The raster image status icons of jobs on the dashboard are expected to display correctly. The actual behavior is icons being missing because the image URLs are malformed, containing the context path twice (/jenkins/jenkins/ on the following screenshot)

Functions.tryGetIconPath() appends the context path to the URL https://github.com/jenkinsci/jenkins/blob/master/core/src/main/java/hudson/Functions.java#L2380
but before that, StatusIcon.getImageOf() will have already appended it for StockStatusIcon and every other extension of StatusIcon that implements that method similarly, resulting in the malformed URL where the context path repeats twice. https://github.com/jenkinsci/jenkins/blob/20e34cb942a85fe1b55bb193ef3378c2eeb82098/core/src/main/java/hudson/model/StockStatusIcon.java#L31-L36