The short answer is, "it depends". The only hard cap we have right now on file size is 5GB.
However, as file size increases the number of things that could go wrong also increases. For example, most Wrk Actions have a 5 minute timeout. If a file is so large that it takes more than 5 minutes to download this could result in errors.
There are a number of other things that could go wrong depending on how and where you are passing around large files. all that being said, we should be able to increase timeouts or make fixes that are needed in order to support the files of the size you need. Please let me know if you have a specific job/action that ends up causing problems.