it appears when you use a dmg as the uninstall package? Again, don't do it often enough to be familiar with it.

I can't be sure, but I'm wondering if somehow the uninstall is also removing the cached packages and then it fails? If you're certain the packages are correctly cached in /Library/Application Support/Waiting Room/ then it sounds as if something is blowing them away. Maybe its the uninstall, but that actually shouldn't happen.

I would consider using a scripted process to do the uninstall. I have used a script posted by @talkingmoose on his blog, which you can find here.
http://www.officeformachelp.com/office/install/remove-office/
This script always does the trick in uninstalling Office 2011 completely from a Mac. The only thing is, I've never used it with an Office365 installation. it was obviously written just for plain ol' Office 2011, but it probably works the same. I would give that a try maybe.

Thank you for that. It appears that while the policy caching the installers seem to execute cleanly, when I check the waiting room directory, it is empty. blah!

Ah, so they never actually make it into Waiting Room then? Well, that would explain the error :) But it doesn't explain why its not working. No errors to speak of in the policy log?

Edit: You don't happen to have another policy that periodically clears out the Waiting Room folder do you? We have something like that that runs once a week and so had to stop using any caching using the built in policy function since there was no guarantee the Waiting Room purge wouldn't occur soon after it actually cached packages.

I don't and I think I may have jumped the gun a bit. I can't verify yet whether Waiting Room is clear or not. Will keep you posted and thank you again.