diff --git a/jetty-util/src/main/java/org/eclipse/jetty/util/URIUtil.java b/jetty-util/src/main/java/org/eclipse/jetty/util/URIUtil.java
index 7f912103ea7..b0c75a0f795 100644
--- a/jetty-util/src/main/java/org/eclipse/jetty/util/URIUtil.java
+++ b/jetty-util/src/main/java/org/eclipse/jetty/util/URIUtil.java
@@ -20,6 +20,11 @@ package org.eclipse.jetty.util;
 
 import java.nio.charset.Charset;
 import java.nio.charset.StandardCharsets;
+import java.util.Collections;
+import java.util.LinkedList;
+import java.util.List;
+import java.util.ListIterator;
+import java.util.regex.Pattern;
 
 import org.eclipse.jetty.util.Utf8Appendable.NotUtf8Exception;
 import org.eclipse.jetty.util.log.Log;
@@ -49,6 +54,7 @@ public class URIUtil
     public static final String HTTP_COLON="http:";
     public static final String HTTPS="https";
     public static final String HTTPS_COLON="https:";
+    private static final Pattern __PATH_SPLIT = Pattern.compile("(?<=\\/)");
 
     // Use UTF-8 as per http://www.w3.org/TR/html40/appendix/notes.html#non-ascii-chars
     public static final Charset __CHARSET=StandardCharsets.UTF_8 ;
@@ -503,130 +509,40 @@ public class URIUtil
      */
     public static String canonicalPath(String path)
     {
-        if (path==null || path.length()==0)
+        if (path == null || path.isEmpty() || !path.contains("."))
             return path;
 
-        int end=path.length();
-        int start = path.lastIndexOf('/', end);
+        if(path.startsWith("/.."))
+            return null;
 
-    search:
-        while (end>0)
+        List<String> directories = new LinkedList<>();
+        Collections.addAll(directories, __PATH_SPLIT.split(path));
+
+        for(ListIterator<String> iterator = directories.listIterator(); iterator.hasNext();)
         {
-            switch(end-start)
-            {
-              case 2: // possible single dot
-                  if (path.charAt(start+1)!='.')
-                      break;
-                  break search;
-              case 3: // possible double dot
-                  if (path.charAt(start+1)!='.' || path.charAt(start+2)!='.')
-                      break;
-                  break search;
+            switch (iterator.next()) {
+                case "./":
+                case ".":
+                    if (iterator.hasNext() && directories.get(iterator.nextIndex()).equals("/"))
+                        break;
+
+                    iterator.remove();
+                    break;
+                case "../":
+                case "..":
+                    if(iterator.previousIndex() == 0)
+                        return null;
+
+                    iterator.remove();
+                    if(iterator.previous().equals("/") && iterator.nextIndex() == 0)
+                        return null;
+
+                    iterator.remove();
+                    break;
             }
-            
-            end=start;
-            start=path.lastIndexOf('/',end-1);
         }
 
-        // If we have checked the entire string
-        if (start>=end)
-            return path;
-        
-        StringBuilder buf = new StringBuilder(path);
-        int delStart=-1;
-        int delEnd=-1;
-        int skip=0;
-        
-        while (end>0)
-        {
-            switch(end-start)
-            {       
-              case 2: // possible single dot
-                  if (buf.charAt(start+1)!='.')
-                  {
-                      if (skip>0 && --skip==0)
-                      {   
-                          delStart=start>=0?start:0;
-                          if(delStart>0 && delEnd==buf.length() && buf.charAt(delEnd-1)=='.')
-                              delStart++;
-                      }
-                      break;
-                  }
-                  
-                  if(start<0 && buf.length()>2 && buf.charAt(1)=='/' && buf.charAt(2)=='/')
-                      break;
-                  
-                  if(delEnd<0)
-                      delEnd=end;
-                  delStart=start;
-                  if (delStart<0 || delStart==0&&buf.charAt(delStart)=='/')
-                  {
-                      delStart++;
-                      if (delEnd<buf.length() && buf.charAt(delEnd)=='/')
-                          delEnd++;
-                      break;
-                  }
-                  if (end==buf.length())
-                      delStart++;
-                  
-                  end=start--;
-                  while (start>=0 && buf.charAt(start)!='/')
-                      start--;
-                  continue;
-                  
-              case 3: // possible double dot
-                  if (buf.charAt(start+1)!='.' || buf.charAt(start+2)!='.')
-                  {
-                      if (skip>0 && --skip==0)
-                      {   delStart=start>=0?start:0;
-                          if(delStart>0 && delEnd==buf.length() && buf.charAt(delEnd-1)=='.')
-                              delStart++;
-                      }
-                      break;
-                  }
-                  
-                  delStart=start;
-                  if (delEnd<0)
-                      delEnd=end;
-
-                  skip++;
-                  end=start--;
-                  while (start>=0 && buf.charAt(start)!='/')
-                      start--;
-                  continue;
-
-              default:
-                  if (skip>0 && --skip==0)
-                  {
-                      delStart=start>=0?start:0;
-                      if(delEnd==buf.length() && buf.charAt(delEnd-1)=='.')
-                          delStart++;
-                  }
-            }     
-            
-            // Do the delete
-            if (skip<=0 && delStart>=0 && delEnd>=delStart)
-            {  
-                buf.delete(delStart,delEnd);
-                delStart=delEnd=-1;
-                if (skip>0)
-                    delEnd=end;
-            }
-            
-            end=start--;
-            while (start>=0 && buf.charAt(start)!='/')
-                start--;
-        }      
-
-        // Too many ..
-        if (skip>0)
-            return null;
-        
-        // Do the delete
-        if (delEnd>=0)
-            buf.delete(delStart,delEnd);
-
-        return buf.toString();
+        return String.join("", directories);
     }
 
     /* ------------------------------------------------------------ */