In the modern era of social media, users frequently promote their acts of generosity. Included in these acts of generosity are tips to restaurant servers that exceed customary amounts. Due to the extraordinary amounts of the transfers, the proper tax treatment as a “gift” or a “tip” is called into question. In Commissioner v. Duberstein, the Supreme Court addressed gifts versus taxable transfers but did not provide a clear test for taxpayers. In the sixty years since Duberstein, Congress has yet to address the call of Duberstein to create an appropriate test for gift treatment. In this paper, we analyze prior law on gifts and tips. Next, we apply the law to scenarios based on current events. Finally, we recommend that Congress address transfers where the appropriate treatment as a "gift" or a "tip" is in question.