Before bundling, Base.css was included as "~/Content/themes/base/Base.css" and image path was therefore "~/Content/Images/external.png". Bundling shortens URL
That makes image path to be "~/Content/../../Images/external.png" which is obviously wrong. The easiest solution is probably to artificially extend the bundled path to match previous folder structure, e.g.
Some of the stylesheets include relative references to the static files, e.g. in \Content\themes\base\Base.css
Before bundling, Base.css was included as "~/Content/themes/base/Base.css" and image path was therefore "~/Content/Images/external.png". Bundling shortens URL
That makes image path to be "~/Content/../../Images/external.png" which is obviously wrong. The easiest solution is probably to artificially extend the bundled path to match previous folder structure, e.g.