diff --git a/CHANGELOG.md b/CHANGELOG.md
index fa9a825..be088a8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,13 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## [0.10.2] - 2026-01-07
+
+### Bug Fixes
+
+- Fix SSL certificate verification for Nuitka binaries on macOS
+- Fix macOS stdlib download URL (use PyPy 3.8 v7.3.11)
+
 ## [0.10.1] - 2026-01-07
 
 ### Enhancements
diff --git a/pyproject.toml b/pyproject.toml
index ba4de22..bb092d5 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -4,7 +4,7 @@ build-backend = "setuptools.build_meta"
 
 [project]
 name = "shannot"
-version = "0.10.1"
+version = "0.10.2"
 description = "Sandboxed system administration for LLM agents"
 readme = "README.md"
 license = {text = "Apache-2.0"}
diff --git a/shannot/config.py b/shannot/config.py
index b178680..86d7dfe 100644
--- a/shannot/config.py
+++ b/shannot/config.py
@@ -82,9 +82,9 @@ def _xdg_config_home() -> Path:
         "sha256": "a23d21ca0de0f613732af4b4abb0b0db1cc56134b5bf0e33614eca87ab8805af",
     },
     "darwin": {
-        "version": "7.3.17",  # PyPy 3.8
-        "url": "https://downloads.python.org/pypy/pypy3.8-v7.3.17-src.tar.bz2",
-        "sha256": "7491a669e3abc3420aca0cfb58cc69f8e0defda4469f503fd6cb415ec93d6b13",
+        "version": "7.3.11",  # PyPy 3.8
+        "url": "https://downloads.python.org/pypy/pypy3.8-v7.3.11-src.tar.bz2",
+        "sha256": "4d6769bfca73734e8666fd70503b7ceb06a6e259110e617331bb3899ca4e6058",
     },
 }
 
diff --git a/shannot/deploy.py b/shannot/deploy.py
index 54948eb..250fd38 100644
--- a/shannot/deploy.py
+++ b/shannot/deploy.py
@@ -20,6 +20,7 @@
     get_remote_deploy_dir,
     get_version,
 )
+from .runtime import get_ssl_context
 from .ssh import SSHConnection
 
 if TYPE_CHECKING:
@@ -77,7 +78,8 @@ def _download_file(url: str, dest: Path, desc: str = "Downloading") -> None:
 
     try:
         request = urllib.request.Request(url, headers={"User-Agent": "shannot/1.0"})
-        with urllib.request.urlopen(request) as response:
+        ssl_context = get_ssl_context()
+        with urllib.request.urlopen(request, context=ssl_context) as response:
             total_size = int(response.headers.get("Content-Length", 0))
             downloaded = 0
 
diff --git a/shannot/runtime.py b/shannot/runtime.py
index 1cd9da6..d123fc1 100644
--- a/shannot/runtime.py
+++ b/shannot/runtime.py
@@ -6,6 +6,7 @@
 import os
 import platform
 import shutil
+import ssl
 import sys
 import tarfile
 import tempfile
@@ -32,6 +33,36 @@ class SetupError(Exception):
     pass
 
 
+def get_ssl_context() -> ssl.SSLContext:
+    """Get SSL context that works on macOS with Nuitka binaries.
+
+    Nuitka-compiled binaries on macOS can't find system SSL certificates.
+    This function tries multiple certificate locations.
+    """
+    # Try default context first (works on most systems)
+    ctx = ssl.create_default_context()
+
+    # On macOS, try known certificate locations if default fails verification
+    if platform.system() == "Darwin":
+        # Common certificate locations on macOS
+        cert_paths = [
+            "/etc/ssl/cert.pem",  # Homebrew OpenSSL
+            "/opt/homebrew/etc/openssl@3/cert.pem",  # Homebrew ARM64
+            "/usr/local/etc/openssl@3/cert.pem",  # Homebrew x86_64
+            "/opt/homebrew/etc/openssl/cert.pem",
+            "/usr/local/etc/openssl/cert.pem",
+        ]
+        for cert_path in cert_paths:
+            if os.path.exists(cert_path):
+                try:
+                    ctx = ssl.create_default_context(cafile=cert_path)
+                    break
+                except ssl.SSLError:
+                    continue
+
+    return ctx
+
+
 def is_runtime_installed() -> bool:
     """Check if runtime is installed and valid."""
     return RUNTIME_LIB_PYTHON.is_dir() and RUNTIME_LIB_PYPY.is_dir()
@@ -114,8 +145,9 @@ def download_with_progress(
 ) -> None:
     """Download URL to dest with optional progress reporting."""
     request = urllib.request.Request(url, headers={"User-Agent": "shannot/1.0"})
+    ssl_context = get_ssl_context()
 
-    with urllib.request.urlopen(request) as response:
+    with urllib.request.urlopen(request, context=ssl_context) as response:
         total_size = int(response.headers.get("Content-Length", 0))
         downloaded = 0
 
diff --git a/uv.lock b/uv.lock
index 47eba34..15c2168 100644
--- a/uv.lock
+++ b/uv.lock
@@ -793,7 +793,7 @@ wheels = [
 
 [[package]]
 name = "shannot"
-version = "0.10.0"
+version = "0.10.2"
 source = { editable = "." }
 
 [package.optional-dependencies]