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Cultural background influences aesthetic web design preferences, and aesthetic design impacts accessible design. However, limited research has focused on this intersection of cultural background and accessible web design. With the majority of HCI and design resources originating from the Global North, we investigated the conflicts experienced due to the cultural background of digital designers from the Global South and current web accessibility guidelines. We conducted a design activity and interview study with 10 designers from five countries in the Global South to identify how current web accessibility guidelines conflict with our participants’ cultural design preferences. We found there are specific cultural challenges encountered in accessible web design, both at the design level (e.g., typography and color scheme) and within broader societal contexts (e.g., designer-client interactions). Our paper also offers suggestions from our participants to make the accessible design process more culturally inclusive by improving the web accessibility resources to become culturally customized and engaging more cultural perspectives in accessibility research and education.