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My problem is that the file uploader I'm working with will only allow a zip file with a size of 10mb or less. Unfortunately, I have thousands of files that need to be processed and I do this by uploading multiple 10mb zip files, manually.

How would one go about doing so automatically?

Things to consider:
- (software wise) If there is no way of knowing what the compressed size is going to be before
- hand maybe there would be a way of selecting how many files are allowed to be in each zip file?
- Maybe similar to these questions but on Windows? Compress a folder into multiple zip files, http://apple.stackexchange.com/questions/12371/how-can-i-compress-a-folder-into-multiple-zip-filess

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You could easily use power she'll. If you don't have this answered, when I get time tonight or tomorrow I'll write one for you. – Tim Dec 30 '15 at 19:38

7Zip should be able to do this. Here is a detailed tutorial using it.

Use the split to volumes option.

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Yep, any decent archiver can create a single huge archive that's split into 10MB parts. All parts will of course be required to get the original archive back, although individual files may be retrieved if all the parts for them are available. – Karan Mar 7 '13 at 18:54
    
Splitting an archive is not something I can do. I need to split multiple unzipped files to multiple zipped files with the ability to access each one independently. – Shaz Mar 7 '13 at 19:04
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@Shaz: WinRAR can show you a rough estimate of the compression ratio for selected files, but it would be extremely difficult to automate this (it would need to be executed repeatedly with different sets of files selected till the estimate is around 10 MB, then those files would need to be compressed, plus a list would have to be maintained so already compressed files aren't re-compressed, and the entire process would have to be repeated till all files are compressed). A custom program might be the answer. – Karan Mar 8 '13 at 3:26
    
PKZip 2.04g had no support for splitting, but Arj and Rar did. I think Info-Zip 3.0 and Unzip 6.0 do too and I'm not surprised that 7-zip does, but I think different zippers may have different compatibility for split archives. Since you rejected split archives, I have fully read Karan's comment and endorse it. The best way for a program to get a decently likely/reliable compression estimate is to do at least most of the math/work required to compress; after that, it usually makes sense to just write results to disk. – TOOGAM Apr 9 at 2:45

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