diff --git a/src/security.ts b/src/security.ts
index 12e0019e..65bcfad9 100644
--- a/src/security.ts
+++ b/src/security.ts
@@ -1,4 +1,4 @@
-import { readFileSync } from "node:fs";
+import { readFileSync, realpathSync } from "node:fs";
 import { resolve } from "node:path";
 import { homedir } from "node:os";
 
@@ -429,19 +429,54 @@ export function evaluateCommandDenyOnly(
  *
  * Normalizes backslashes to forward slashes before matching so that
  * Windows paths work with Unix-style glob patterns.
+ *
+ * When `projectRoot` is supplied, the path is also matched in its
+ * fully-resolved absolute form **and** — when the file exists — in
+ * its canonical form (`fs.realpathSync`). This prevents two classes
+ * of bypass:
+ *
+ *   1. `..` traversal: a relative path like `../../.ssh/id_rsa` no
+ *      longer evades absolute-path deny rules.
+ *   2. Symlink escape: a project-local path whose realpath points
+ *      outside the project (e.g. `safe.log -> ~/.ssh/id_rsa`) no
+ *      longer evades absolute-path deny rules.
+ *
+ * realpath is best-effort: if the file does not exist yet (ENOENT)
+ * or the syscall fails for any reason, the lexical resolved form is
+ * still checked. This keeps the function usable for paths that will
+ * be created during execution.
  */
 export function evaluateFilePath(
   filePath: string,
   denyGlobs: string[][],
   caseInsensitive: boolean = process.platform === "win32",
+  projectRoot?: string,
 ): { denied: boolean; matchedPattern?: string } {
-  // Normalize backslashes to forward slashes for cross-platform matching
-  const normalized = filePath.replace(/\\/g, "/");
+  const toForward = (path: string): string => path.replace(/\\/g, "/");
+
+  // Match against the raw input, the lexically-resolved absolute path,
+  // and the canonical (symlink-resolved) path when the file exists.
+  // Deduplicated so absolute inputs and paths that don't cross symlinks
+  // don't pay the matching cost multiple times.
+  const candidates = new Set<string>();
+  candidates.add(toForward(filePath));
+  if (projectRoot) {
+    const lexical = resolve(projectRoot, filePath);
+    candidates.add(toForward(lexical));
+    try {
+      candidates.add(toForward(realpathSync(lexical)));
+    } catch {
+      // File does not exist yet, or realpath failed — rely on lexical form.
+    }
+  }
 
   for (const globs of denyGlobs) {
     for (const glob of globs) {
-      if (fileGlobToRegex(glob, caseInsensitive).test(normalized)) {
-        return { denied: true, matchedPattern: glob };
+      const regex = fileGlobToRegex(glob, caseInsensitive);
+      for (const candidate of candidates) {
+        if (regex.test(candidate)) {
+          return { denied: true, matchedPattern: glob };
+        }
       }
     }
   }
diff --git a/src/server.ts b/src/server.ts
index 93249a91..8ddeb61f 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -371,8 +371,14 @@ function checkFilePathDenyPolicy(
   toolName: string,
 ): ToolResult | null {
   try {
-    const denyGlobs = readToolDenyPatterns("Read", process.env.CLAUDE_PROJECT_DIR);
-    const result = evaluateFilePath(filePath, denyGlobs);
+    const projectDir = process.env.CLAUDE_PROJECT_DIR ?? process.cwd();
+    const denyGlobs = readToolDenyPatterns("Read", projectDir);
+    const result = evaluateFilePath(
+      filePath,
+      denyGlobs,
+      process.platform === "win32",
+      projectDir,
+    );
     if (result.denied) {
       return trackResponse(toolName, {
         content: [{
diff --git a/tests/hooks/tool-naming.test.ts b/tests/hooks/tool-naming.test.ts
index 34afb550..0ce6bdcb 100644
--- a/tests/hooks/tool-naming.test.ts
+++ b/tests/hooks/tool-naming.test.ts
@@ -53,7 +53,7 @@ const mcpSentinel = resolve(tmpdir(), `context-mode-mcp-ready-${process.ppid}`);
 
 beforeEach(() => {
   if (typeof resetGuidanceThrottle === "function") resetGuidanceThrottle();
-  writeFileSync(mcpSentinel, String(process.pid));
+  writeFileSync(mcpSentinel, String(process.ppid));
 });
 
 afterEach(() => {
diff --git a/tests/security.test.ts b/tests/security.test.ts
index 9796c3a4..eeabc0e6 100644
--- a/tests/security.test.ts
+++ b/tests/security.test.ts
@@ -8,8 +8,8 @@
 import { describe, test, beforeAll, afterAll } from "vitest";
 import { strict as assert } from "node:assert";
 import { writeFileSync, mkdirSync, rmSync } from "node:fs";
-import { join } from "node:path";
-import { tmpdir } from "node:os";
+import { join, resolve } from "node:path";
+import { tmpdir, homedir } from "node:os";
 
 import {
   parseBashPattern,
@@ -474,6 +474,36 @@ describe("evaluateFilePath", () => {
     assert.equal(result.denied, true);
     assert.equal(result.matchedPattern, "**/.env");
   });
+
+  test("evaluateFilePath: traversal does not bypass absolute deny glob when projectRoot is supplied", () => {
+    // An absolute deny rule for ~/.ssh/** should still match when the caller
+    // passes a ../-traversal relative path that resolves into ~/.ssh.
+    const home = homedir();
+    const projectRoot = resolve(home, "some/project");
+    const denyGlob = resolve(home, ".ssh").replace(/\\/g, "/") + "/**";
+
+    const result = evaluateFilePath(
+      "../../.ssh/id_rsa",
+      [[denyGlob]],
+      process.platform === "win32",
+      projectRoot,
+    );
+    assert.equal(result.denied, true);
+    assert.equal(result.matchedPattern, denyGlob);
+  });
+
+  test("evaluateFilePath: without projectRoot, absolute deny glob is still bypassable (regression guard)", () => {
+    // Documents the pre-fix behavior: without projectRoot, `..` is not
+    // resolved, so the raw string doesn't match the absolute glob.
+    // This test exists so any change in behavior is intentional.
+    const absoluteSshGlob = resolve(homedir(), ".ssh").replace(/\\/g, "/") + "/**";
+    const result = evaluateFilePath(
+      "../../.ssh/id_rsa",
+      [[absoluteSshGlob]],
+      process.platform === "win32",
+    );
+    assert.equal(result.denied, false);
+  });
 });
 
 describe("Shell-Escape Scanner", () => {