diff --git a/messages/de.json b/messages/de.json
index 39cb35622..f069f25de 100644
--- a/messages/de.json
+++ b/messages/de.json
@@ -3257,6 +3257,7 @@
       "testProvider": "Aktiven Provider testen",
       "testSuccess": "OK — {provider} ({model})",
       "testFailedShort": "Test fehlgeschlagen: {message}",
+      "testUnexpectedResponse": "Verbindung zum KI-Anbieter fehlgeschlagen — unerwartete Antwort vom Server.",
       "disableCoach": {
         "title": "Coach ausblenden",
         "description": "Versteckt den Coach-Button und das Coach-Panel auf allen Seiten.",
diff --git a/messages/en.json b/messages/en.json
index e0b030cfd..1160ba975 100644
--- a/messages/en.json
+++ b/messages/en.json
@@ -3257,6 +3257,7 @@
       "testProvider": "Test active provider",
       "testSuccess": "OK — {provider} ({model})",
       "testFailedShort": "Test failed: {message}",
+      "testUnexpectedResponse": "AI provider connection failed — unexpected response from the server.",
       "disableCoach": {
         "title": "Hide Coach",
         "description": "Hides the Coach button and drawer everywhere.",
diff --git a/messages/es.json b/messages/es.json
index 80d51e25d..8c0b10aaf 100644
--- a/messages/es.json
+++ b/messages/es.json
@@ -3257,6 +3257,7 @@
       "testProvider": "Test active provider",
       "testSuccess": "OK — {provider} ({model})",
       "testFailedShort": "Test failed: {message}",
+      "testUnexpectedResponse": "AI provider connection failed — unexpected response from the server.",
       "disableCoach": {
         "title": "Ocultar el Coach",
         "description": "Oculta el botón del Coach y el panel en todas las páginas.",
diff --git a/messages/fr.json b/messages/fr.json
index 98d3ff977..b0f7ed8ca 100644
--- a/messages/fr.json
+++ b/messages/fr.json
@@ -3257,6 +3257,7 @@
       "testProvider": "Test active provider",
       "testSuccess": "OK — {provider} ({model})",
       "testFailedShort": "Test failed: {message}",
+      "testUnexpectedResponse": "AI provider connection failed — unexpected response from the server.",
       "disableCoach": {
         "title": "Masquer le Coach",
         "description": "Masque le bouton et le panneau du Coach sur toutes les pages.",
diff --git a/messages/it.json b/messages/it.json
index cd63d35b7..39c72189e 100644
--- a/messages/it.json
+++ b/messages/it.json
@@ -3257,6 +3257,7 @@
       "testProvider": "Test active provider",
       "testSuccess": "OK — {provider} ({model})",
       "testFailedShort": "Test failed: {message}",
+      "testUnexpectedResponse": "AI provider connection failed — unexpected response from the server.",
       "disableCoach": {
         "title": "Nascondi il Coach",
         "description": "Nasconde il pulsante e il pannello del Coach su tutte le pagine.",
diff --git a/messages/pl.json b/messages/pl.json
index 3b1a05642..f2b500f4c 100644
--- a/messages/pl.json
+++ b/messages/pl.json
@@ -3257,6 +3257,7 @@
       "testProvider": "Test active provider",
       "testSuccess": "OK — {provider} ({model})",
       "testFailedShort": "Test failed: {message}",
+      "testUnexpectedResponse": "AI provider connection failed — unexpected response from the server.",
       "disableCoach": {
         "title": "Ukryj Coacha",
         "description": "Ukrywa przycisk Coacha i panel na wszystkich stronach.",
diff --git a/src/components/settings/ai-section.tsx b/src/components/settings/ai-section.tsx
index 4326312ea..eb1902b66 100644
--- a/src/components/settings/ai-section.tsx
+++ b/src/components/settings/ai-section.tsx
@@ -1736,7 +1736,33 @@ function RuntimeActionsRow({
     setTestMsg(null);
     try {
       const res = await fetch("/api/ai/test", { method: "POST" });
-      const json = await res.json();
+      // Guard against a non-JSON body. A reverse proxy / Cloudflare can
+      // rewrite an origin error to its own HTML page; parsing that as JSON
+      // throws `Unexpected token '<'` (Safari: "did not match the
+      // expected pattern"). Show a clean message instead of leaking that.
+      const contentType = res.headers.get("content-type") ?? "";
+      if (!contentType.includes("application/json")) {
+        setTestOk(false);
+        setTestMsg(t("settings.ai.testUnexpectedResponse"));
+        return;
+      }
+      let json: {
+        data?: {
+          ok?: boolean;
+          providerType?: string;
+          model?: string;
+          reason?: string;
+        } | null;
+        error?: string | null;
+      };
+      try {
+        json = await res.json();
+      } catch {
+        setTestOk(false);
+        setTestMsg(t("settings.ai.testUnexpectedResponse"));
+        return;
+      }
+      // 4xx config errors still arrive via the error envelope.
       if (!res.ok) {
         setTestOk(false);
         setTestMsg(
@@ -1746,11 +1772,22 @@ function RuntimeActionsRow({
         );
         return;
       }
+      // Provider-call failures now arrive as 200 + { ok:false, reason }
+      // so the body is never rewritten by a proxy. Show the reason
+      // verbatim — it is a categorised, secret-free string.
+      if (json.data && json.data.ok === false) {
+        setTestOk(false);
+        setTestMsg(
+          json.data.reason ??
+            t("settings.ai.testFailedShort", { message: `HTTP ${res.status}` }),
+        );
+        return;
+      }
       setTestOk(true);
       setTestMsg(
         t("settings.ai.testSuccess", {
-          provider: json.data.providerType,
-          model: json.data.model,
+          provider: json.data?.providerType ?? "",
+          model: json.data?.model ?? "",
         }),
       );
     } catch (e) {
@@ -1774,7 +1811,27 @@ function RuntimeActionsRow({
         headers: { "Content-Type": "application/json" },
         body: JSON.stringify({ force: true }),
       });
-      const json = await res.json();
+      // Same defensive guard as the connection test: a proxy can rewrite
+      // a 5xx (e.g. all-providers-failed) to an HTML page, which would
+      // crash `res.json()` with `Unexpected token '<'`.
+      const contentType = res.headers.get("content-type") ?? "";
+      if (!contentType.includes("application/json")) {
+        setRegenOk(false);
+        setRegenMsg(
+          res.status === 429
+            ? t("settings.regenerateRateLimit")
+            : t("settings.ai.testUnexpectedResponse"),
+        );
+        return;
+      }
+      let json: { error?: string | null };
+      try {
+        json = await res.json();
+      } catch {
+        setRegenOk(false);
+        setRegenMsg(t("settings.ai.testUnexpectedResponse"));
+        return;
+      }
       if (!res.ok) {
         setRegenOk(false);
         setRegenMsg(