We did purchase the cloudberry explorer pro license for the native multipart upload capability, but we wanted to automate it. I believe based on their documentation that the old chunk method is deprecated in favor of their new multi-part functionality. We wound up testing the options listed in the powershell documentation. Those options are as follows:
Set-CloudOption -UseChunks -ChunkSizeKB
"Defines a size of chunk in KB; files larger than a chunk will be divided into chunks."
We verified that this was successfully uploading files beyond the 5GB restriction to our S3 bucket. I attempted to get a response from Cloudberry as to whether this was the old Chunking method or the new Multi-Part method, but I was unable to get a straight answer. They confirmed that because we were using pro, this powershell option was supported, but they failed to confirm which option the powershell command was using.
From what I can tell it appears that Cloudberry's legacy chunking mechanism would actually just break the file into individual files and thus would appear in S3 as multiple files. The Chunk Transparency mechanism in Cloudberry Explorer would allow the multiple chunks to appear as a single file in the Cloudberry Explorer GUI only. Since I can see the file as a single file on the S3 side, I'm assuming that the powershell option uses the new Multi-Part functionality and not the legacy Chunking functionality. Again I was not able to confirm this through Cloudberry so it's speculation on my part.
However, I can confirm that using the powershell options above will get you around the 5GB upload limit when using powershell.