diff --git a/core/src/main/java/hudson/Functions.java b/core/src/main/java/hudson/Functions.java
index a57bd94306..c92e5fe516 100644
--- a/core/src/main/java/hudson/Functions.java
+++ b/core/src/main/java/hudson/Functions.java
@@ -2383,7 +2383,9 @@ public class Functions {
                 iconGuess = "/" + iconGuess;
             }
             if (iconGuess.startsWith(rootURL)) {
-                iconGuess = iconGuess.substring(rootURL.length());
+                if ((!rootURL.equals("/images") && !rootURL.equals("/plugin")) || iconGuess.startsWith(rootURL + rootURL)) {
+                    iconGuess = iconGuess.substring(rootURL.length());
+                }
             }
             iconSource = rootURL + (iconGuess.startsWith("/images/") || iconGuess.startsWith("/plugin/") ? getResourcePath() : "") + iconGuess;
         }
diff --git a/core/src/test/java/hudson/FunctionsTest.java b/core/src/test/java/hudson/FunctionsTest.java
index 30d6d31c97..f9b42f97ef 100644
--- a/core/src/test/java/hudson/FunctionsTest.java
+++ b/core/src/test/java/hudson/FunctionsTest.java
@@ -682,10 +682,15 @@ public class FunctionsTest {
         Jenkins.RESOURCE_PATH = "/static/12345678";
         assertEquals("/jenkins/static/12345678/images/48x48/green.gif", Functions.guessIcon("jenkins/images/48x48/green.gif", "/jenkins"));
         assertEquals("/jenkins/static/12345678/images/48x48/green.gif", Functions.guessIcon("/jenkins/images/48x48/green.gif", "/jenkins"));
+        assertEquals("/static/12345678/images/48x48/green.gif", Functions.guessIcon("images/48x48/green.gif", ""));
         assertEquals("/jenkins/static/12345678/images/48x48/green.gif", Functions.guessIcon("images/48x48/green.gif", "/jenkins"));
         assertEquals("/jenkins/static/12345678/images/48x48/green.gif", Functions.guessIcon("/images/48x48/green.gif", "/jenkins"));
+        assertEquals("/images/static/12345678/images/48x48/green.gif", Functions.guessIcon("/images/48x48/green.gif", "/images"));
+        assertEquals("/static/12345678/plugin/myartifactId/images/48x48/green.gif", Functions.guessIcon("/plugin/myartifactId/images/48x48/green.gif", ""));
         assertEquals("/jenkins/static/12345678/plugin/myartifactId/images/48x48/green.gif", Functions.guessIcon("/plugin/myartifactId/images/48x48/green.gif", "/jenkins"));
         assertEquals("/jenkins/static/12345678/plugin/myartifactId/images/48x48/green.gif", Functions.guessIcon("/jenkins/plugin/myartifactId/images/48x48/green.gif", "/jenkins"));
+        assertEquals("/plugin/static/12345678/plugin/myartifactId/images/48x48/green.gif", Functions.guessIcon("/plugin/myartifactId/images/48x48/green.gif", "/plugin"));
+        assertEquals("/plugin/static/12345678/plugin/myartifactId/images/48x48/green.gif", Functions.guessIcon("/plugin/plugin/myartifactId/images/48x48/green.gif", "/plugin"));
         assertEquals("http://acme.com/icon.svg", Functions.guessIcon("http://acme.com/icon.svg", "/jenkins"));
         assertEquals("https://acme.com/icon.svg", Functions.guessIcon("https://acme.com/icon.svg", "/jenkins"));
     }