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So I have an import CSV (http://www.sharecsv.com/s/5565cf6cf17e0a2cfce2e9eaf50f8023/compiledBundle.csv). I have a few simple products that have a LOT of custom options. When importing some of the custom options will upload to the simple product and others won't. We will reset the database and do it again and this time DIFFERENT custom options will make it through. I can only think that the importer is having issues with how many options some of the simple products have.

Please refrain from giving me the "Have you tried Magmi" answer as it is not an option for multiple reasons that I will not go into here.

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This looks like the problem described in https://github.com/avstudnitz/AvS_FastSimpleImport/issues/69:

the import is split into batches of rows. If the split happens inside rows belonging to one product, part of the data might not be imported.

You should try to apply the patch given there. Direct link to the patch: https://gist.github.com/paales/7934644.

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