I would like our work items to automatically get a copy of the check in notes appended at each check in.
Whether this is in the "History" tab or on another tab like, "Check In Notes" is immaterial. It just makes sense that this information would filter up to the PM without having to go through each Changeset in the link.
Alternatively, you could just use the Comments piece of the changeset link to hold the check in notes. Right now they currently say "Source control changeset 3242" which is a bit obvious from the linktype (Changeset) and description (Changeset 3242)....
Can I change the behavior in some way or would this require a new release of TFS

Adding Check In comments to Work Item history
Mable
Thanks, but the main problem with using a check-in policy is that the policy is fully executed when they click on the Check In policy button and again if they commit it. Which leaves two comments. Also, if they cancel the dialog then I have no way of undoing the note.
Oh well.
Abe1816
The Changeset is not a type of work items. There has not been an easy and reliable way to change the behavior of it. Sorry for the inconvenience. Maybe in the new release of TFS it will improve the behavior.
Thank you for using the TFS.
Balavenkatesh