diff --git a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java
index b8efd3fdfd9..08fcccbe4dc 100644
--- a/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java
+++ b/jetty-webapp/src/main/java/org/eclipse/jetty/webapp/WebInfConfiguration.java
@@ -785,8 +785,11 @@ public class WebInfConfiguration extends AbstractConfiguration
         }
         catch (Exception e)
         {
-            LOG.warn("Can't get resource for resourceBase",  e);
-            LOG.debug(e);
+            if (LOG.isDebugEnabled())
+            {
+                LOG.debug("Can't get resource base name", e);
+            }
+            canonicalName.append("-"); // empty resourceBaseName segment
         }
 
         //Context name
@@ -818,60 +821,50 @@ public class WebInfConfiguration extends AbstractConfiguration
         }
         catch (IOException e)
         {
-            LOG.ignore(e);
+            if (LOG.isDebugEnabled())
+            {
+                LOG.debug("Resource has no File reference: {}", resource);
+            }
         }
 
         // Use URI itself.
         URI uri = resource.getURI();
         if (uri == null)
         {
-            throw new RuntimeException("Unable to produce URI from resource: " + resource);
+            if (LOG.isDebugEnabled())
+            {
+                LOG.debug("Resource has no URI reference: {}", resource);
+            }
+            return "";
         }
+
         return getUriLastPathSegment(uri);
     }
 
     protected static String getUriLastPathSegment(URI uri)
     {
-        String path = uri.getPath();
-
-        if ("jar".equalsIgnoreCase(uri.getScheme()))
+        String ssp = uri.getSchemeSpecificPart();
+        // strip off deep jar:file: reference information
+        int idx = ssp.indexOf("!/");
+        if (idx != -1)
         {
-            String schemeSpecificPart = uri.getRawSchemeSpecificPart();
-            URI inner = URI.create(schemeSpecificPart);
-            if ("file".equalsIgnoreCase(inner.getScheme()))
-            {
-                path = inner.getRawPath();
-                int idx = path.lastIndexOf("!/");
-                if (idx >= 0)
-                {
-                    String pathInJar = path.substring(idx + 2);
-                    if (StringUtil.isNotBlank(pathInJar))
-                    {
-                        URI pathInJarUri = URI.create(pathInJar);
-                        return getUriLastPathSegment(pathInJarUri);
-                    }
-                    else
-                    {
-                        // Strip empty "!/"
-                        path = path.substring(0, idx);
-                    }
-                }
-                // if we reached here, we have "jar:file:" but no
-                // internal jar reference with "!/" present
-            }
-            else
-            {
-                // inner URI is not "file"
-                return getUriLastPathSegment(inner);
-            }
+            ssp = ssp.substring(0, idx);
         }
 
-        if (path.endsWith("/"))
-            path = path.substring(0, path.length() - 1);
-        // get just the last part which is the filename
-        int i = path.lastIndexOf("/");
+        // Strip off trailing '/' if present
+        if (ssp.endsWith("/"))
+        {
+            ssp = ssp.substring(0, ssp.length() - 1);
+        }
 
-        return path.substring(i + 1);
+        // Only interested in last segment
+        idx = ssp.lastIndexOf('/');
+        if (idx != -1)
+        {
+            ssp = ssp.substring(idx + 1);
+        }
+
+        return ssp;
     }
 
     protected List<Resource> findClassDirs(WebAppContext context)
diff --git a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebInfConfigurationTest.java b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebInfConfigurationTest.java
index 130de381851..28c1f5a0aa7 100644
--- a/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebInfConfigurationTest.java
+++ b/jetty-webapp/src/test/java/org/eclipse/jetty/webapp/WebInfConfigurationTest.java
@@ -158,7 +158,7 @@ public class WebInfConfigurationTest
         assertThat(WebInfConfiguration.getResourceBaseName(resource), is(expectedName));
     }
 
-    public static Stream<Arguments> baseResourceNames()
+    public static Stream<Arguments> fileBaseResourceNames()
     {
         return Stream.of(
             Arguments.of("test.war", "test.war"),
@@ -178,7 +178,7 @@ public class WebInfConfigurationTest
     }
 
     @ParameterizedTest
-    @MethodSource("baseResourceNames")
+    @MethodSource("fileBaseResourceNames")
     public void testPathGetResourceBaseName(String basePath, String expectedName) throws IOException
     {
         Path root = workDir.getPath();
@@ -198,15 +198,43 @@ public class WebInfConfigurationTest
         assertThat(WebInfConfiguration.getResourceBaseName(resource), is(expectedName));
     }
 
+    public static Stream<Arguments> fileUriBaseResourceNames()
+    {
+        return Stream.of(
+            Arguments.of("test.war", "test.war"),
+            Arguments.of("a/b/c/test.war", "test.war"),
+            Arguments.of("bar%2Fbaz/test.war", "test.war"),
+            Arguments.of("fizz buzz/test.war", "test.war"),
+            Arguments.of("another one/bites the dust/", "bites the dust"),
+            Arguments.of("another+one/bites+the+dust/", "bites+the+dust"),
+            Arguments.of("another%20one/bites%20the%20dust/", "bites%20the%20dust"),
+            Arguments.of("spanish/n\u00FAmero.war", "n\u00FAmero.war"),
+            Arguments.of("spanish/n%C3%BAmero.war", "n%C3%BAmero.war"),
+            Arguments.of("a/b!/", "b"),
+            Arguments.of("a/b!/c/", "b"),
+            Arguments.of("a/b!/c/d/", "b"),
+            Arguments.of("a/b%21/", "b%21")
+        );
+    }
+
     /**
      * Similar to testPathGetResourceBaseName, but with "file:" URIs
      */
     @ParameterizedTest
-    @MethodSource("baseResourceNames")
+    @MethodSource("fileUriBaseResourceNames")
     public void testFileUriGetUriLastPathSegment(String basePath, String expectedName) throws IOException
     {
         Path root = workDir.getPath();
         Path base = root.resolve(basePath);
+        if (basePath.endsWith("/"))
+        {
+            FS.ensureDirExists(base);
+        }
+        else
+        {
+            FS.ensureDirExists(base.getParent());
+            FS.touch(base);
+        }
         URI uri = base.toUri();
         if (OS.MAC.isCurrentOs())
         {
@@ -216,7 +244,7 @@ public class WebInfConfigurationTest
         assertThat(WebInfConfiguration.getUriLastPathSegment(uri), is(expectedName));
     }
 
-    public static Stream<Arguments> jarFileBaseResourceNames() throws URISyntaxException, IOException
+    public static Stream<Arguments> uriLastSegmentSource() throws URISyntaxException, IOException
     {
         Path testJar = MavenTestingUtils.getTestResourcePathFile(TEST_RESOURCE_JAR);
         URI uri = new URI("jar", testJar.toUri().toASCIIString(), null);
@@ -243,17 +271,7 @@ public class WebInfConfigurationTest
                     }
                     else
                     {
-                        String lastPathSegment = TEST_RESOURCE_JAR;
-                        if (path.getFileName() != null)
-                        {
-                            lastPathSegment = path.getFileName().toString();
-                        }
-                        // Strip last '/' from directory entries
-                        if (Files.isDirectory(path) && lastPathSegment.endsWith("/"))
-                        {
-                            lastPathSegment = lastPathSegment.substring(0, lastPathSegment.length() - 1);
-                        }
-                        arguments.add(Arguments.of(path.toUri(), lastPathSegment));
+                        arguments.add(Arguments.of(path.toUri(), TEST_RESOURCE_JAR));
                     }
                 });
             }
@@ -263,11 +281,11 @@ public class WebInfConfigurationTest
     }
 
     /**
-     * Tests of "jar:file:" based URIs
+     * Tests of URIs last segment, including "jar:file:" based URIs.
      */
     @ParameterizedTest
-    @MethodSource("jarFileBaseResourceNames")
-    public void testJarFileUriGetUriLastPathSegment(URI uri, String expectedName) throws IOException
+    @MethodSource("uriLastSegmentSource")
+    public void testGetUriLastPathSegment(URI uri, String expectedName) throws IOException
     {
         assertThat(WebInfConfiguration.getUriLastPathSegment(uri), is(expectedName));
     }