diff --git a/CLAUDE.md b/CLAUDE.md
index fba33e0..b63ed4c 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -671,6 +671,11 @@ LLAMA_SWAP_TTS_REQUEST_TIMEOUT_SECONDS=600     # Per-request synth timeout (long
 
 # Insight Chat Continuation
 AGENTIC_CHAT_MAX_ITERATIONS=6                  # Cap on tool-calling iterations per chat turn (default 6)
+AGENTIC_CHAT_DEFAULT_NUM_CTX=32768             # Assumed context window for the history-truncation budget
+                                               # when a chat request omits num_ctx (default 32768). Size to
+                                               # the smallest context among the chat models actually served;
+                                               # too small silently guts replayed history every turn (and
+                                               # destroys llama.cpp KV-cache prefix reuse).
 ```
 
 **AI Insights Fallback Behavior:**
@@ -794,14 +799,17 @@ Per-`(library_id, file_path)` async mutex (`AppState.insight_chat.chat_locks`)
 serialises concurrent turns on the same insight so the JSON blob doesn't race.
 
 Context management is a soft bound: if the serialized history exceeds
-`num_ctx - 2048` tokens (cheap 4-byte/token heuristic), the oldest
-assistant-tool_call + tool_result pairs are dropped until under budget. The
+`num_ctx - 2048` tokens (cheap 4-byte/token heuristic; `num_ctx` defaults
+to `AGENTIC_CHAT_DEFAULT_NUM_CTX`, 32768, when the request omits it), the
+oldest assistant-tool_call + tool_result pairs are dropped until under budget. The
 initial user message (with any images) and system prompt are always preserved.
 The `truncated` event / flag is surfaced to the client when a drop occurred.
 
 Configurable env:
 - `AGENTIC_CHAT_MAX_ITERATIONS` — cap on tool-calling iterations per turn
   (default 6). Per-request `max_iterations` is clamped to this cap.
+- `AGENTIC_CHAT_DEFAULT_NUM_CTX` — assumed context window for the truncation
+  budget when the request omits `num_ctx` (default 32768).
 
 **Apollo Places integration (optional):**
 
diff --git a/src/ai/insight_chat.rs b/src/ai/insight_chat.rs
index 7298296..84f2b32 100644
--- a/src/ai/insight_chat.rs
+++ b/src/ai/insight_chat.rs
@@ -19,7 +19,13 @@ use futures::stream::{BoxStream, StreamExt};
 use uuid::Uuid;
 
 const DEFAULT_MAX_ITERATIONS: usize = 6;
-const DEFAULT_NUM_CTX: i32 = 8192;
+/// Assumed context window when the request doesn't specify `num_ctx`.
+/// The llama-swap chat slots serve 20k-131k contexts and real conversations
+/// rarely pass ~16k tokens, so 32k keeps the truncation pass from gutting
+/// history that the server could comfortably hold (which also destroys the
+/// server's KV-cache prefix reuse). Override per-deploy with
+/// AGENTIC_CHAT_DEFAULT_NUM_CTX if the serving models change shape.
+const DEFAULT_NUM_CTX: i32 = 32768;
 /// Headroom reserved for the model's response, deducted from the context
 /// budget when deciding whether to truncate the replayed history.
 const RESPONSE_HEADROOM_TOKENS: usize = 2048;
@@ -367,7 +373,7 @@ impl InsightChatService {
 
         // 6. Apply truncation budget. Drops oldest tool_call+tool pairs
         //    (preserves system + first user including any images).
-        let budget_tokens = (req.num_ctx.unwrap_or(DEFAULT_NUM_CTX) as usize)
+        let budget_tokens = (req.num_ctx.unwrap_or_else(env_default_num_ctx) as usize)
             .saturating_sub(RESPONSE_HEADROOM_TOKENS);
         let budget_bytes = budget_tokens.saturating_mul(BYTES_PER_TOKEN);
         let truncated = apply_context_budget(&mut messages, budget_bytes);
@@ -864,7 +870,7 @@ impl InsightChatService {
             None
         };
 
-        let budget_tokens = (req.num_ctx.unwrap_or(DEFAULT_NUM_CTX) as usize)
+        let budget_tokens = (req.num_ctx.unwrap_or_else(env_default_num_ctx) as usize)
             .saturating_sub(RESPONSE_HEADROOM_TOKENS);
         let budget_bytes = budget_tokens.saturating_mul(BYTES_PER_TOKEN);
         let truncated = apply_context_budget(&mut messages, budget_bytes);
@@ -1446,7 +1452,7 @@ impl InsightChatService {
         };
 
         // Truncate before appending the new user turn.
-        let budget_tokens = (req.num_ctx.unwrap_or(DEFAULT_NUM_CTX) as usize)
+        let budget_tokens = (req.num_ctx.unwrap_or_else(env_default_num_ctx) as usize)
             .saturating_sub(RESPONSE_HEADROOM_TOKENS);
         let budget_bytes = budget_tokens.saturating_mul(BYTES_PER_TOKEN);
         let truncated = apply_context_budget(&mut messages, budget_bytes);
@@ -2191,6 +2197,17 @@ fn env_max_iterations() -> usize {
         .max(1)
 }
 
+/// Read AGENTIC_CHAT_DEFAULT_NUM_CTX once per call — the assumed context
+/// window for the truncation budget when the request omits `num_ctx`. Same
+/// no-static-global rationale as `env_max_iterations` above.
+fn env_default_num_ctx() -> i32 {
+    std::env::var("AGENTIC_CHAT_DEFAULT_NUM_CTX")
+        .ok()
+        .and_then(|s| s.parse::<i32>().ok())
+        .unwrap_or(DEFAULT_NUM_CTX)
+        .max(RESPONSE_HEADROOM_TOKENS as i32 + 1024)
+}
+
 /// Append a per-turn iteration-budget reminder to the replayed system
 /// message so the model knows how many tool-calling rounds this turn gets.
 /// Returns the original `content` so the caller can restore it before
@@ -2516,8 +2533,8 @@ mod tests {
             assistant_text("here is the answer"),
         ];
 
-        // Default budget: (8192 - 2048) * 4 bytes ≈ 24KB. The text easily fits;
-        // only the (excluded) image bytes could blow it.
+        // Default budget: (32768 - 2048) * 4 bytes ≈ 120KB. The text easily
+        // fits; only the (excluded) image bytes could blow it.
         let budget_bytes = (DEFAULT_NUM_CTX as usize - RESPONSE_HEADROOM_TOKENS) * BYTES_PER_TOKEN;
         let original_len = msgs.len();
         let dropped = apply_context_budget(&mut msgs, budget_bytes);