diff --git a/.github/workflows/build_executable.yml b/.github/workflows/build_executable.yml
index dc1d34fe..94f285ce 100644
--- a/.github/workflows/build_executable.yml
+++ b/.github/workflows/build_executable.yml
@@ -58,12 +58,6 @@ jobs:
           LATEST_TAG=$(git describe --tags `git rev-list --tags --max-count=1`)
           git checkout $LATEST_TAG
           echo "LATEST_TAG=$LATEST_TAG" >> $GITHUB_ENV
-
-      - name: Upgrade OpenSSL on macOS Builder
-        if: runner.os == 'macOS'
-        run: |
-          brew update
-          brew upgrade openssl@3
           
       - name: Set up Python 3.13
         id: setup-python
diff --git a/pyinstaller.spec b/pyinstaller.spec
index d93766a8..e5be2bc2 100644
--- a/pyinstaller.spec
+++ b/pyinstaller.spec
@@ -2,6 +2,10 @@
 # Run `poetry run pyinstaller pyinstaller.spec` to generate the binary.
 # Set the env var `CYCODE_ONEDIR_MODE` to generate a single directory instead of a single file.
 
+import os
+import platform
+import subprocess
+
 _INIT_FILE_PATH = os.path.join('cycode', '__init__.py')
 _CODESIGN_IDENTITY = os.environ.get('APPLE_CERT_NAME')
 _ONEDIR_MODE = os.environ.get('CYCODE_ONEDIR_MODE') is not None
@@ -43,6 +47,24 @@ a = Analysis(
     hiddenimports=_hiddenimports,
 )
 
+if platform.system() == 'Darwin':
+    # cryptography ships no macOS x86_64 wheel since 46.0.4, so on Intel it is built from source and
+    # dynamically links Homebrew's OpenSSL 3 (it needs symbols like `SSL_get0_group_name`, added in
+    # OpenSSL 3.2). PyInstaller also collects the older OpenSSL 3.0.x that ships with the
+    # setup-python toolcache Python; both land at the same destination name and the toolcache copy
+    # wins the dedup, which breaks `import cryptography` at runtime. Drop every collected
+    # libssl/libcrypto and inject Homebrew's, which satisfies both consumers.
+    try:
+        openssl_lib = os.path.join(
+            subprocess.check_output(['brew', '--prefix', 'openssl@3'], text=True).strip(), 'lib'
+        )
+        a.binaries = [b for b in a.binaries if 'libssl' not in b[0] and 'libcrypto' not in b[0]]
+        for name in ('libssl.3.dylib', 'libcrypto.3.dylib'):
+            a.binaries.append((name, os.path.join(openssl_lib, name), 'BINARY'))
+        print(f'Replaced collected OpenSSL dylibs with Homebrew ones from {openssl_lib}')
+    except Exception as e:
+        print(f'Warning: Could not override OpenSSL binaries: {e}')
+
 exe_args = [PYZ(a.pure), a.scripts, a.binaries, a.datas]
 if _ONEDIR_MODE:
     exe_args = [PYZ(a.pure), a.scripts]