diff --git a/matrixbot/commands.py b/matrixbot/commands.py
index 49410ee..a548e2a 100644
--- a/matrixbot/commands.py
+++ b/matrixbot/commands.py
@@ -937,7 +937,7 @@ async def _generate_trivia_question(category: str) -> dict | None:
         "The question should be clear, factual, and have exactly one correct answer."
     )
     try:
-        timeout = aiohttp.ClientTimeout(total=20)
+        timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
             async with session.post(
                 f"{OLLAMA_URL}/api/chat",
@@ -1237,7 +1237,7 @@ async def _generate_hangman_word() -> dict | None:
     )
     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=20)
+        timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
             async with session.post(
                 f"{OLLAMA_URL}/api/chat",
@@ -1444,7 +1444,7 @@ async def _generate_scramble_word() -> dict | None:
     )
     user_msg = "Pick a common English word between 4 and 8 letters (lowercase letters only, no hyphens or spaces)."
     try:
-        timeout = aiohttp.ClientTimeout(total=20)
+        timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
             async with session.post(
                 f"{OLLAMA_URL}/api/chat",
@@ -1566,7 +1566,7 @@ async def _generate_wyr() -> dict | None:
     )
     user_msg = "Generate a fun, creative Would You Rather question. Keep each option under 10 words."
     try:
-        timeout = aiohttp.ClientTimeout(total=20)
+        timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
             async with session.post(
                 f"{OLLAMA_URL}/api/chat",
@@ -1664,7 +1664,7 @@ async def _generate_riddle() -> dict | None:
     )
     user_msg = "Generate a clever riddle. The answer should be 1-4 words."
     try:
-        timeout = aiohttp.ClientTimeout(total=20)
+        timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
             async with session.post(
                 f"{OLLAMA_URL}/api/chat",
@@ -1876,7 +1876,7 @@ async def _generate_story_opener() -> str | None:
         "Just the opening sentence, no explanation or title."
     )
     try:
-        timeout = aiohttp.ClientTimeout(total=20)
+        timeout = aiohttp.ClientTimeout(total=60)
         async with aiohttp.ClientSession(timeout=timeout) as session:
             async with session.post(
                 f"{OLLAMA_URL}/api/generate",