diff --git a/constraints/linux.txt b/constraints/linux.txt
index 67a531d..7c3c23c 100644
--- a/constraints/linux.txt
+++ b/constraints/linux.txt
@@ -106,7 +106,7 @@ pydantic-settings==2.14.1
     # via mcp
 pygments==2.20.0
     # via pytest
-pyinstaller==6.20.0
+pyinstaller==6.21.0
     # via plaud-tools (pyproject.toml)
 pyinstaller-hooks-contrib==2026.6
     # via pyinstaller
diff --git a/constraints/macos.txt b/constraints/macos.txt
index f284ac8..ad43aba 100644
--- a/constraints/macos.txt
+++ b/constraints/macos.txt
@@ -104,7 +104,7 @@ pydantic-settings==2.14.1
     # via mcp
 pygments==2.20.0
     # via pytest
-pyinstaller==6.20.0
+pyinstaller==6.21.0
     # via plaud-tools (pyproject.toml)
 pyinstaller-hooks-contrib==2026.6
     # via pyinstaller
diff --git a/constraints/windows.txt b/constraints/windows.txt
index 4c08d04..8f71cae 100644
--- a/constraints/windows.txt
+++ b/constraints/windows.txt
@@ -113,7 +113,7 @@ pydantic-settings==2.14.1
     # via mcp
 pygments==2.20.0
     # via pytest
-pyinstaller==6.20.0
+pyinstaller==6.21.0
     # via plaud-tools (pyproject.toml)
 pyinstaller-hooks-contrib==2026.6
     # via pyinstaller