iPhone Content Transfer Recommendations

Wow so many great responses to this post. :-) I have a similar question. Apple's tools like Quick Start and Direct Transfer work great and are well documented. I'd like to know what are the "gotchas" for using that migration path in an enterprise environment with MDM. For example, the common scenario where end user wants to migrate from an old (non-MDM) iPhone to a new (ADE/DEP enrolled) iPhone. Is this supposed to work? What are the caveats, if any?

Some evidence that Direct Transfer (Device to Device Migration) will not work with MDM devices involved: https://developer.apple.com/forums/thread/123433

iCloud has always worked fine for me for DEP>DEP and nonDEP>DEP device enrollments. My main issue is users not remembering their Apple IDs and/or generally knowing how they work, or once in a while, using their personal iCloud that only has 5 GB storage so it fills up fast between two phones. So usually what I do is make a backup with configurator and restore it to the new phone. This also seems to handle DEP>DEP and nonDEP>DEP migrations without issue. It's not perfect because their data is not being backed up regularly, but it works well enough for my situation. I had planned to get managed Apple IDs tied to our AD source to give them an easy way to have iCloud storage without needing another password but turns out lots of people already used their work email to make regular Apple IDs and the thought of trying to institute that change with everything else going on this year was a little overwhelming.

iCloud backups are a poor option when Apple only provides 5GB iCloud space by default. Most of our users don't pay for iCloud storage. The Device-to-Device transfer introduced with iOS 12 works great in the consumer realm. It's been problematic when attempting nonDEP->DEP device, in my experience.

Did you ever figure out if this works? the device to device method. I know it works great on an unmanaged iphone. How are people doing this a year later?

EDIT: i figured out what i am doing wrong. I had restricted the following items in prestage:
- apple id and icloud
- apps and data
- transfer data

The transfer data i think is the key here. I did the others due to how we are using staff phones.

does this resolve the direct transfer?

I had a similar issue previously and direct transfer works when you use the setup new phone for transfer option in the reset page.
This is a super old post but wanted to give a current update on this.

I have noticed on occasion it will has its issues, some devices the option is grayed out stating the device or apple ID is managed and doesn't allow so I have to physically backup on my Mac.
But overall it works great, if it at times doesn't begin to back it up, create a normal backup, delete it, then try again and should work.