Simon Tatham’s blog post explores the evolution of the iconic PuTTY logo used since the late 1990s and the challenges faced in designing various tool icons like PSCP, PSFTP, Pageant, and PuTTYgen. Tatham discusses his initial hand-drawn approach, the later transition to a scripted method for icon creation in 2007 due to changing display sizes, and the unexpected popularity of the quirky Pageant icon featuring a computer wearing a hat. He also delves into the introduction of icons for the Linux pterm tool, showcasing the intersection of technical and creative considerations in icon design.
https://www.chiark.greenend.org.uk/~sgtatham/quasiblog/putty-icons/