Audit Xcode Security Settings

Audit Xcode Security Settings

Assess an Xcode project's security posture and progressively enable security build settings and entitlements — from broadly applicable warnings through Enhanced Security hardening.

Tool Preferences

When GetTargetBuildSettings writes its output to a saved file due to a token limit, see references/reading-build-settings.md for the schema and the filter script (scripts/filter_build_settings.py). Do not read the saved file linearly.

When XcodeGlob, XcodeGrep, XcodeRead, and XcodeLS tools are available, ALWAYS use them. Do not fall back to Bash filesystem tools (ls, find, cat, grep) to learn about the project. They trigger extra permission prompts and bypass project scoping.

• XcodeGlob for file discovery — find is forbidden for files inside the project.
• XcodeGrep for content search — grep/rg is forbidden for files inside the project.
• XcodeRead for file contents — cat/Read is forbidden for files registered in the project.
• XcodeLS for directory listing — ls is forbidden for any path inside the project.

Project root and name are already in the system prompt context. Do NOT run ls to "verify" the project layout before starting. The system prompt already tells you the working directory and the project structure.

Empty XcodeGlob results are not a failure. The .xcodeproj and .xcworkspace are not indexed as files inside the Xcode project organization — XcodeGlob "**/*.xcodeproj" correctly returns 0 matches. Use the project name from system-prompt context instead. Do not fall back to filesystem ls/find.

Path translation between project-org and filesystem. XcodeGlob returns project-org-relative paths. To read or edit a file:

• Prefer XcodeRead / XcodeUpdate with the project-org path.
• If that path is rejected (some on-disk files like .entitlements plists may not be navigable through XcodeRead), translate to a filesystem absolute path by prepending the project root from system context. Do NOT use find to discover the on-disk path.

Fall back to Bash only for operations the Xcode tools cannot do (e.g., plutil for plist editing, git operations).

Common Failure Modes

Workflow

Phase 0: Discovery

Read the system prompt context. It contains:

• The project root (working directory).
• The project name and structure (top-level files, packages).
• The active scheme.

Do not call ls, find, or any filesystem tool to re-discover this information.

Track Progress

Before starting Phase 1:

1. Print the workflow plan to the user as a visible bullet list (so non-verbose users can see what's coming):

   Workflow:

   • Phase 1: Analyze project and existing settings
   • Phase 2: Apply settings
     • Step 1: Enhanced Security
     • Step 2: Basic Clang safety warnings
   • Phase 3: Inquire about disabled settings
   • Phase 4: Validate applied settings
   • Phase 5: Report and update decision document
   • Phase 6: Optional follow-ups

2. Call TaskCreate with the same items so verbose users get a tracker.

When entering each phase or sub-step:

• Print one line: "▶ Phase N: …" (or "▶ Phase 2 / Step 1: …" for sub-steps).
• Update the task to in_progress.

When finishing each phase or sub-step:

• Print one line: "✓ Phase N: …" (with a brief outcome if applicable, e.g., "✓ Phase 3: No disabled settings found.").
• Update the task to completed.

Phase 6 starts as a single task and a single line. When the user opts into a specific follow-up, print "▶ Phase 6 / " at start and "✓ Phase 6 / " at end, and create/update the corresponding sub-task.

Phase 1: Analyze Project and Settings

No user interaction. Gather facts silently. Prefer XcodeGlob, XcodeGrep, and XcodeRead over Bash equivalents when available (see Tool Preferences).

1. Find .xcodeproj or .xcworkspace via XcodeGlob (**/*.xcodeproj) or Glob.
2. Search for an existing decision document (**/xcode-security-settings.md) via XcodeGlob or Glob. If found, read it and extract: languages and all prior setting decisions with their statuses and rationale. This informs subsequent phases.
3. Detect languages present via XcodeGlob or Glob:
   • **/*.c → C
   • **/*.cpp, **/*.cxx, **/*.cc → C++
   • **/*.m → Objective-C
   • **/*.mm → Objective-C++
   • **/*.swift → Swift
4. Enumerate targets and their entitlements files — for each target, record its product type, platform (via SDKROOT / SUPPORTED_PLATFORMS), and resolve CODE_SIGN_ENTITLEMENTS to the on-disk .entitlements path (per configuration if it varies). Phase 2 Step 1 needs this map. When using GetTargetBuildSettings, see references/reading-build-settings.md for the output schema and the recipe for handling large results.

Phase 2: Apply Settings

Apply settings progressively, from most applicable to least.

Check existing security settings. Grep pbxproj and xcconfig files for settings from the catalog (see references/settings-and-entitlements-catalog.md). Only apply settings that aren't already set. If everything is already enabled, tell the user and stop.

How to apply build settings:

• Project uses .xcconfig files — edit the xcconfig directly. Supports both project-level and target-level settings.
• Project uses .pbxproj only — use UpdateTargetBuildSetting for target-level settings and UpdateProjectBuildSetting for project-level settings.
• Mixed — if a target has an .xcconfig file, edit the xcconfig. Otherwise, use the Xcode build setting tools. Never introduce a new configuration method.

Prefer project-level when possible (less duplication). Fall back to target-level via UpdateTargetBuildSetting when the project doesn't use xcconfig.

Exception — ENABLE_ENHANCED_SECURITY: Must be set at project level. If the project uses xcconfig, set it there. Otherwise, use UpdateProjectBuildSetting.

Step 1: Enhanced Security — Audit entitlements + build settings, then propose per-target diffs

Read references/enhanced-security.md for the full key list, defaults, deprecated keys, version migration, and the supported product-type list. For details on individual sub-options, see:

• references/pointer-authentication.md — arm64e pointer signing
• references/typed-allocators.md — type-aware memory allocation
• references/stack-zero-init.md — automatic stack variable zeroing
• references/readonly-platform-memory.md — dyld state protection
• references/runtime-restrictions.md — dylib and Mach message restrictions
• references/security-compiler-warnings.md — security-focused compiler warnings
• references/cpp-hardening.md — C++ stdlib hardening and bounds checking
• references/hardware-memory-tagging.md — ARM MTE

1. Identify suported targets. From the target map gathered in Phase 1 step 4, skip any target whose product type isn't in the "Supported Product Types" list in references/enhanced-security.md. Remaining targets are "supported targets." Note: DriverKit targets are supported for build settings only — skip entitlement changes for them.

2. Audit each supported target. Gather build-setting values of ENABLE_ENHANCED_SECURITY and ENABLE_POINTER_AUTHENTICATION (check target-level, then project-level inherited). For non-DriverKit targets, also read the entitlements file and collect every key under com.apple.security.hardened-process*, including the deprecated keys. Compare against the required + default-ON keys in references/enhanced-security.md Part B and bucket each target:

   • Up-to-date — nothing to do.
   • Partial — ENABLE_ENHANCED_SECURITY is YES, but missing default-ON sub-options, or has deprecated keys, or version "1" / deprecated version key present.
   • Off — ENABLE_ENHANCED_SECURITY is absent.
   • No entitlements file — target is supported but has no .entitlements file yet. If the user confirms applying, one will be created (see Step 5).

IMPORTANT Do not enable pointer authentication if the project has any binary dependencies (such as frameworks, xcframeworks, Swift Packages) that are not in this project from source. If the project does have such dependencies, list them and recommend that the user reach out to the vendor of the dependencies for a Universal binary that includes both arm64 and arm64e.

3. Build the change set. For each Partial or Off supported target, compose entitlement changes in this order (omit empty sections):

   • Add entitlements: missing required keys (com.apple.security.hardened-process, ...enhanced-security-version-string = "2") and missing default-ON sub-options (hardened-heap, dyld-ro, platform-restrictions-string = "2").
   • Remove entitlements: deprecated keys (...platform-restrictions, ...enhanced-security-version).
   • Update entitlements: version string "1" → "2" if present.

   If a supported target has no .entitlements file, include creating one and wiring CODE_SIGN_ENTITLEMENTS in the change set.

   Build settings: Follow "How to apply build settings" above. If the project uses xcconfig, set ENABLE_ENHANCED_SECURITY = YES at project level there. Otherwise, use UpdateProjectBuildSetting.

   Because a project-level ENABLE_ENHANCED_SECURITY = YES cascades ENABLE_POINTER_AUTHENTICATION = YES to every target, pre-write a target-level ENABLE_POINTER_AUTHENTICATION = NO override on each target whose platform doesn't support arm64e (detect via SDKROOT / SUPPORTED_PLATFORMS). Skip if the target already has an explicit target-level value.

   Do not auto-enable default-OFF sub-options (MTE family); report state and offer enablement in step 6 below.

4. Present and confirm. If every supported target is up-to-date, report that fact in one line and proceed to Step 2 (Basic Clang Safety Warnings) — do not ask an apply-confirmation when there is nothing to apply. Otherwise print the proposed list of targets to enable Enhanced Security on.

Then print a short summary of the benefits of enabling Enhanced Security in terms of the security protections it provides and code changes it may require.

Then ask once via AskUserQuestion: "Apply the Enhanced Security changes above?" Offer "Apply all", "Apply to a subset (choose targets)", "Skip Enhanced Security".

5. Apply.

   • Target-level ENABLE_POINTER_AUTHENTICATION = NO overrides on non-arm64e-platform targets via UpdateTargetBuildSetting. Skip targets where the user already has an explicit target-level value.
   • Edit existing per-target .entitlements plists directly — add required + default-ON keys, remove deprecated keys, migrate version-string "1" → "2" atomically.
   • For targets with no .entitlements file, create one and wire CODE_SIGN_ENTITLEMENTS to it.

   Report: "Enabled Enhanced Security on N target(s). Removed M deprecated entitlement(s). Upgraded version string to 2 on K target(s). Added arm64e override on T non-arm64e-platform target(s)."

6. Hardware memory tagging. Supported only for targets whose SUPPORTED_PLATFORMS (or SDKROOT) is macosx, iphoneos / iphonesimulator, or xros / xrsimulator. (Hardware backing is M5-class Apple silicon and later; tvOS, watchOS, and DriverKit targets are not supported.) Skip this step if Enhanced Security was not applied or if no modified target matches one of those platforms. Otherwise ask via AskUserQuestion: "Hardware memory tagging is available via com.apple.security.hardened-process.checked-allocations. Do you want to enable it?" If yes → read references/hardware-memory-tagging.md and apply it.

Step 2: Basic Clang Safety Warnings

For codebases with C, C++, Objective-C, and Objective-C++, apply without asking. For pure Swift codebases, skip this step. Skip settings already enabled. Unless annotated otherwise, all settings below apply to C/C++/ObjC/ObjC++.

• GCC_WARN_ABOUT_RETURN_TYPE = YES_ERROR
• GCC_WARN_UNINITIALIZED_AUTOS = YES_AGGRESSIVE
• CLANG_WARN_IMPLICIT_FALLTHROUGH = YES
• GCC_WARN_64_TO_32_BIT_CONVERSION = YES
• GCC_TREAT_IMPLICIT_FUNCTION_DECLARATIONS_AS_ERRORS = YES (C/ObjC/ObjC++ only)
• CLANG_ANALYZER_SECURITY_FLOATLOOPCOUNTER = YES
• CLANG_ANALYZER_SECURITY_INSECUREAPI_RAND = YES
• CLANG_ANALYZER_SECURITY_INSECUREAPI_STRCPY = YES

Report briefly: "Enabled additional compiler warnings."

Phase 3: Inquire about Disabled Settings

Grep pbxproj and xcconfig files for any build setting from references/settings-and-entitlements-catalog.md that is explicitly set to NO. Exclude ENABLE_POINTER_AUTHENTICATION = NO on targets whose platform doesn't support arm64e (the skill itself sets it there). Do flag ENABLE_POINTER_AUTHENTICATION = NO on arm64e-capable targets — that's a deliberate opt-out worth inquiring about. If no other disabled settings are found, skip this phase. Only consider settings relevant to the languages detected in Phase 1 — see the Scope column in the catalog.

For each disabled setting found, check whether it has an entry in the decision document with status Disabled and a rationale.

If there is a documented rationale in the decision document, note it in the report and move on. The rationale documents a prior decision that can be re-audited later.

If there is no entry in the decision document, ask the user:

"I found CLANG_ANALYZER_SECURITY_INSECUREAPI_RAND explicitly set to NO with no explanation. Is there a reason for this?"

If the user provides a reason, accept it and record the rationale in the decision document so future audits can re-evaluate it. If no reason, recommend re-enabling.

This also applies to any setting the skill would normally enable, such as ENABLE_ENHANCED_SECURITY. If any is already explicitly set to NO, follow the same decision-document-check-then-inquire flow.

Phase 4: Validate Settings

For each target modified in Phase 2, use GetTargetBuildSettings to verify that every build setting applied appears with the expected value. If a setting is missing or has an unexpected value, flag it in the report as potentially unsupported by the current Xcode version. See references/reading-build-settings.md for the output schema and the recipe for handling large results.

Phase 5: Report and Decision Document

Produce a lean summary:

1. Enabled: List project-wide settings that were enabled.
2. Enhanced Security per target: For each supported target, one line: target name, final status (up-to-date / applied / skipped-by-user), and a terse delta (entitlements added, deprecated keys removed, version bumps, whether an entitlements file was created). Roll up targets skipped because the product type isn't supported into a single line rather than one per target.
3. Already active: List settings that were already configured correctly.
4. Inquired: Settings that were found disabled and the outcome of the inquiry.

Decision document. Read references/decision-document.md and follow it to create or update the decision document.

Phase 6: Optional Follow-up Steps

Offer these one at a time, in order. Each is a separate yes/no question — do not combine them into a single multi-choice prompt. For recommended adoption order and a decision matrix based on language mix, see references/adoption-strategy.md.

1. Additional settings. Ask via AskUserQuestion: "There are additional diagnostic settings that could find more issues but may also produce false positives. Want to enable them?" If yes → read references/additional-settings.md and follow it.

2. Bounds safety programming models (only if C or C++ code present). For C projects, ask: "Want to look into adopting ENABLE_C_BOUNDS_SAFETY? It's an annotation-based programming model for C bounds safety — invoke Xcode's bounds-safety skill to get started." For C++ projects, ask: "Want to look into adopting ENABLE_CPLUSPLUS_BOUNDS_SAFE_BUFFERS? It enables C++ bounds-safe buffer patterns — invoke Xcode's bounds-safety skill to get started."

User-Facing Interaction Guidelines

• Keep replies lean. Short sentences.
• Keep user questions minimal. Two scheduled questions: the Enhanced Security apply-confirmation and the hardware memory tagging offer. Other questions are situational: inquiries about deliberately-disabled settings (only when an explicit = NO lacks a documented rationale) and the decision document location (first creation only).
• Report progress so the user can track: "Enabling...", "Evaluating...", "Keeping/Reverting..."
• Use AskUserQuestion for inquiring about disabled settings, for the Enhanced Security apply-confirmation (including offering "apply to a subset"), and for the decision document location (first creation only).
• When asking a question provide context the user needs to answer the question. For example, describe the benefit of the security protection before asking whether to enable it. Describe it in terms of the protection it provides, not how it is enabled.
• When emitting lists of Xcode build settings, use bullet lists Don't use comma-separated lists.