Bizarre Document Submissions: Tales from the Trenches of Client Communication

In the world of freelance work and client collaborations, the methods of document submission can sometimes be as unique as the individuals behind them. I recently encountered a particularly peculiar experience that got me thinking: What are some of the strangest ways professionals have received documents from clients?

Let me share my story: I once had a client who sent me a photo of a PDF displayed on their iPad—taken with a Samsung phone—via email. Yes, you read that correctly. Instead of sending me the actual document, they decided that snapping a picture of the screen was the most efficient approach. As a result, we found ourselves having to manually process that invoice, which was not exactly ideal.

Now I’m reaching out to my fellow professionals: What’s the most outlandish or bizarre document submission you’ve encountered? Have you received handwritten notes that were nearly illegible? Or perhaps a scan that was upside down? Maybe a file named “Image(345).jpg” with no context whatsoever?

I’m gathering stories from the community to shed light on the chaos we often face in document handling. This is not a pitch for any service—just an inquiry to reassure myself (and others) that we are not alone in dealing with these amusingly frustrating scenarios. Share your experiences in the comments below; let’s commiserate and maybe even chuckle at the quirks of client communication!