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SAP is the market leader in enterprise software offering an end-to-end suite of applications and services to enable their customers worldwide to operate their business. Especially, retail customers of SAP deal with millions of sales transactions for their day-to-day business. Transactions are created during retail sales at the point of sale (POS) terminals and then sent to some central servers for validations and other business operations. A considerable proportion of the retail transactions may have inconsistencies due to many technical and human errors. SAP provides an automated process for error detection but still requires a manual process by dedicated employees using workbench software for correction. However, manual corrections of these errors are time-consuming, labor-intensive, and may lead to further errors due to incorrect modifications. This is not only a performance overhead on the customers' business workflow but it also incurs high operational costs. Thus, automated detection and correction of transaction errors are very important regarding their potential business values and the improvement in the business workflow. In this paper, we present an industrial case study where we apply machine learning (ML) to automatically detect transaction errors and propose corrections. We identify and discuss the challenges that we faced during this collaborative research and development project, from three distinct perspectives: Software Engineering, Machine Learning, and industry-academia collaboration. We report on our experience and insights from the project with guidelines for the identified challenges. We believe that our findings and recommendations can help researchers and practitioners embarking into similar endeavors., Comment: 21 pages, 5 figures