diff --git a/cpython-unix/build-cpython.sh b/cpython-unix/build-cpython.sh
index 7deb00830..e908c0f32 100755
--- a/cpython-unix/build-cpython.sh
+++ b/cpython-unix/build-cpython.sh
@@ -1063,6 +1063,20 @@ replace_in_all("-L%s/deps/lib" % tools_path, "")
 # See https://github.com/python/cpython/issues/145810#issuecomment-4068139183
 replace_in_all("-LModules/_hacl", "")
 
+# Strip toolchain bin directory prefix from sysconfig artifacts to avoid exposing
+# build-time paths. This primarily fixes AR (e.g., /tools/llvm/bin/llvm-ar -> llvm-ar),
+# which is not normalized by CPython, and also catches RANLIB and similar tools.
+# See https://github.com/astral-sh/python-build-standalone/issues/1073
+toolchain = os.environ["TOOLCHAIN"]
+toolchain_bin = os.path.normpath(os.path.join(tools_path, toolchain, "bin"))
+toolchain_bin_norm = toolchain_bin + "/"
+replace_in_all(toolchain_bin_norm, "")
+
+# Also catch resolved symlinks (e.g., macOS /var vs /private/var).
+toolchain_bin_real = os.path.realpath(toolchain_bin) + "/"
+if toolchain_bin_real != toolchain_bin_norm:
+    replace_in_all(toolchain_bin_real, "")
+
 EOF
 
 ${BUILD_PYTHON} "${ROOT}/hack_sysconfig.py" "${ROOT}/out/python"
diff --git a/test_ar_normalization.py b/test_ar_normalization.py
new file mode 100644
index 000000000..e64883f2d
--- /dev/null
+++ b/test_ar_normalization.py
@@ -0,0 +1,58 @@
+#!/usr/bin/env python3
+"""Test that AR normalization works correctly."""
+import os
+
+def test_ar_normalization():
+    """Simulate the string replacement to verify it works."""
+    # Simulated sysconfig data
+    test_cases = [
+        # (input, expected_output, description)
+        ("AR = /tools/llvm/bin/llvm-ar", "AR = llvm-ar", "Basic AR case"),
+        ("RANLIB = /tools/llvm/bin/llvm-ranlib", "RANLIB = llvm-ranlib", "RANLIB case"),
+        ("CC = /tools/llvm/bin/clang -pthread", "CC = clang -pthread", "CC with flags"),
+        ("CXX = /tools/llvm/bin/clang++ -pthread", "CXX = clang++ -pthread", "CXX with flags"),
+        # Edge cases
+        ("PATH=/tools/llvm/bin:/usr/bin", "PATH=/tools/llvm/bin:/usr/bin", "PATH unchanged (no trailing /)"),
+        ("Some random text", "Some random text", "No match - unchanged"),
+        # Path normalization: our search pattern is normalized, so double-slash
+        # in sysconfig data won't match (but that's OK - sysconfig should be normalized)
+        ("AR = /tools//llvm/bin/llvm-ar", "AR = /tools//llvm/bin/llvm-ar", "Double slash in data won't match (expected)"),
+        # Empty value after replacement (edge case)
+        ("AR = /tools/llvm/bin/", "AR = ", "Trailing slash creates empty value (acceptable)"),
+    ]
+
+    tools_path = "/tools"
+    toolchain = "llvm"
+
+    # Use os.path.normpath to handle edge cases like double slashes
+    toolchain_bin = os.path.normpath(os.path.join(tools_path, toolchain, "bin"))
+    search = toolchain_bin + "/"
+    replace = ""
+
+    print(f"Testing replacement: '{search}' -> '{replace}'")
+    print("-" * 60)
+
+    all_passed = True
+    for input_str, expected, description in test_cases:
+        output = input_str.replace(search, replace)
+        passed = output == expected
+        status = "✓" if passed else "✗"
+
+        print(f"{status} {description}")
+        if not passed:
+            print(f"  Input:    {input_str}")
+            print(f"  Expected: {expected}")
+            print(f"  Got:      {output}")
+            all_passed = False
+
+    print("-" * 60)
+    if all_passed:
+        print("All tests passed!")
+        return 0
+    else:
+        print("Some tests failed!")
+        return 1
+
+if __name__ == "__main__":
+    import sys
+    sys.exit(test_ar_normalization())