diff --git a/backend/Dockerfile b/backend/Dockerfile
index 4909e4e..081d0dd 100644
--- a/backend/Dockerfile
+++ b/backend/Dockerfile
@@ -14,7 +14,8 @@ ENV NODE_ENV=production
 # native modules (better-sqlite3, ssh2, node-pty) compile from source on install.
 # openssh-client provides the `ssh` binary, which node-pty shells out to for
 # certificate-based auth (ssh2 has no OpenSSH certificate support).
-RUN apk add --no-cache python3 make g++ openssh-client
+# iputils provides `ping`, used by the mesh-gate reachability check.
+RUN apk add --no-cache python3 make g++ openssh-client iputils
 COPY package.json package-lock.json* ./
 RUN npm install --omit=dev
 COPY --from=build /app/dist ./dist
diff --git a/backend/src/routes/system.ts b/backend/src/routes/system.ts
index f2e9fa7..626132e 100644
--- a/backend/src/routes/system.ts
+++ b/backend/src/routes/system.ts
@@ -1,8 +1,12 @@
 import type { FastifyInstance } from 'fastify'
 import { networkInterfaces } from 'node:os'
+import { execFile } from 'node:child_process'
+import { promisify } from 'node:util'
 import { z } from 'zod'
 import { getConfig, setConfig, logEvent } from '../db/index.js'
 
+const execFileAsync = promisify(execFile)
+
 /** Parses "a.b.c.d/n" into a 32-bit base int + prefix length. */
 function parseCidr(cidr: string): { base: number; prefix: number } | null {
   const match = /^(\d{1,3})\.(\d{1,3})\.(\d{1,3})\.(\d{1,3})\/(\d{1,2})$/.exec(cidr.trim())
@@ -20,37 +24,57 @@ function ipToInt(ip: string): number | null {
   return (parts[0]! << 24) | (parts[1]! << 16) | (parts[2]! << 8) | parts[3]!
 }
 
+function ipInCidr(ip: string, cidr: { base: number; prefix: number }): boolean {
+  const mask = cidr.prefix === 0 ? 0 : (-1 << (32 - cidr.prefix)) >>> 0
+  const ipInt = ipToInt(ip)
+  if (ipInt === null) return false
+  return ((ipInt & mask) >>> 0) === ((cidr.base & mask) >>> 0)
+}
+
 /** Finds this host's own IPv4 address that falls within the given mesh CIDR, if any. */
 function findHostIpInCidr(cidr: { base: number; prefix: number }): string | null {
-  const mask = cidr.prefix === 0 ? 0 : (-1 << (32 - cidr.prefix)) >>> 0
   for (const addrs of Object.values(networkInterfaces())) {
     for (const addr of addrs ?? []) {
-      if (addr.family !== 'IPv4') continue
-      const ipInt = ipToInt(addr.address)
-      if (ipInt === null) continue
-      if (((ipInt & mask) >>> 0) === ((cidr.base & mask) >>> 0)) return addr.address
+      if (addr.family === 'IPv4' && ipInCidr(addr.address, cidr)) return addr.address
     }
   }
   return null
 }
 
+/**
+ * Some meshes are routed rather than locally-addressed — e.g. a VPC peered into a
+ * NetBird mesh, where this host keeps its own 192.x address but can still reach mesh
+ * peers (100.x) through routing. In that case there's no local mesh IP to find, so we
+ * fall back to pinging an admin-supplied peer/gateway IP that's known to be on the mesh.
+ */
+async function canReachIp(ip: string): Promise<boolean> {
+  try {
+    await execFileAsync('ping', ['-c', '1', '-W', '2', ip])
+    return true
+  } catch {
+    return false
+  }
+}
+
 function meshStatusPayload() {
   const required = getConfig('mesh.required') === 'true'
   const cidr = getConfig('mesh.cidr') ?? null
   const verifiedAt = getConfig('mesh.verifiedAt')
+  const verifiedVia = getConfig('mesh.verifiedVia') ?? null
   const overridden = getConfig('mesh.overrideUntil') === 'permanent'
   const parsed = cidr ? parseCidr(cidr) : null
   return {
     required,
     verified: !!verifiedAt,
     verifiedAt: verifiedAt ?? null,
+    verifiedVia,
     overridden,
     cidr,
     hostMeshIp: parsed ? findHostIpInCidr(parsed) : null,
   }
 }
 
-const verifySchema = z.object({ cidr: z.string().min(1) })
+const verifySchema = z.object({ cidr: z.string().min(1), testIp: z.string().min(1).optional() })
 
 export async function systemRoutes(app: FastifyInstance) {
   app.get('/api/system/mesh-status', { onRequest: [app.authenticate] }, async () => {
@@ -58,8 +82,9 @@ export async function systemRoutes(app: FastifyInstance) {
   })
 
   // Verification is mesh-tech-agnostic: any overlay network (NetBird, WireGuard,
-  // ZeroTier, Tailscale...) assigns this host an IP in its own range. We just check
-  // the host has an address inside the admin-supplied CIDR — no vendor API needed.
+  // ZeroTier, Tailscale...) assigns this host an IP in its own range — checked first.
+  // If this host doesn't hold a local mesh IP (e.g. a VPC routed into the mesh), fall
+  // back to pinging an admin-supplied peer/gateway IP known to be on the mesh.
   app.post('/api/system/mesh/verify', { onRequest: [app.requireAdmin] }, async (req, reply) => {
     const parsed = verifySchema.safeParse(req.body)
     if (!parsed.success) {
@@ -71,18 +96,31 @@ export async function systemRoutes(app: FastifyInstance) {
     const hostMeshIp = findHostIpInCidr(cidr)
     setConfig('mesh.cidr', parsed.data.cidr)
 
-    if (hostMeshIp) {
-      setConfig('mesh.verifiedAt', new Date().toISOString())
-      logEvent('mesh_verified', `Mesh verified — host has ${hostMeshIp} in ${parsed.data.cidr}`)
-    } else {
-      logEvent('mesh_verify_failed', `Mesh verification failed — no host IP found in ${parsed.data.cidr}`)
+    let ok = !!hostMeshIp
+    let message = hostMeshIp ? `Host is on the mesh (${hostMeshIp})` : 'No host IP found in that range'
+    let via: 'local-ip' | 'reachable' | null = hostMeshIp ? 'local-ip' : null
+
+    if (!ok && parsed.data.testIp) {
+      if (!ipInCidr(parsed.data.testIp, cidr)) {
+        return reply.code(400).send({ error: 'Test IP is not inside the given CIDR' })
+      }
+      const reachable = await canReachIp(parsed.data.testIp)
+      ok = reachable
+      via = reachable ? 'reachable' : null
+      message = reachable
+        ? `Host can reach ${parsed.data.testIp} on the mesh`
+        : `Host has no local mesh IP and could not reach ${parsed.data.testIp}`
     }
 
-    return {
-      ok: !!hostMeshIp,
-      message: hostMeshIp ? `Host is on the mesh (${hostMeshIp})` : 'No host IP found in that range',
-      hostMeshIp,
+    if (ok) {
+      setConfig('mesh.verifiedAt', new Date().toISOString())
+      setConfig('mesh.verifiedVia', via ?? 'local-ip')
+      logEvent('mesh_verified', `Mesh verified (${via}) — ${message}`)
+    } else {
+      logEvent('mesh_verify_failed', `Mesh verification failed: ${message}`)
     }
+
+    return { ok, message, hostMeshIp }
   })
 
   app.post('/api/system/mesh/override', { onRequest: [app.requireAdmin] }, async (req) => {
diff --git a/src/lib/api.ts b/src/lib/api.ts
index 5985007..d945e03 100644
--- a/src/lib/api.ts
+++ b/src/lib/api.ts
@@ -59,10 +59,10 @@ export const api = {
   listLoginEvents: (limit = 20) => apiFetch<{ events: LoginEvent[] }>(`/auth/login-events?limit=${limit}`),
 
   getMeshStatus: () => apiFetch<MeshStatus>('/system/mesh-status'),
-  verifyMesh: (cidr: string) =>
+  verifyMesh: (cidr: string, testIp?: string) =>
     apiFetch<{ ok: boolean; message: string; hostMeshIp: string | null }>('/system/mesh/verify', {
       method: 'POST',
-      body: JSON.stringify({ cidr }),
+      body: JSON.stringify({ cidr, testIp }),
     }),
   overrideMesh: () => apiFetch<MeshStatus>('/system/mesh/override', { method: 'POST' }),
   setMeshRequired: (required: boolean) =>
@@ -251,6 +251,7 @@ export interface MeshStatus {
   required: boolean
   verified: boolean
   verifiedAt: string | null
+  verifiedVia: 'local-ip' | 'reachable' | null
   overridden: boolean
   cidr: string | null
   hostMeshIp: string | null
diff --git a/src/pages/MeshGate.tsx b/src/pages/MeshGate.tsx
index 7bd0e4f..87fae76 100644
--- a/src/pages/MeshGate.tsx
+++ b/src/pages/MeshGate.tsx
@@ -44,6 +44,7 @@ const goldButton: React.CSSProperties = {
 export default function MeshGate() {
   const { refreshMeshStatus } = useAuth()
   const [cidr, setCidr] = useState('')
+  const [testIp, setTestIp] = useState('')
   const [error, setError] = useState<string | null>(null)
   const [testResult, setTestResult] = useState<{ ok: boolean; message: string; hostMeshIp: string | null } | null>(null)
   const [submitting, setSubmitting] = useState(false)
@@ -55,7 +56,7 @@ export default function MeshGate() {
     setTestResult(null)
     setSubmitting(true)
     try {
-      const result = await api.verifyMesh(cidr)
+      const result = await api.verifyMesh(cidr, testIp || undefined)
       setTestResult(result)
       if (result.ok) await refreshMeshStatus()
     } catch (err) {
@@ -110,6 +111,19 @@ export default function MeshGate() {
             required
           />
 
+          <label style={{ ...fieldLabel, marginTop: '14px' }}>Peer/Gateway IP on the mesh (optional)</label>
+          <input
+            style={fieldInput}
+            value={testIp}
+            onChange={(e) => setTestIp(e.target.value)}
+            placeholder="e.g. 100.64.0.1 — only needed if this host's own IP isn't in the mesh range"
+          />
+          <p style={{ fontSize: '10px', color: '#5C5F66', marginTop: '6px' }}>
+            If this host reaches the mesh through routing instead of holding a local mesh IP
+            (e.g. a VPC peered into the mesh), give us an address on the mesh we can ping to confirm
+            reachability.
+          </p>
+
           {error && <p style={{ fontSize: '12px', color: '#E74C3C', marginTop: '12px' }}>{error}</p>}
           {testResult && (
             <p style={{ fontSize: '12px', color: testResult.ok ? '#2ECC71' : '#E74C3C', marginTop: '12px' }}>