diff --git a/src/jdk.httpserver/share/classes/com/sun/net/httpserver/HttpServer.java b/src/jdk.httpserver/share/classes/com/sun/net/httpserver/HttpServer.java
index 67ac9e98e10..fb10ecb0755 100644
--- a/src/jdk.httpserver/share/classes/com/sun/net/httpserver/HttpServer.java
+++ b/src/jdk.httpserver/share/classes/com/sun/net/httpserver/HttpServer.java
@@ -284,8 +284,8 @@ public abstract class HttpServer {
      * then some implementations may use <em>string prefix matching</em> where
      * this context path matches request paths {@code /foo},
      * {@code /foo/bar}, or {@code /foobar}. Others may use <em>path prefix
-     * matching</em> where {@code /foo} matches only request paths
-     * {@code /foo} and {@code /foo/bar}, but not {@code /foobar}.
+     * matching</em> where {@code /foo} matches request paths {@code /foo} and
+     * {@code /foo/bar}, but not {@code /foobar}.
      *
      * @implNote
      * By default, the JDK built-in implementation uses path prefix matching.
diff --git a/src/jdk.httpserver/share/classes/module-info.java b/src/jdk.httpserver/share/classes/module-info.java
index 8f04cc4c7ce..bff221a920e 100644
--- a/src/jdk.httpserver/share/classes/module-info.java
+++ b/src/jdk.httpserver/share/classes/module-info.java
@@ -107,7 +107,7 @@ import com.sun.net.httpserver.*;
  * {@code pathPrefix})<br/>
  *
  * The path matching scheme used to route requests to context handlers.
- * Following list of values are allowed by this property.</p>
+ * The property can be configured with one of the following values:</p>
  *
  * <blockquote>
  * <dl>
@@ -117,7 +117,7 @@ import com.sun.net.httpserver.*;
  * would match request paths {@code /foo}, {@code /foo/}, and {@code /foo/bar},
  * but not {@code /foobar}.</dd>
  * <dt>{@code stringPrefix}</dt>
- * <dd>Request path string must begin with the context path string. For
+ * <dd>The request path string must begin with the context path string. For
  * instance, the context path {@code /foo} would match request paths
  * {@code /foo}, {@code /foo/}, {@code /foo/bar}, and {@code /foobar}.
  * </dd>
diff --git a/src/jdk.httpserver/share/classes/sun/net/httpserver/ContextList.java b/src/jdk.httpserver/share/classes/sun/net/httpserver/ContextList.java
index 935416c81b7..6393ca34798 100644
--- a/src/jdk.httpserver/share/classes/sun/net/httpserver/ContextList.java
+++ b/src/jdk.httpserver/share/classes/sun/net/httpserver/ContextList.java
@@ -40,6 +40,8 @@ class ContextList {
         // expects the protocol to be lower-cased using ROOT locale, hence:
         assert ctx.getProtocol().equals(ctx.getProtocol().toLowerCase(Locale.ROOT));
         assert ctx.getPath() != null;
+        // `ContextPathMatcher` expects context paths to be non-empty:
+        assert !ctx.getPath().isEmpty();
         if (contains(ctx)) {
             throw new IllegalArgumentException("cannot add context to list");
         }
@@ -199,10 +201,19 @@ class ContextList {
                 }
 
                 // Is it a path-prefix match?
-                if (contextPath.charAt(contextPathLength - 1) == '/'
-                        || requestPath.charAt(contextPathLength) == '/') {
-                    return true;
-                }
+                assert contextPathLength > 0;
+                return
+                        // Case 1: The request path starts with the context
+                        // path, but the context path has an extra path
+                        // separator suffix. For instance, the context path is
+                        // `/foo/` and the request path is `/foo/bar`.
+                        contextPath.charAt(contextPathLength - 1) == '/' ||
+                                // Case 2: The request path starts with the
+                                // context path, but the request path has an
+                                // extra path separator suffix. For instance,
+                                // context path is `/foo` and the request path
+                                // is `/foo/` or `/foo/bar`.
+                                requestPath.charAt(contextPathLength) == '/';
 
             }
 
diff --git a/test/jdk/com/sun/net/httpserver/ContextPathMatcherPathPrefixTest.java b/test/jdk/com/sun/net/httpserver/ContextPathMatcherPathPrefixTest.java
index 20b4f1cd8a3..e1cff62a45f 100644
--- a/test/jdk/com/sun/net/httpserver/ContextPathMatcherPathPrefixTest.java
+++ b/test/jdk/com/sun/net/httpserver/ContextPathMatcherPathPrefixTest.java
@@ -37,6 +37,7 @@ import static java.net.http.HttpClient.Builder.NO_PROXY;
 import org.junit.jupiter.api.AfterAll;
 
 import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertThrows;
 
 import org.junit.jupiter.api.Test;
 
@@ -72,7 +73,7 @@ import org.junit.jupiter.api.Test;
 
 public class ContextPathMatcherPathPrefixTest {
 
-    private static final HttpClient CLIENT =
+    protected static final HttpClient CLIENT =
             HttpClient.newBuilder().proxy(NO_PROXY).build();
 
     @AfterAll
@@ -80,6 +81,12 @@ public class ContextPathMatcherPathPrefixTest {
         CLIENT.shutdownNow();
     }
 
+    @Test
+    void testContextPathOfEmptyString() {
+        var iae = assertThrows(IllegalArgumentException.class, () -> new Infra(""));
+        assertEquals("Illegal value for path or protocol", iae.getMessage());
+    }
+
     @Test
     void testContextPathAtRoot() throws Exception {
         try (var infra = new Infra("/")) {
@@ -103,7 +110,7 @@ public class ContextPathMatcherPathPrefixTest {
         }
     }
 
-    public static final class Infra implements AutoCloseable {
+    protected static final class Infra implements AutoCloseable {
 
         private static final InetSocketAddress LO_SA_0 =
                 new InetSocketAddress(InetAddress.getLoopbackAddress(), 0);
@@ -114,14 +121,14 @@ public class ContextPathMatcherPathPrefixTest {
 
         private final String contextPath;
 
-        public Infra(String contextPath) throws IOException {
+        protected Infra(String contextPath) throws IOException {
             this.server = HttpServer.create(LO_SA_0, 10);
             server.createContext(contextPath, HANDLER);
             server.start();
             this.contextPath = contextPath;
         }
 
-        public void expect(int statusCode, String... requestPaths) throws Exception {
+        protected void expect(int statusCode, String... requestPaths) throws Exception {
             for (String requestPath : requestPaths) {
                 var requestURI = URI.create("http://%s:%s%s".formatted(
                         server.getAddress().getHostString(),
diff --git a/test/jdk/com/sun/net/httpserver/ContextPathMatcherStringPrefixTest.java b/test/jdk/com/sun/net/httpserver/ContextPathMatcherStringPrefixTest.java
index 685b8f02be0..3f3008a8531 100644
--- a/test/jdk/com/sun/net/httpserver/ContextPathMatcherStringPrefixTest.java
+++ b/test/jdk/com/sun/net/httpserver/ContextPathMatcherStringPrefixTest.java
@@ -21,13 +21,8 @@
  * questions.
  */
 
-import org.junit.jupiter.api.AfterAll;
 import org.junit.jupiter.api.Test;
 
-import java.net.http.HttpClient;
-
-import static java.net.http.HttpClient.Builder.NO_PROXY;
-
 /*
  * @test
  * @bug 8272758
@@ -39,33 +34,28 @@ import static java.net.http.HttpClient.Builder.NO_PROXY;
  *      ${test.main.class}
  */
 
-class ContextPathMatcherStringPrefixTest {
-
-    private static final HttpClient CLIENT =
-            HttpClient.newBuilder().proxy(NO_PROXY).build();
-
-    @AfterAll
-    static void stopClient() {
-        CLIENT.shutdownNow();
-    }
+class ContextPathMatcherStringPrefixTest extends ContextPathMatcherPathPrefixTest {
 
     @Test
+    @Override
     void testContextPathAtRoot() throws Exception {
-        try (var infra = new ContextPathMatcherPathPrefixTest.Infra("/")) {
+        try (var infra = new Infra("/")) {
             infra.expect(200, "/foo", "/foo/", "/foo/bar", "/foobar");
         }
     }
 
     @Test
+    @Override
     void testContextPathAtSubDir() throws Exception {
-        try (var infra = new ContextPathMatcherPathPrefixTest.Infra("/foo")) {
+        try (var infra = new Infra("/foo")) {
             infra.expect(200, "/foo", "/foo/", "/foo/bar", "/foobar");
         }
     }
 
     @Test
+    @Override
     void testContextPathAtSubDirWithTrailingSlash() throws Exception {
-        try (var infra = new ContextPathMatcherPathPrefixTest.Infra("/foo/")) {
+        try (var infra = new Infra("/foo/")) {
             infra.expect(200, "/foo/", "/foo/bar");
             infra.expect(404, "/foo", "/foobar");
         }