Is it possible for the "same" file to be attached to multiple work item?

2 answers

You do not have to attach it. You can reference it in the description or comment or Summary.
Example File was attached to a "Work Item 1502" and it was given an ID 2
You can reference it in another "Work Item 1503" in the comment or description as
example adding a comment to WI

Adding it to another WorkItem

Comments

Thanks for your reply. But as they say, this is a correct answer, but not the correct answer I want :-).
Unfortunately, the work items are not always for human consumption and the files (generic instructions, generic config etc) attachments must be present. The scripts etc will be "downloading" the attachments along with other artefacts like build results to machines that do not have RTC clients installed

Can you be specific ?
How you are reading the attachments from the scripts from a single Work Item?