diff --git a/src/jdk.zipfs/share/classes/jdk/nio/zipfs/ZipFileSystem.java b/src/jdk.zipfs/share/classes/jdk/nio/zipfs/ZipFileSystem.java
index 7b478151c43e8..cecb8b86a2dc8 100644
--- a/src/jdk.zipfs/share/classes/jdk/nio/zipfs/ZipFileSystem.java
+++ b/src/jdk.zipfs/share/classes/jdk/nio/zipfs/ZipFileSystem.java
@@ -646,6 +646,8 @@ void setPermissions(byte[] path, Set<PosixFilePermission> perms) throws IOExcept
             }
             if (perms == null) {
                 e.posixPerms = -1;
+            } else if (e.posixPerms == -1) {
+                e.posixPerms = ZipUtils.permsToFlags(perms);
             } else {
                 e.posixPerms = ZipUtils.permsToFlags(perms) |
                         (e.posixPerms & 0xFE00); // Preserve unrelated bits
diff --git a/test/jdk/jdk/nio/zipfs/TestPosix.java b/test/jdk/jdk/nio/zipfs/TestPosix.java
index 1fa3bdf2d7b26..179c6a55cfbf1 100644
--- a/test/jdk/jdk/nio/zipfs/TestPosix.java
+++ b/test/jdk/jdk/nio/zipfs/TestPosix.java
@@ -61,7 +61,7 @@
 
 /**
  * @test
- * @bug 8213031 8273935
+ * @bug 8213031 8273935 8324635
  * @summary Test POSIX ZIP file operations.
  * @modules jdk.zipfs
  *          jdk.jartool
@@ -719,7 +719,7 @@ public void testJarFile() throws IOException {
     }
 
     /**
-     * Verify that calling Files.setPosixPermissions with the current
+     * Verify that calling Files.setPosixFilePermissions with the current
      * permission set does not change the 'external file attributes' field.
      *
      * @throws IOException if an unexpected IOException occurs
@@ -733,6 +733,53 @@ public void setPermissionsShouldPreserveRemainingBits() throws IOException {
         });
     }
 
+    /**
+     * Verify that calling Files.setPosixFilePermissions on an MS-DOS entry
+     * results in only the expected permission bits being set
+     *
+     * @throws IOException if an unexpected IOException occurs
+     */
+    @Test
+    public void setPermissionsShouldConvertToUnix() throws IOException {
+        // The default environment creates MS-DOS entries, with zero 'external file attributes'
+        createEmptyZipFile(ZIP_FILE, ENV_DEFAULT);
+        try (FileSystem fs = FileSystems.newFileSystem(ZIP_FILE, ENV_DEFAULT)) {
+            Path path = fs.getPath("hello.txt");
+            Files.createFile(path);
+        }
+        // The CEN header is now as follows:
+        //
+        //   004A CENTRAL HEADER #1     02014B50
+        //   004E Created Zip Spec      14 '2.0'
+        //   004F Created OS            00 'MS-DOS'
+        //   0050 Extract Zip Spec      14 '2.0'
+        //   0051 Extract OS            00 'MS-DOS'
+        //   [...]
+        //   0070 Ext File Attributes   00000000
+
+        // Sanity check that all 'external file attributes' bits are all zero
+        verifyExternalFileAttribute(Files.readAllBytes(ZIP_FILE), "0");
+
+        // Convert to a UNIX entry by calling Files.setPosixFilePermissions
+        try (FileSystem fs = FileSystems.newFileSystem(ZIP_FILE, ENV_POSIX)) {
+            Path path = fs.getPath("hello.txt");
+            Files.setPosixFilePermissions(path, EnumSet.of(OWNER_READ));
+        }
+
+        // The CEN header should now be as follows:
+        //
+        // 004A CENTRAL HEADER #1     02014B50
+        // 004E Created Zip Spec      14 '2.0'
+        // 004F Created OS            03 'Unix'
+        // 0050 Extract Zip Spec      14 '2.0'
+        // 0051 Extract OS            00 'MS-DOS'
+        // [...]
+        // 0070 Ext File Attributes   01000000
+
+        // The first of the nine trailing permission bits should be set
+        verifyExternalFileAttribute(Files.readAllBytes(ZIP_FILE), "100000000");
+    }
+
     /**
      * Verify that a non-POSIX operation such as Files.setLastModifiedTime
      * does not change the 'external file attributes' field.