diff --git a/core/src/main/java/hudson/Functions.java b/core/src/main/java/hudson/Functions.java
index 04ba6a3075..c60e1140e5 100644
--- a/core/src/main/java/hudson/Functions.java
+++ b/core/src/main/java/hudson/Functions.java
@@ -1830,7 +1830,7 @@ public class Functions {
     public static String breakableString(final String plain) {
 
         return plain.replaceAll("([\\p{Punct}&&[^;]]+\\w)", "<wbr>$1")
-                .replaceAll("([^\\p{Punct}\\s-]{10})(?=[^\\p{Punct}\\s-]{3})", "$1<wbr>")
+                .replaceAll("([^\\p{Punct}\\s-]{20})(?=[^\\p{Punct}\\s-]{10})", "$1<wbr>")
         ;
     }
 
diff --git a/core/src/test/java/hudson/FunctionsTest.java b/core/src/test/java/hudson/FunctionsTest.java
index 6bc0b11664..f0e5213900 100644
--- a/core/src/test/java/hudson/FunctionsTest.java
+++ b/core/src/test/java/hudson/FunctionsTest.java
@@ -309,7 +309,9 @@ public class FunctionsTest {
 
         assertBrokenAs("Hello world!", "Hello world!");
         assertBrokenAs("Hello-world!", "Hello", "-world!");
-        assertBrokenAs("ALongStringThatCanNotBeBrokenByDefault", "ALongStrin", "gThatCanNo", "tBeBrokenB", "yDefault");
+        assertBrokenAs("ALongStringThatCanNotBeBrokenByDefaultAndNeedsToUseTheBreakableElement",
+                "ALongStringThatCanNo", "tBeBrokenByDefaultAn", "dNeedsToUseTheBreaka", "bleElement");
+        assertBrokenAs("DontBreakShortStringBefore-Hyphen", "DontBreakShortStringBefore", "-Hyphen");
         assertBrokenAs("jenkins_main_trunk", "jenkins", "_main", "_trunk");
 
         assertBrokenAs("&lt;&lt;&lt;&lt;&lt;", "", "&lt;", "&lt;", "&lt;", "&lt;", "&lt;");
@@ -319,7 +321,7 @@ public class FunctionsTest {
         assertBrokenAs("A;String>Full]Of)Weird}Punctuation", "A;String", ">Full", "]Of", ")Weird", "}Punctuation");
         assertBrokenAs("&lt;&lt;a&lt;bc&lt;def&lt;ghi&lt;", "", "&lt;", "&lt;a", "&lt;bc", "&lt;def", "&lt;ghi", "&lt;");
         assertBrokenAs("H,e.l/l:o=w_o+|d", "H", ",e", ".l", "/l", ":o", "=w", "_o", "+|d");
-        assertBrokenAs("a¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷ", "a¶‱ﻷa¶‱ﻷa¶", "‱ﻷa¶‱ﻷa¶‱ﻷ", "a¶‱ﻷa¶‱ﻷa¶‱ﻷ");
+        assertBrokenAs("a¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷ", "a¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷa¶‱ﻷ", "a¶‱ﻷa¶‱ﻷa¶‱ﻷ");
     }
 
     private void assertBrokenAs(String plain, String... chunks) {