diff --git a/src/main/codex/codex-hook-trust-grant.test.ts b/src/main/codex/codex-hook-trust-grant.test.ts
index 5f184355b58..cebe6ad20b6 100644
--- a/src/main/codex/codex-hook-trust-grant.test.ts
+++ b/src/main/codex/codex-hook-trust-grant.test.ts
@@ -31,6 +31,10 @@ let previousUserDataPath: string | undefined
 beforeEach(() => {
   userDataDir = mkdtempSync(join(tmpdir(), 'orca-trust-grant-userdata-'))
   runtimeHomeDir = join(userDataDir, 'codex-runtime-home', 'home')
+  // Why: production writes hooks.json before granting trust; keeping that
+  // ordering prevents test-only canonical-path drift during ledger setup.
+  mkdirSync(runtimeHomeDir, { recursive: true })
+  writeFileSync(join(runtimeHomeDir, 'hooks.json'), '{"hooks":{}}\n', 'utf-8')
   previousUserDataPath = process.env.ORCA_USER_DATA_PATH
   process.env.ORCA_USER_DATA_PATH = userDataDir
   codexAppServerCapabilityCache.clear()
diff --git a/src/main/codex/config-toml-trust.test.ts b/src/main/codex/config-toml-trust.test.ts
index bc5f847b629..9e8ae78cdc0 100644
--- a/src/main/codex/config-toml-trust.test.ts
+++ b/src/main/codex/config-toml-trust.test.ts
@@ -311,6 +311,16 @@ describe('computeTrustKey', () => {
     ).toBe(`${join(realpathSync.native(dirname(hooksPath)), 'hooks.json')}:stop:0:0`)
   })
 
+  it.skipIf(process.platform === 'win32')(
+    'canonicalizes an existing POSIX path with two leading slashes',
+    () => {
+      const hooksPath = `/${join(tmpDir, 'hooks.json')}`
+      writeFileSync(hooksPath, '{"hooks":{}}\n', 'utf-8')
+
+      expect(getCodexCanonicalTrustPath(hooksPath)).toBe(realpathSync.native(hooksPath))
+    }
+  )
+
   it('uses native Windows backslashes in the trust key Codex looks up', () => {
     // Why: Codex 0.140 writes approved Windows hook trust keys as raw native
     // paths under [hooks.state].
diff --git a/src/main/codex/config-toml-trust.ts b/src/main/codex/config-toml-trust.ts
index 87396638300..2e40f49895d 100644
--- a/src/main/codex/config-toml-trust.ts
+++ b/src/main/codex/config-toml-trust.ts
@@ -169,7 +169,9 @@ export function computeTrustKey(entry: CodexTrustEntry): string {
 }
 
 export function getCodexCanonicalTrustPath(sourcePath: string): string {
-  if (process.platform !== 'win32' && usesWindowsPathSeparators(sourcePath)) {
+  if (process.platform !== 'win32' && isWindowsDriveOrBackslashUncPath(sourcePath)) {
+    // Why: an existing `//` path is valid on POSIX, so let realpath distinguish
+    // it from forward-slash UNC before falling back to Windows normalization.
     return normalizeWindowsPathForCodexLookup(sourcePath)
   }
   try {
@@ -206,11 +208,11 @@ function normalizeWindowsPathSeparators(sourcePath: string): string {
 }
 
 function usesWindowsPathSeparators(sourcePath: string): boolean {
-  return (
-    /^[A-Za-z]:[\\/]/.test(sourcePath) ||
-    sourcePath.startsWith('\\\\') ||
-    sourcePath.startsWith('//')
-  )
+  return isWindowsDriveOrBackslashUncPath(sourcePath) || sourcePath.startsWith('//')
+}
+
+function isWindowsDriveOrBackslashUncPath(sourcePath: string): boolean {
+  return /^[A-Za-z]:[\\/]/.test(sourcePath) || sourcePath.startsWith('\\\\')
 }
 
 // Why: Codex and Orca can disagree on quote style, separators, and casing for