diff --git a/src/fabledassistant/app.py b/src/fabledassistant/app.py
index 985d56e..3e5d07c 100644
--- a/src/fabledassistant/app.py
+++ b/src/fabledassistant/app.py
@@ -183,16 +183,18 @@ def create_app() -> Quart:
             """Send a minimal chat request to prime Ollama's KV cache with the user's system prompt.
 
             This ensures the next real user message only needs to process its own tokens
-            rather than the full ~5,600-token system prompt, cutting TTFT from ~25s to <1s.
+            rather than the full ~4,650-token system prompt, cutting TTFT from ~25s to <1s.
+            The num_ctx must match what real requests will use so Ollama doesn't reload.
             """
             try:
-                from fabledassistant.services.llm import build_context
+                from fabledassistant.services.llm import build_context, pick_num_ctx
                 messages, _ = await build_context(
                     user_id=user_id,
                     history=[],
                     current_note_id=None,
                     user_message=" ",
                 )
+                num_ctx = pick_num_ctx(messages)
                 async with httpx.AsyncClient(timeout=120.0) as client:
                     await client.post(
                         f"{Config.OLLAMA_URL}/api/chat",
@@ -200,11 +202,11 @@ def create_app() -> Quart:
                             "model": model,
                             "messages": messages,
                             "stream": False,
-                            "options": {"num_predict": 1},
+                            "options": {"num_predict": 1, "num_ctx": num_ctx},
                             "keep_alive": "2h",
                         },
                     )
-                logger.info("Primed KV cache for user %d with model '%s'", user_id, model)
+                logger.info("Primed KV cache for user %d with model '%s' (num_ctx=%d)", user_id, model, num_ctx)
             except Exception:
                 logger.warning("Failed to prime KV cache for user %d", user_id, exc_info=True)
 
diff --git a/src/fabledassistant/routes/settings.py b/src/fabledassistant/routes/settings.py
index a180fb2..979075e 100644
--- a/src/fabledassistant/routes/settings.py
+++ b/src/fabledassistant/routes/settings.py
@@ -15,7 +15,7 @@ logger = logging.getLogger(__name__)
 async def _prime_kv_cache_bg(user_id: int, model: str) -> None:
     """Fire-and-forget: prime Ollama's KV cache with the user's system prompt."""
     import httpx
-    from fabledassistant.services.llm import build_context
+    from fabledassistant.services.llm import build_context, pick_num_ctx
     try:
         messages, _ = await build_context(
             user_id=user_id,
@@ -23,6 +23,7 @@ async def _prime_kv_cache_bg(user_id: int, model: str) -> None:
             current_note_id=None,
             user_message=" ",
         )
+        num_ctx = pick_num_ctx(messages)
         async with httpx.AsyncClient(timeout=120.0) as client:
             await client.post(
                 f"{Config.OLLAMA_URL}/api/chat",
@@ -30,11 +31,11 @@ async def _prime_kv_cache_bg(user_id: int, model: str) -> None:
                     "model": model,
                     "messages": messages,
                     "stream": False,
-                    "options": {"num_predict": 1},
+                    "options": {"num_predict": 1, "num_ctx": num_ctx},
                     "keep_alive": "2h",
                 },
             )
-        logger.info("Primed KV cache for user %d with model '%s'", user_id, model)
+        logger.info("Primed KV cache for user %d with model '%s' (num_ctx=%d)", user_id, model, num_ctx)
     except Exception:
         logger.warning("Failed to prime KV cache for user %d", user_id, exc_info=True)
 
diff --git a/src/fabledassistant/services/generation_task.py b/src/fabledassistant/services/generation_task.py
index f757b97..048fafd 100644
--- a/src/fabledassistant/services/generation_task.py
+++ b/src/fabledassistant/services/generation_task.py
@@ -22,7 +22,7 @@ from fabledassistant.services.generation_buffer import (
     GenerationBuffer,
     GenerationState,
 )
-from fabledassistant.services.llm import ChatChunk, build_context, generate_completion, stream_chat, stream_chat_with_tools, summarize_history_for_context
+from fabledassistant.services.llm import ChatChunk, build_context, generate_completion, pick_num_ctx, stream_chat, stream_chat_with_tools, summarize_history_for_context
 from fabledassistant.services.chat import update_conversation_title
 from fabledassistant.services.settings import get_setting
 from fabledassistant.services.logging import log_generation
@@ -168,6 +168,7 @@ async def _stream_with_retry(
     model: str,
     tools: list[dict],
     think: bool,
+    num_ctx: int | None = None,
 ) -> AsyncGenerator[ChatChunk, None]:
     """stream_chat_with_tools with automatic retry on Ollama 500 errors.
 
@@ -184,7 +185,7 @@ async def _stream_with_retry(
             )
             await asyncio.sleep(delay)
         try:
-            async for chunk in stream_chat_with_tools(messages, model, tools=tools, think=think):
+            async for chunk in stream_chat_with_tools(messages, model, tools=tools, think=think, num_ctx=num_ctx):
                 yield chunk
             return
         except httpx.HTTPStatusError as exc:
@@ -260,6 +261,11 @@ async def run_generation(
         voice_speech_style=voice_speech_style,
     )
 
+    # Pick the smallest context tier that fits the current messages.
+    # Using the minimum needed tier reduces KV cache size and speeds up prefill.
+    num_ctx = pick_num_ctx(messages)
+    logger.debug("Adaptive num_ctx=%d for conv %d", num_ctx, conv_id)
+
     # Emit context event
     buf.append_event("context", {"context": context_meta})
 
@@ -269,6 +275,7 @@ async def run_generation(
     t_start = time.monotonic()
     timing: dict = {
         "think": think,
+        "num_ctx": num_ctx,
         "tools": [],
         "rounds": 0,
         "prompt_tokens": None,
@@ -298,7 +305,7 @@ async def run_generation(
             buf.append_event("status", {"status": "Generating response..." if _round == 0 else "Composing response..."})
             t_stream = time.monotonic()
 
-            async for chunk in _stream_with_retry(messages, model, tools, think):
+            async for chunk in _stream_with_retry(messages, model, tools, think, num_ctx=num_ctx):
                 if buf.cancel_event.is_set():
                     cancelled = True
                     break
@@ -535,7 +542,7 @@ async def run_assist_generation(
             await asyncio.sleep(delay)
         try:
             buf.content_so_far = ""
-            async for chunk in stream_chat(messages, model, options={"num_predict": Config.OLLAMA_NUM_CTX}):
+            async for chunk in stream_chat(messages, model, options={"num_predict": num_ctx}, num_ctx=num_ctx):
                 buf.content_so_far += chunk
                 buf.append_event("chunk", {"chunk": chunk})
 
diff --git a/src/fabledassistant/services/llm.py b/src/fabledassistant/services/llm.py
index fdb924c..67abd71 100644
--- a/src/fabledassistant/services/llm.py
+++ b/src/fabledassistant/services/llm.py
@@ -19,6 +19,28 @@ from fabledassistant.services.settings import get_setting
 
 logger = logging.getLogger(__name__)
 
+# Context window tiers. The smallest tier that fits the current input is used
+# so Ollama allocates a smaller KV cache, reducing prefill time and VRAM usage.
+# Requests using the same tier hit Ollama's prefix cache; a tier upgrade causes
+# a one-time model reload but then the larger cache stays warm.
+_CTX_TIERS = (8192, 16384, 32768)
+
+
+def pick_num_ctx(messages: list[dict]) -> int:
+    """Return the smallest context tier that fits *messages* with 25% headroom.
+
+    Stays at or below Config.OLLAMA_NUM_CTX (the configured ceiling).
+    """
+    total_chars = sum(len(m.get("content") or "") for m in messages)
+    estimated_tokens = int(total_chars / 3.5)
+    needed = int(estimated_tokens * 1.25) + 256  # 25% headroom + output buffer
+    cap = Config.OLLAMA_NUM_CTX
+    for tier in _CTX_TIERS:
+        if tier >= needed and tier <= cap:
+            return tier
+    return cap
+
+
 STOP_WORDS = frozenset({
     "a", "an", "the", "is", "it", "to", "in", "for", "of", "and", "or",
     "on", "at", "by", "with", "from", "as", "be", "was", "were", "been",
@@ -112,6 +134,7 @@ async def stream_chat(
     model: str,
     options: dict | None = None,
     think: bool = False,
+    num_ctx: int | None = None,
 ) -> AsyncGenerator[str, None]:
     """Stream chat completion from Ollama, yielding content chunks.
 
@@ -119,7 +142,7 @@ async def stream_chat(
     Thinking tokens are silently discarded anyway, but disabling avoids the
     multi-minute delay before the first content token arrives.
     """
-    merged_options = {"num_ctx": Config.OLLAMA_NUM_CTX}
+    merged_options = {"num_ctx": num_ctx or Config.OLLAMA_NUM_CTX}
     if options:
         merged_options.update(options)
     payload: dict = {"model": model, "messages": messages, "stream": True, "options": merged_options, "think": think, "keep_alive": "2h"}
@@ -159,6 +182,7 @@ async def stream_chat_with_tools(
     model: str,
     tools: list[dict] | None = None,
     think: bool = False,
+    num_ctx: int | None = None,
 ) -> AsyncGenerator[ChatChunk, None]:
     """Stream chat completion from Ollama with tool support.
 
@@ -170,7 +194,8 @@ async def stream_chat_with_tools(
     Thinking tokens are consumed by Ollama and not forwarded to the caller;
     only the final response content is yielded. Expect higher TTFT when enabled.
     """
-    options: dict = {"num_ctx": Config.OLLAMA_NUM_CTX}
+    resolved_ctx = num_ctx or Config.OLLAMA_NUM_CTX
+    options: dict = {"num_ctx": resolved_ctx}
     if tools:
         options["num_predict"] = 8192
     payload: dict = {