Developed a robust S3 upload reliability enhancement for the BerriAI/litellm repository, focusing on data integrity during high-throughput operations. The work centered on implementing an exponential backoff retry mechanism in Python for both synchronous and asynchronous S3 upload functions, addressing transient 500 and 503 errors that previously caused frequent data loss. Integrated AWS S3 and backend development skills to ensure the retry logic attempted uploads up to three times with increasing delays, while targeted unit tests validated correct behavior for various error scenarios. Enhanced observability was achieved through detailed logging, resulting in improved system resilience and reduced production fragility.