diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index 26894a3684..9123cd54d3 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -42,11 +42,21 @@ jobs:
          path: ~/.m2/repository
          key: ${{ runner.os }}-m2-repository-${{ hashFiles('**/pom.xml') }}
          restore-keys: ${{ runner.os }}-m2-repository
+    - name: Build Windows native executables
+      if: runner.os == 'Windows'
+      shell: cmd
+      run: |
+        call "C:\Program Files\Microsoft Visual Studio\2022\Enterprise\VC\Auxiliary\Build\vcvarsall.bat" x86
+        cd opendj-server-legacy\src\build-tools\windows
+        nmake all
+        xcopy /Y *.exe ..\..\..\lib\
+        git status
     - name: Set Integration Test Environment
       id: failsafe
       if: runner.os != 'Windows'
       run:   |
         echo "MAVEN_PROFILE_FLAG=-P precommit" >> $GITHUB_OUTPUT
+
     - name: Build with Maven
       timeout-minutes: 180
       env:
@@ -234,6 +244,21 @@ jobs:
         opendj-server-legacy\target\package\opendj\bat\rebuild-index.bat --bindDN "cn=Directory Manager" --bindPassword password --baseDN "dc=example2,dc=com" --rebuildAll --trustAll
         opendj-server-legacy\target\package\opendj\bat\ldapsearch.bat --hostname localhost --port 1636 --bindDN "cn=Directory Manager" --bindPassword password --useSsl --trustAll --baseDN "dc=example2,dc=com" --searchScope sub "(uid=user.*)" dn | find /c '"dn:"' | findstr "10000"
         opendj-server-legacy\target\package\opendj\bat\stop-ds.bat
+        opendj-server-legacy\target\package\opendj\bat\windows-service.bat --enableService
+        net start "OpenDJ Server"
+        for ($i=0; $i -lt 12; $i++) { try { $c = New-Object System.Net.Sockets.TcpClient('localhost', 1636); $c.Close(); break } catch { Start-Sleep -Seconds 5 } }
+        opendj-server-legacy\target\package\opendj\bat\ldapsearch.bat --hostname localhost --port 1636 --bindDN "cn=Directory Manager" --bindPassword password --useSsl --trustAll --baseDN "dc=example2,dc=com" --searchScope sub "(uid=user.*)" dn | find /c '"dn:"' | findstr "10000"
+        net stop "OpenDJ Server"
+        opendj-server-legacy\target\package\opendj\bat\windows-service.bat --disableService
+
+    - name: Upload Windows exe artifacts
+      if: runner.os == 'Windows'
+      uses: actions/upload-artifact@v4
+      with:
+        name: windows-exe-${{ matrix.java }}
+        retention-days: 5
+        path: opendj-server-legacy/src/build-tools/windows/*.exe
+
     - name: Upload artifacts OpenDJ Server
       uses: actions/upload-artifact@v4
       with:
diff --git a/opendj-server-legacy/src/build-tools/windows/service.c b/opendj-server-legacy/src/build-tools/windows/service.c
index 0f9f6e0fc0..42082bc2e3 100644
--- a/opendj-server-legacy/src/build-tools/windows/service.c
+++ b/opendj-server-legacy/src/build-tools/windows/service.c
@@ -13,6 +13,7 @@
  *
  * Copyright 2008-2010 Sun Microsystems, Inc.
  * Portions Copyright 2011-2013 ForgeRock AS.
+ * Portions Copyright 2026 3A Systems, LLC.
  */
 
 #include "service.h"
@@ -563,12 +564,44 @@ ServiceReturnCode doStartApplication()
 
   if (createOk && waitOk)
     {
-    BOOL running;
-      // Just check once if the server is running or not: since the wait
-      // wait was successful, if the server is getting the lock, it already
-      // got it.
-    isServerRunning(&running, TRUE);
-    if (running)
+      // The batch file process completed successfully, but the Java server
+      // process may not have acquired the lock file yet (especially on
+      // Windows 11 where JVM startup can be slower). Retry with a loop
+      // similar to the else-if branch below.
+      // See: https://github.com/OpenIdentityPlatform/OpenDJ/issues/259
+      const DWORD DEFAULT_TRIES = 100;
+      int nTries = DEFAULT_TRIES;
+      char * nTriesEnv = getenv("OPENDJ_WINDOWS_SERVICE_START_NTRIES");
+      BOOL running = FALSE;
+      if (nTriesEnv != NULL)
+      {
+        debug("OPENDJ_WINDOWS_SERVICE_START_NTRIES env var set to %s", nTriesEnv);
+        nTries = (int)strtol(nTriesEnv, (char **)NULL, 10);
+        if (nTries <= 0)
+        {
+          nTries = DEFAULT_TRIES;
+        }
+      }
+      else
+      {
+        debug("OPENDJ_WINDOWS_SERVICE_START_NTRIES is not set.  Using default %d tries.", nTries);
+      }
+
+      while ((nTries > 0) && !running)
+      {
+        nTries--;
+        if (isServerRunning(&running, TRUE) != SERVICE_RETURN_OK)
+        {
+          break;
+        }
+        if (!running)
+        {
+          debug("Sleeping for 5 seconds to allow the process to get the lock.  %d tries remaining.",
+              nTries);
+          Sleep(5000);
+        }
+      }
+      if (running)
       {
         returnValue = SERVICE_RETURN_OK;
         debug("doStartApplication: server running.");