diff --git a/matrixbot/commands.py b/matrixbot/commands.py
index 72b5c46..04817ab 100644
--- a/matrixbot/commands.py
+++ b/matrixbot/commands.py
@@ -1390,37 +1390,39 @@ async def _generate_hangman_word() -> dict | None:
         'Format: {"word": "example", "hint": "short category or hint"}'
     )
     user_msg = "Pick a common English word between 5 and 8 letters (lowercase letters only, no hyphens or spaces) and give a short hint."
-    try:
-        timeout = aiohttp.ClientTimeout(total=60)
-        async with aiohttp.ClientSession(timeout=timeout) as session:
-            async with session.post(
-                f"{OLLAMA_URL}/api/chat",
-                json={
-                    "model": ASK_MODEL,
-                    "stream": False,
-                    "messages": [
-                        {"role": "system", "content": system_msg},
-                        {"role": "user", "content": user_msg},
-                    ],
-                },
-            ) as response:
-                data = await response.json()
-                text = data.get("message", {}).get("content", "").strip()
-                if "```" in text:
-                    text = re.sub(r"```[a-z]*\n?", "", text).strip()
-                m = re.search(r"\{[^{}]+\}", text, re.DOTALL)
-                candidate = m.group(0) if m else text
-                try:
-                    parsed = json.loads(candidate)
-                except json.JSONDecodeError:
-                    logger.warning("hangman: JSON parse failed, raw: %.200s", text)
-                    parsed = {}
-                word = parsed.get("word", "").lower().strip()
-                hint = parsed.get("hint", "").strip()
-                if word.isalpha() and 5 <= len(word) <= 8 and hint:
-                    return {"word": word, "hint": hint}
-    except Exception as e:
-        logger.error(f"hangman word generation error: {e}", exc_info=True)
+    for attempt in range(2):
+        try:
+            timeout = aiohttp.ClientTimeout(total=60)
+            async with aiohttp.ClientSession(timeout=timeout) as session:
+                async with session.post(
+                    f"{OLLAMA_URL}/api/chat",
+                    json={
+                        "model": ASK_MODEL,
+                        "stream": False,
+                        "messages": [
+                            {"role": "system", "content": system_msg},
+                            {"role": "user", "content": user_msg},
+                        ],
+                    },
+                ) as response:
+                    data = await response.json()
+                    text = data.get("message", {}).get("content", "").strip()
+                    if "```" in text:
+                        text = re.sub(r"```[a-z]*\n?", "", text).strip()
+                    m = re.search(r"\{[^{}]+\}", text, re.DOTALL)
+                    candidate = m.group(0) if m else text
+                    try:
+                        parsed = json.loads(candidate)
+                    except json.JSONDecodeError:
+                        logger.warning("hangman: JSON parse failed (attempt %d), raw: %.200s", attempt + 1, text)
+                        parsed = {}
+                    word = parsed.get("word", "").lower().strip()
+                    hint = parsed.get("hint", "").strip()
+                    if word.isalpha() and 5 <= len(word) <= 8 and hint:
+                        return {"word": word, "hint": hint}
+                    logger.warning("hangman: validation failed (attempt %d): word=%r hint=%r", attempt + 1, word, hint)
+        except Exception as e:
+            logger.error(f"hangman word generation error (attempt {attempt + 1}): {e}", exc_info=True)
     return None