diff --git a/hypaware-core/plugins-workspace/ai-gateway/src/source.js b/hypaware-core/plugins-workspace/ai-gateway/src/source.js
index 94746945..154490aa 100644
--- a/hypaware-core/plugins-workspace/ai-gateway/src/source.js
+++ b/hypaware-core/plugins-workspace/ai-gateway/src/source.js
@@ -432,9 +432,14 @@ async function prepareInterception(ctx, config, upstreams, liveState) {
   if (!config.proxyMode) {
     // Proxy mode is off, but a CA on disk means a client was attached in proxy
     // mode at some point and may still have `HTTPS_PROXY` pointing here. Serve
-    // blind tunnels so its egress keeps working, and say so loudly: the repair
-    // is a re-attach (or a detach), and nothing else on the machine will
-    // volunteer that.
+    // blind tunnels so its egress keeps working, and say so loudly: nothing
+    // else on the machine will volunteer that this install is in the degraded
+    // state. A plain re-attach is NOT the remedy: attach leaves the CA where
+    // it is on purpose (the trust is offered back, never taken), so the file
+    // that puts the install in this state survives the re-attach. The
+    // remedies that land are removing the CA (`hyp detach claude --purge`,
+    // then re-attach) or turning `proxy_mode` back on.
+    // @ref LLP 0262#migration [constrained-by]: attach offers the CA back rather than removing it, so it cannot clear this state on its own
     const stale = await readLocalCaInfo({ stateRoot: defaultStateRoot(ctx.env) })
     if (stale) {
       liveState.interceptionError = 'proxy_mode is off but a local CA is installed'
@@ -442,7 +447,8 @@ async function prepareInterception(ctx, config, upstreams, liveState) {
         [Attr.PLUGIN]: PLUGIN_NAME,
         ca_cert_path: stale.certPath,
         reason: 'serving blind tunnels so an already-attached client keeps working; ' +
-          'run `hyp attach claude` to move it back to base-URL mode, or `hyp detach claude`',
+          're-attaching leaves this CA on disk, so run `hyp detach claude --purge` ' +
+          'and re-attach to clear the proxy residue, or turn proxy_mode back on',
       })
       return { tunnelOnly: true }
     }
diff --git a/test/plugins/ai-gateway-proxy-mode.test.js b/test/plugins/ai-gateway-proxy-mode.test.js
index 32839fa8..79b5b7e8 100644
--- a/test/plugins/ai-gateway-proxy-mode.test.js
+++ b/test/plugins/ai-gateway-proxy-mode.test.js
@@ -555,10 +555,13 @@ test('proxy mode turned off with a CA still installed serves blind tunnels', asy
   const echoPort = echoAddress && typeof echoAddress === 'object' ? echoAddress.port : 0
   t.after(() => new Promise((resolve) => echo.close(() => resolve(undefined))))
 
-  /** @type {{ level: string, event: string }[]} */
+  /** @type {{ level: string, event: string, attrs: Record<string, unknown> }[]} */
   const logged = []
   /** @param {string} level */
-  const record = (level) => (/** @type {string} */ event) => logged.push({ level, event })
+  const record = (level) => (
+    /** @type {string} */ event,
+    /** @type {Record<string, unknown> | undefined} */ attrs
+  ) => logged.push({ level, event, attrs: attrs ?? {} })
   const ctx = /** @type {any} */ ({
     // proxy_mode deliberately absent, as if the operator turned it back off.
     config: {
@@ -576,7 +579,17 @@ test('proxy mode turned off with a CA still installed serves blind tunnels', asy
   const details = /** @type {any} */ ((await source.status()).details)
   assert.equal(details.proxy_mode, false)
   assert.match(details.proxy_mode_error, /a local CA is installed/)
-  assert.equal(logged.some((l) => l.event === 'aigw.proxy_mode_stale_ca'), true)
+  const staleWarn = logged.find((l) => l.event === 'aigw.proxy_mode_stale_ca')
+  assert.ok(staleWarn, 'the stale-CA warning is emitted')
+
+  // The warning has to name a remedy that actually works. Attach deliberately
+  // leaves the CA on disk (it offers the trust back rather than taking it), so
+  // telling the operator to re-attach leaves the install exactly as degraded
+  // as it was, every time, until the CA is gone.
+  // @ref LLP 0262#migration [tests]: the stale-CA remedy cannot be a plain re-attach
+  const reason = String(staleWarn.attrs.reason ?? '')
+  assert.match(reason, /hyp detach claude --purge/)
+  assert.doesNotMatch(reason, /run `hyp attach claude` to move it back/)
 
   // The tunnel is still served, so an already-attached client keeps its egress
   // instead of losing all HTTPS. (The byte-level round trip is covered by