Retention Policy or archival issues

Retention Policy or archival issues

To start with for investigation

1.There are two timer job services in Sharepoint 2010 ( it looks the same on 2013 as well) so ... "Information management policy" and "Expiration policy". check if these Job are working as desired for the web application. I understand it works partially on some instances. But I don't know if it is on the same webapp level.

2. Next can you check if these documents are checked-out to some one on the team or to a person who has left the firm which is very common sometime User Profile service may give you tickle by not syncing as desired.
3. If you have custom content type for which the the document is saved. then if the same content type exist on the destination folder ( drop off lib) where document to be moved.

I had a situation when the documents where located inside a folder (leaf) inside document library. Move of document expected a same folder on destination which was weird. But after changing folder name which had '(' symbol it worked.

I have also seen some instances of permissions to the folder for the timer job but, I did not have that experience.

If Move to recycle bin is working but Transfer isn't, I'm assuming your destination site is the same as the source. If so, this is not going to work because according to Microsoft support

It was as per design. If you try to move documents to a different location using Retention policy, you have to move it a library in a different site collection. Preferably ‘Records center‘ site collection. Main idea of Microsoft is to have one Archival or Records center site collection for the whole organization.

So, if you are trying to move documents after expiration to a library in same site or site collection, you can use a workaround to start a workflow on expiration date which moves the document to archival library.