diff --git a/src/main/ssh/build-toolchain-diagnosis.ts b/src/main/ssh/build-toolchain-diagnosis.ts
index dcec7a51237..77d20ce475a 100644
--- a/src/main/ssh/build-toolchain-diagnosis.ts
+++ b/src/main/ssh/build-toolchain-diagnosis.ts
@@ -174,10 +174,13 @@ const NODE_HEADERS_TARBALL_RE = /node-v[0-9.]+-headers\.tar\.gz/i
  * depends on what the local-headers export found first, so the formatter takes that answer.
  */
 export function isNodeHeadersDownloadFailure(message: string): boolean {
+  // Why `configure error` is required: node-gyp's fetch client logs `attempt N failed with <code>`
+  // on retries it then recovers from, so a network token alone also matches a build that got its
+  // headers and died later for an unrelated reason. Only the configure step downloads headers.
   return (
-    message.toLowerCase().includes('gyp') &&
+    /gyp ERR! configure error/i.test(message) &&
     NODE_HEADERS_TARBALL_RE.test(message) &&
-    /\b(ECONNREFUSED|ENOTFOUND|ETIMEDOUT|ECONNRESET|EAI_AGAIN|EHOSTUNREACH|ENETUNREACH|fetch failed|FetchError)\b/i.test(
+    /\b(ECONNREFUSED|ENOTFOUND|ETIMEDOUT|EHOSTUNREACH|ENETUNREACH|EAI_AGAIN|ECONNRESET)\b/.test(
       message
     )
   )
@@ -213,11 +216,11 @@ export function formatNodeHeadersDownloadError(
       ]
     : [
         'The remote host could not download the Node.js headers needed to compile node-pty, and ' +
-          `its Node install does not ship them locally. ${NODE_HEADERS_CONTEXT}`,
+          `its Node install has no local headers matching its own version. ${NODE_HEADERS_CONTEXT}`,
         '',
         'Fix one of the following on the remote host, then reconnect:',
         '  - Install Node.js from an official build or a version manager (nvm, fnm, volta, n), ' +
-          'which include the headers; or',
+          'which ship headers for exactly the Node they run; or',
         '  - Allow outbound HTTPS to nodejs.org, or point npm at a mirror: ' +
           'npm config set disturl https://<mirror>/dist'
       ]
diff --git a/src/main/ssh/ssh-relay-build-toolchain.test.ts b/src/main/ssh/ssh-relay-build-toolchain.test.ts
index 6d491887c33..6fcc4f5321d 100644
--- a/src/main/ssh/ssh-relay-build-toolchain.test.ts
+++ b/src/main/ssh/ssh-relay-build-toolchain.test.ts
@@ -140,7 +140,7 @@ describe('isNodeHeadersDownloadFailure', () => {
     expect(isNodeHeadersDownloadFailure(HEADERS_REFUSED)).toBe(true)
     expect(
       isNodeHeadersDownloadFailure(
-        'gyp http fetch GET https://nodejs.org/download/release/v20.19.0/node-v20.19.0-headers.tar.gz attempt 1 failed with ENOTFOUND'
+        'gyp http fetch GET https://nodejs.org/download/release/v20.19.0/node-v20.19.0-headers.tar.gz attempt 1 failed with ENOTFOUND\ngyp ERR! configure error'
       )
     ).toBe(true)
   })
@@ -159,13 +159,27 @@ describe('isNodeHeadersDownloadFailure', () => {
         'gyp info using node-v24.12.0-headers.tar.gz\ngyp ERR! build error make failed with exit code: 2'
       )
     ).toBe(false)
+    // A retried attempt that recovered, then a compile failure: not a download failure.
+    expect(
+      isNodeHeadersDownloadFailure(
+        'gyp http fetch GET https://nodejs.org/download/release/v24.12.0/node-v24.12.0-headers.tar.gz attempt 1 failed with ECONNRESET\n' +
+          'gyp http 200 https://nodejs.org/download/release/v24.12.0/node-v24.12.0-headers.tar.gz\n' +
+          'gyp ERR! build error\ngyp ERR! stack Error: `make` failed with exit code: 2'
+      )
+    ).toBe(false)
+    // A mirror answering non-2xx is a FetchError without a network code: a different remedy.
+    expect(
+      isNodeHeadersDownloadFailure(
+        'gyp ERR! configure error\ngyp ERR! stack FetchError: 404 Not Found https://mirror/dist/v24.12.0/node-v24.12.0-headers.tar.gz'
+      )
+    ).toBe(false)
   })
 })
 
 describe('formatNodeHeadersDownloadError', () => {
   it('names both host remedies when the host ships no headers', () => {
     const msg = formatNodeHeadersDownloadError(HEADERS_REFUSED, null)
-    expect(msg).toContain('does not ship them locally')
+    expect(msg).toContain('no local headers matching its own version')
     expect(msg).toContain('<prefix>/include/node')
     expect(msg).toContain('nvm, fnm, volta, n')
     expect(msg).toContain('disturl')
@@ -176,7 +190,7 @@ describe('formatNodeHeadersDownloadError', () => {
     const msg = formatNodeHeadersDownloadError(HEADERS_REFUSED, '/usr/local')
     expect(msg).toContain('/usr/local/include/node')
     expect(msg).toContain('Orca defect')
-    expect(msg).not.toContain('does not ship them locally')
+    expect(msg).not.toContain('no local headers matching its own version')
     expect(msg).not.toContain('nvm, fnm, volta, n')
     expect(msg).toContain('ECONNREFUSED')
   })
diff --git a/src/main/ssh/ssh-relay-deploy.ts b/src/main/ssh/ssh-relay-deploy.ts
index 5b7d30ec829..5d8101361c6 100644
--- a/src/main/ssh/ssh-relay-deploy.ts
+++ b/src/main/ssh/ssh-relay-deploy.ts
@@ -1265,8 +1265,15 @@ async function installNativeDeps(
         throw err
       }
       signal?.throwIfAborted()
+      // Same diagnosis as the install catch: this fallback is non-fatal, so the log is the only
+      // place the offline-headers cause can reach anyone.
+      const rebuildMsg = (err as Error).message
       console.warn(
-        `[ssh-relay][NATIVE-DEPS-REBUILD-FAIL] npm rebuild native deps failed at ${remoteDir} (${platform}): ${(err as Error).message}`
+        `[ssh-relay][NATIVE-DEPS-REBUILD-FAIL] npm rebuild native deps failed at ${remoteDir} (${platform}): ${
+          platform.startsWith('linux') && isNodeHeadersDownloadFailure(rebuildMsg)
+            ? formatNodeHeadersDownloadError(rebuildMsg, localNodeHeadersFromOutput(rebuildMsg))
+            : rebuildMsg
+        }`
       )
     }
     signal?.throwIfAborted()
diff --git a/src/main/ssh/ssh-relay-native-deps-install-staged-upload.test.ts b/src/main/ssh/ssh-relay-native-deps-install-staged-upload.test.ts
index 5a691b69af4..d3894456d99 100644
--- a/src/main/ssh/ssh-relay-native-deps-install-staged-upload.test.ts
+++ b/src/main/ssh/ssh-relay-native-deps-install-staged-upload.test.ts
@@ -190,7 +190,7 @@ describe('installNativeDeps staged uploads', () => {
 
     const error = await deployAndLaunchRelay(conn).catch((e: Error) => e)
     expect((error as Error).message).toContain('could not download the Node.js headers')
-    expect((error as Error).message).toContain('does not ship them locally')
+    expect((error as Error).message).toContain('no local headers matching its own version')
     expect((error as Error).message).toContain('ECONNREFUSED')
     // A full toolchain: the toolchain probe must not run, and this is not a "build tools" error.
     expect((error as Error).message).not.toContain('build tools')
@@ -205,7 +205,7 @@ describe('installNativeDeps staged uploads', () => {
       makeExecResponses({
         npmInstall: {
           reject:
-            'Command "npm install" failed (exit 1): ORCA-NODE-HEADERS:/usr/local\nnpm error gyp http fetch GET https://nodejs.org/download/release/v24.12.0/node-v24.12.0-headers.tar.gz attempt 1 failed with ECONNREFUSED'
+            'Command "npm install" failed (exit 1): ORCA-NODE-HEADERS:/usr/local\nnpm error gyp http fetch GET https://nodejs.org/download/release/v24.12.0/node-v24.12.0-headers.tar.gz attempt 1 failed with ECONNREFUSED\nnpm error gyp ERR! configure error'
         }
       })
     )
@@ -213,7 +213,7 @@ describe('installNativeDeps staged uploads', () => {
     const error = await deployAndLaunchRelay(conn).catch((e: Error) => e)
     expect((error as Error).message).toContain('/usr/local/include/node')
     expect((error as Error).message).toContain('Orca defect')
-    expect((error as Error).message).not.toContain('does not ship them locally')
+    expect((error as Error).message).not.toContain('no local headers matching its own version')
   })
 
   it('promotes only after the first-install lock is acquired', async () => {
diff --git a/src/main/ssh/ssh-relay-node-headers.test.ts b/src/main/ssh/ssh-relay-node-headers.test.ts
index fa5b6ac00c9..81b49954a22 100644
--- a/src/main/ssh/ssh-relay-node-headers.test.ts
+++ b/src/main/ssh/ssh-relay-node-headers.test.ts
@@ -98,6 +98,26 @@ describe.skipIf(!POSIX)('exportLocalNodeHeadersPrefix', () => {
     expect(nodedir).toBe(dirname(dirname(process.execPath)))
   })
 
+  it('clears an inherited nodedir when the probe finds no matching headers', () => {
+    // A remote profile's stale nodedir must not survive past the version check.
+    const root = mkdtempSync(join(tmpdir(), 'orca-node-headers-'))
+    roots.push(root)
+    const copied = join(root, 'bin', 'node')
+    mkdirSync(dirname(copied), { recursive: true })
+    spawnSync('cp', [process.execPath, copied])
+    const script = `${exportLocalNodeHeadersPrefix(copied)}printf '%s|%s' "$npm_config_nodedir" "$npm_package_config_node_gyp_nodedir"`
+    const result = spawnSync('/bin/sh', ['-c', script], {
+      encoding: 'utf8',
+      env: {
+        ...process.env,
+        npm_config_nodedir: '/usr/stale-headers',
+        npm_package_config_node_gyp_nodedir: '/usr/stale-headers'
+      }
+    })
+    expect(result.status).toBe(0)
+    expect(result.stdout.split('\n').at(-1)).toBe('|')
+  })
+
   it('does not fail the command line when node itself cannot run', () => {
     const script = `${exportLocalNodeHeadersPrefix('/nonexistent/node')}echo "after:$npm_config_nodedir"`
     const result = spawnSync('/bin/sh', ['-c', script], { encoding: 'utf8' })
diff --git a/src/main/ssh/ssh-relay-node-headers.ts b/src/main/ssh/ssh-relay-node-headers.ts
index 30897ed2ef4..7f9f6721d70 100644
--- a/src/main/ssh/ssh-relay-node-headers.ts
+++ b/src/main/ssh/ssh-relay-node-headers.ts
@@ -49,8 +49,11 @@ export const LOCAL_NODE_HEADERS_MARKER_PREFIX = 'ORCA-NODE-HEADERS:'
  */
 export function exportLocalNodeHeadersPrefix(nodePath: string): string {
   const probe = `${shellEscape(nodePath)} -e ${shellEscape(LOCAL_NODE_HEADERS_PROBE_JS)} 2>/dev/null`
+  // Why the unset: a remote profile can already carry a nodedir (a stale distro header dir, an old
+  // ~/.npmrc). Left alone it would bypass the version check above and build a wrong-ABI binding.
   return (
     `${NODEDIR_SHELL_VAR}=$(${probe}); ` +
+    `unset npm_config_nodedir npm_package_config_node_gyp_nodedir; ` +
     `if [ -n "$${NODEDIR_SHELL_VAR}" ]; then ` +
     `export npm_config_nodedir="$${NODEDIR_SHELL_VAR}" npm_package_config_node_gyp_nodedir="$${NODEDIR_SHELL_VAR}"; ` +
     `fi; ` +
diff --git a/src/main/ssh/ssh-relay-offline-node-headers.docker.test.ts b/src/main/ssh/ssh-relay-offline-node-headers.docker.test.ts
index 7805cb9040c..db9e1a83502 100644
--- a/src/main/ssh/ssh-relay-offline-node-headers.docker.test.ts
+++ b/src/main/ssh/ssh-relay-offline-node-headers.docker.test.ts
@@ -11,6 +11,7 @@
 import { execFileSync, spawnSync } from 'node:child_process'
 import { randomUUID } from 'node:crypto'
 import { mkdtempSync, readFileSync, rmSync } from 'node:fs'
+import { connect } from 'node:net'
 import { tmpdir } from 'node:os'
 import { join } from 'node:path'
 import { afterAll, beforeAll, describe, expect, it, vi } from 'vitest'
@@ -45,7 +46,7 @@ function dockerExec(fixture: TargetFixture, command: string): string {
   return run('docker', ['exec', fixture.containerName, 'bash', '-lc', command], 60_000)
 }
 
-function startTarget(): TargetFixture {
+async function startTarget(): Promise<TargetFixture> {
   const image = `orca-review-offline-headers:${NODE_IMAGE.replace(/[^A-Za-z0-9_.-]/g, '-')}`
   run(
     'docker',
@@ -85,9 +86,35 @@ function startTarget(): TargetFixture {
     120_000
   )
   const port = Number(run('docker', ['port', containerName, '22/tcp']).split(':').at(-1))
+  // `docker run -d` returns before sshd binds; connect() against a closed port is a flake.
+  await waitForSshBanner(port)
   return { containerName, identityFile, port, tempDir }
 }
 
+/** Resolves once sshd answers with its banner on the mapped port, or throws after the deadline. */
+async function waitForSshBanner(port: number, deadlineMs = 60_000): Promise<void> {
+  const deadline = Date.now() + deadlineMs
+  for (;;) {
+    const gotBanner = await new Promise<boolean>((resolve) => {
+      const socket = connect({ host: TARGET_HOST, port })
+      const done = (value: boolean): void => {
+        socket.destroy()
+        resolve(value)
+      }
+      socket.setTimeout(2_000, () => done(false))
+      socket.once('data', (chunk) => done(chunk.toString('utf8').startsWith('SSH-')))
+      socket.once('error', () => done(false))
+    })
+    if (gotBanner) {
+      return
+    }
+    if (Date.now() > deadline) {
+      throw new Error(`sshd on port ${port} did not answer within ${deadlineMs / 1000}s`)
+    }
+    await new Promise((resolve) => setTimeout(resolve, 500))
+  }
+}
+
 function stopTarget(fixture: TargetFixture | null): void {
   if (!fixture) {
     return
@@ -115,8 +142,8 @@ describe.skipIf(!RUN_REVIEW_ORACLE)(
   () => {
     let fixture: TargetFixture | null = null
 
-    beforeAll(() => {
-      fixture = startTarget()
+    beforeAll(async () => {
+      fixture = await startTarget()
     }, 900_000)
 
     afterAll(() => {