I was going to write this question - but Denis pinged me on Discord - however I thought I would lob this into the list in case someone else hits the problem and is searching for it. (Maybe I should stick this in Calypso or Commander faq). My problem was that I had built a sub menu in Calypso and specified the order of the menu items as described in the docs. packageContextMenuActivation <classAnnotation> ^ CmdContextMenuActivation byItemOf: ClyExercismMenuGroup order: self contextMenuOrder for: ClyTaggedClassGroup asCalypsoItemContext However when I went to add some icons and change the ordering I was finding that my menu wasnât updating. There are 2 solutions (one better than the other). The brute force way is: CmdContextMenuActivation resetCache. The elegant way was to add an annotation to my menu ordering method contextMenuOrder <classAnnotationDependency> ^1 Tim By the way - to see what icons you can use in your menus, inspect: ThemeIcons current