diff --git a/src/main/automations/hermes-cron-output.test.ts b/src/main/automations/hermes-cron-output.test.ts
index d47984e80ab..5acbcd8c22d 100644
--- a/src/main/automations/hermes-cron-output.test.ts
+++ b/src/main/automations/hermes-cron-output.test.ts
@@ -174,6 +174,36 @@ Run summary: monitor automation completed successfully.
     )
   })
 
+  it('hydrates referenced logs in valid dot-dot-prefixed Hermes subdirectories', async () => {
+    const home = await createHermesHome()
+    const outputDir = join(home, 'cron', 'output', 'job-1')
+    const scriptLogPath = join(home, '..logs', 'x-monitor.log')
+    await mkdir(outputDir, { recursive: true })
+    await mkdir(dirname(scriptLogPath), { recursive: true })
+    await writeFile(scriptLogPath, 'dot-dot-prefixed log line\n', 'utf-8')
+    await writeFile(
+      join(outputDir, '2026-05-15_09-02-00.md'),
+      `# Cron Job: Monitor automation
+
+## Response
+
+Latest log path: ${scriptLogPath}
+Run summary: monitor automation completed successfully.
+`,
+      'utf-8'
+    )
+
+    const { readHermesCronOutputRunsPage } = await loadReader()
+    const page = await readHermesCronOutputRunsPage('job-1', { page: 1, pageSize: 25 })
+
+    expect((page.runs[0] as { output_content?: string }).output_content).toContain(
+      '## Latest log file'
+    )
+    expect((page.runs[0] as { output_content?: string }).output_content).toContain(
+      'dot-dot-prefixed log line'
+    )
+  })
+
   it('uses a count-only path when page size is zero', async () => {
     const home = await createHermesHome()
     const outputDir = join(home, 'cron', 'output', 'job-1')
diff --git a/src/main/automations/hermes-cron-output.ts b/src/main/automations/hermes-cron-output.ts
index c0c68d9a205..5f220468213 100644
--- a/src/main/automations/hermes-cron-output.ts
+++ b/src/main/automations/hermes-cron-output.ts
@@ -3,7 +3,7 @@
 import { existsSync } from 'fs'
 import { open, readdir, readFile, realpath, stat } from 'fs/promises'
 import { homedir } from 'os'
-import { isAbsolute, join, relative, resolve } from 'path'
+import { isAbsolute, join, relative, resolve, sep } from 'path'
 import Database from '../sqlite/sync-database'
 
 const HERMES_HOME = process.env.HERMES_HOME?.trim() || join(homedir(), '.hermes')
@@ -162,7 +162,11 @@ async function readReferencedLogFile(content: string): Promise<{
     const relativeToHermesHome = relative(resolve(homeRealPath), resolve(logRealPath))
     // Why: the output body can contain agent-authored text, so only hydrate
     // referenced files that resolve inside Hermes' own data directory.
-    if (relativeToHermesHome.startsWith('..') || isAbsolute(relativeToHermesHome)) {
+    if (
+      relativeToHermesHome === '..' ||
+      relativeToHermesHome.startsWith(`..${sep}`) ||
+      isAbsolute(relativeToHermesHome)
+    ) {
       return null
     }
     const logStat = await stat(logPath)
diff --git a/src/relay/external-automations-handler-log-path.test.ts b/src/relay/external-automations-handler-log-path.test.ts
new file mode 100644
index 00000000000..936cf4cff8a
--- /dev/null
+++ b/src/relay/external-automations-handler-log-path.test.ts
@@ -0,0 +1,47 @@
+import { mkdtemp, mkdir, rm, writeFile } from 'fs/promises'
+import { tmpdir } from 'os'
+import { dirname, join } from 'path'
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
+import type { RelayDispatcher } from './dispatcher'
+
+type ReferencedLogReader = {
+  readReferencedLogFile(content: string): Promise<{ content: string } | null>
+}
+
+describe('ExternalAutomationsHandler referenced log paths', () => {
+  let hermesHome: string
+  let previousHermesHome: string | undefined
+
+  beforeEach(async () => {
+    previousHermesHome = process.env.HERMES_HOME
+    hermesHome = await mkdtemp(join(tmpdir(), 'relay-hermes-output-'))
+    process.env.HERMES_HOME = hermesHome
+    vi.resetModules()
+  })
+
+  afterEach(async () => {
+    if (previousHermesHome === undefined) {
+      delete process.env.HERMES_HOME
+    } else {
+      process.env.HERMES_HOME = previousHermesHome
+    }
+    await rm(hermesHome, { recursive: true, force: true })
+    vi.resetModules()
+  })
+
+  it('hydrates referenced logs in valid dot-dot-prefixed Hermes subdirectories', async () => {
+    const logPath = join(hermesHome, '..logs', 'x-monitor.log')
+    await mkdir(dirname(logPath), { recursive: true })
+    await writeFile(logPath, 'remote dot-dot-prefixed log line\n', 'utf-8')
+
+    const { ExternalAutomationsHandler } = await import('./external-automations-handler')
+    const handler = new ExternalAutomationsHandler({
+      onRequest: () => {}
+    } as unknown as RelayDispatcher) as unknown as ReferencedLogReader
+
+    const result = await handler.readReferencedLogFile(`Latest log path: ${logPath}
+Run summary: monitor automation completed successfully.`)
+
+    expect(result?.content).toBe('remote dot-dot-prefixed log line\n')
+  })
+})
diff --git a/src/relay/external-automations-handler.ts b/src/relay/external-automations-handler.ts
index 0062a5b0eb0..ff82d268b3a 100644
--- a/src/relay/external-automations-handler.ts
+++ b/src/relay/external-automations-handler.ts
@@ -5,7 +5,7 @@ import { existsSync } from 'fs'
 import { open, readdir, readFile, realpath, stat } from 'fs/promises'
 import { createRequire } from 'module'
 import { homedir } from 'os'
-import { isAbsolute, join, relative, resolve } from 'path'
+import { isAbsolute, join, relative, resolve, sep } from 'path'
 import { promisify } from 'util'
 import type { RelayDispatcher } from './dispatcher'
 
@@ -246,7 +246,11 @@ export class ExternalAutomationsHandler {
       const relativeToHermesHome = relative(resolve(homeRealPath), resolve(logRealPath))
       // Why: the output body can contain agent-authored text, so only hydrate
       // referenced files that resolve inside Hermes' own data directory.
-      if (relativeToHermesHome.startsWith('..') || isAbsolute(relativeToHermesHome)) {
+      if (
+        relativeToHermesHome === '..' ||
+        relativeToHermesHome.startsWith(`..${sep}`) ||
+        isAbsolute(relativeToHermesHome)
+      ) {
         return null
       }
       const logStat = await stat(logPath)