diff --git a/cmake/targets/BuildBun.cmake b/cmake/targets/BuildBun.cmake
index 664ed8e1dc..f3f74f9fc4 100644
--- a/cmake/targets/BuildBun.cmake
+++ b/cmake/targets/BuildBun.cmake
@@ -685,7 +685,7 @@ if(WIN32)
     ${CODEGEN_PATH}/windows-app-info.rc
     @ONLY
   )
-  set(WINDOWS_RESOURCES ${CODEGEN_PATH}/windows-app-info.rc)
+  set(WINDOWS_RESOURCES ${CODEGEN_PATH}/windows-app-info.rc ${CWD}/src/bun.exe.manifest)
 endif()
 
 # --- Executable ---
diff --git a/src/bun.exe.manifest b/src/bun.exe.manifest
new file mode 100644
index 0000000000..14791b7661
--- /dev/null
+++ b/src/bun.exe.manifest
@@ -0,0 +1,10 @@
+<?xml version="1.0" encoding="UTF-8" standalone="yes"?>
+<assembly xmlns="urn:schemas-microsoft-com:asm.v1" manifestVersion="1.0"
+          xmlns:asmv3="urn:schemas-microsoft-com:asm.v3">
+  <asmv3:application>
+    <asmv3:windowsSettings>
+      <longPathAware xmlns="http://schemas.microsoft.com/SMI/2016/WindowsSettings">true</longPathAware>
+      <heapType xmlns="http://schemas.microsoft.com/SMI/2020/WindowsSettings">SegmentHeap</heapType>
+    </asmv3:windowsSettings>
+  </asmv3:application>
+</assembly>
\ No newline at end of file
diff --git a/src/windows-app-info.rc b/src/windows-app-info.rc
index e060d39d81..7537bf1db6 100644
--- a/src/windows-app-info.rc
+++ b/src/windows-app-info.rc
@@ -5,6 +5,12 @@ IDI_MYICON ICON "@BUN_ICO_PATH@"
 VS_VERSION_INFO VERSIONINFO
 FILEVERSION @Bun_VERSION_MAJOR@,@Bun_VERSION_MINOR@,@Bun_VERSION_PATCH@,0
 PRODUCTVERSION @Bun_VERSION_MAJOR@,@Bun_VERSION_MINOR@,@Bun_VERSION_PATCH@,0
+FILEFLAGSMASK 0x3fL
+#ifdef _DEBUG
+FILEFLAGS 0x1L
+#else
+FILEFLAGS 0x0L
+#endif
 FILEOS 0x4L
 FILETYPE 0x1L
 FILESUBTYPE 0x0L