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//! History-shaping operations on [`ConversationHistory`]: trim under
//! token pressure, maintain the Anthropic cache anchor against the
//! 20-block lookback window, drop leading orphaned tool results so
//! the OpenAI Responses API doesn't reject the request, and build
//! the mechanical drop-summary used by [`Self::fallback_trim`] when
//! summarisation isn't available.
use crate::api::{Message, utils::truncate_at_char_boundary};
use crate::repl::conversation::ConversationHistory;
/// Hard floor on the number of messages [`ConversationHistory::trim_if_needed`]
/// will keep, even when the per-message budget would normally drop more.
/// Below this, conversations lose enough context that the model starts
/// hallucinating prior tool results.
const TRIM_MIN_MESSAGES: usize = 10;
impl ConversationHistory {
/// Trim messages to stay within token budget.
pub(super) fn trim_if_needed(&mut self) {
let len_before = self.messages.len();
if self.messages.len() > self.config.max_messages {
let remove_count = self.messages.len() - self.config.max_messages;
self.messages.drain(0..remove_count);
}
let mut total_tokens = self.estimate_total_tokens();
while total_tokens > self.config.max_context_tokens && self.messages.len() > 10 {
let removed_tokens = Self::estimate_message_tokens(&self.messages[0]);
self.messages.remove(0);
total_tokens -= removed_tokens;
}
// Trimming from the front can strand a user message whose
// ToolResult blocks reference a ToolUse in an already-dropped
// assistant message. The OpenAI Responses API rejects this with
// "No tool call found for function call output with call_id …".
// Drop any leading messages that still carry orphaned tool
// results so the serialized history stays self-consistent. The
// drop can move the total token count, so recompute before the
// "approaching limit" warning to avoid reporting stale numbers.
let stripped_orphan = self.drop_leading_orphaned_tool_results();
total_tokens = self.estimate_total_tokens();
// Invalidate the anchor when ANY front-of-history mutation
// happened — index shift OR in-place strip of `messages[0]`
// (the latter changes the prefix hash for every anchor
// position, since the prefix up to the anchor includes
// `messages[0]`). Pure appends leave the anchor untouched.
if self.messages.len() != len_before || stripped_orphan {
self.invalidate_cache_anchor();
}
// The warning describes our internal trim heuristic, not the
// model's API context window — those are different numbers.
// The condition below means: we tried to trim down to budget
// but hit the `TRIM_MIN_MESSAGES` floor. The model API will
// still accept the request; this just warns the user that
// auto-trim can't help further. Dedup with `warned_at_floor`
// so a long agent loop doesn't print the warning on every
// tool round-trip.
let at_floor = total_tokens > self.config.max_context_tokens
&& self.messages.len() <= TRIM_MIN_MESSAGES;
if at_floor {
if !self.warned_at_floor {
tracing::warn!(
floor = TRIM_MIN_MESSAGES,
tokens = total_tokens,
budget = self.config.max_context_tokens,
"auto-trim hit the message floor; run /compact or /clear if responses degrade"
);
self.warned_at_floor = true;
}
} else {
self.warned_at_floor = false;
}
self.maintain_cache_anchor();
}
pub(super) fn message_block_count(msg: &Message) -> usize {
match &msg.content {
crate::api::MessageContent::Text { .. } => 1,
crate::api::MessageContent::Blocks { content } => content.len(),
}
}
/// Drives the "advance the anchor?" decision in
/// `maintain_cache_anchor` against Anthropic's 20-block lookback
/// window — note this excludes the rolling message itself, so a
/// single very wide rolling message doesn't force an advance.
pub(super) fn block_distance(&self, from: usize, to: usize) -> usize {
self.messages[from..to]
.iter()
.map(Self::message_block_count)
.sum()
}
/// Pick the secondary `cache_control` ("anchor") position so that
/// even a single iteration adding more than 20 blocks still finds
/// at least one cached entry within Anthropic's lookback window.
/// The anchor stays put across turns until the rolling breakpoint
/// has drifted more than ~18 blocks past it; then it advances to
/// roughly 10 blocks behind the current rolling. Stamps only land
/// on Blocks-variant messages — Text-variant has no per-block
/// `cache_control` field, so picking one would silently waste the
/// 4th breakpoint slot.
pub(super) fn maintain_cache_anchor(&mut self) {
const KEEP_DISTANCE_BLOCKS: usize = 18;
const TARGET_OFFSET_BLOCKS: usize = 10;
let len = self.messages.len();
if len < 2 {
self.cache_anchor_message_idx = None;
return;
}
let rolling_idx = len - 1;
if let Some(idx) = self.cache_anchor_message_idx {
let still_valid = idx < rolling_idx
&& matches!(
self.messages[idx].content,
crate::api::MessageContent::Blocks { .. }
);
if !still_valid {
self.cache_anchor_message_idx = None;
}
}
if let Some(idx) = self.cache_anchor_message_idx {
if self.block_distance(idx, rolling_idx) <= KEEP_DISTANCE_BLOCKS {
return;
}
}
let mut blocks_back = 0;
for i in (0..rolling_idx).rev() {
blocks_back += Self::message_block_count(&self.messages[i]);
if blocks_back >= TARGET_OFFSET_BLOCKS
&& matches!(
self.messages[i].content,
crate::api::MessageContent::Blocks { .. }
)
{
self.cache_anchor_message_idx = Some(i);
return;
}
}
self.cache_anchor_message_idx = None;
}
pub fn cache_anchor_message_idx(&self) -> Option<usize> {
self.cache_anchor_message_idx
}
/// Drop the secondary cache-control breakpoint. Call this from any
/// mutator that changes content at or before the current anchor or
/// shifts indices into the anchored prefix; the next
/// [`Self::maintain_cache_anchor`] re-establishes the anchor from
/// the new state. Tail-only mutations (append, `last_mut`, pop the
/// rolling) leave the anchor valid and must NOT call this.
pub(super) fn invalidate_cache_anchor(&mut self) {
self.cache_anchor_message_idx = None;
}
/// Drop leading messages whose content still references tool calls
/// that have been trimmed away. Called after any operation that
/// removes messages from the front of the history. Returns `true`
/// if any blocks were stripped or any message was removed — the
/// cache anchor must be invalidated in either case because the
/// prefix bytes up to the anchor include `messages[0]`.
///
/// Preserves sibling `Text` / `Image` blocks in mixed user messages.
/// A user turn can legitimately carry `[ToolResult, Text]` — the
/// `Text` is a steer message that was folded into the tool-results
/// turn (see `response_handler::drain_steer_messages`). If trim
/// drops the preceding assistant `ToolUse`, the `ToolResult` is
/// orphaned but the `Text` isn't. Strip only the orphaned blocks;
/// remove the whole message only when nothing survives the strip.
pub(super) fn drop_leading_orphaned_tool_results(&mut self) -> bool {
let mut mutated = false;
loop {
let head_has_orphan = self
.messages
.first()
.is_some_and(|m| m.role == "user" && Self::message_has_tool_result(m));
if !head_has_orphan {
return mutated;
}
mutated = true;
if let crate::api::MessageContent::Blocks { content } = &mut self.messages[0].content {
content
.retain(|b| !matches!(b, crate::api::MessageContentBlock::ToolResult { .. }));
if !content.is_empty() {
return mutated;
}
}
self.messages.remove(0);
}
}
pub(super) fn message_has_tool_result(msg: &Message) -> bool {
matches!(
&msg.content,
crate::api::MessageContent::Blocks { content }
if content.iter().any(|b| matches!(
b,
crate::api::MessageContentBlock::ToolResult { .. }
))
)
}
/// Build a brief summary of messages about to be dropped (no LLM, just key facts).
pub(super) fn build_drop_summary(messages: &[Message]) -> String {
let mut tools_used = Vec::new();
let mut files_mentioned = Vec::new();
let mut user_topics = Vec::new();
let text_preview = |text: &str| -> Option<String> {
let preview = if text.len() > 100 {
format!("{}...", &text[..truncate_at_char_boundary(text, 100)])
} else {
text.to_string()
};
if preview.trim().is_empty() {
None
} else {
Some(preview)
}
};
for msg in messages {
let is_user = msg.role == "user";
match &msg.content {
crate::api::MessageContent::Blocks { content } => {
for block in content {
match block {
crate::api::MessageContentBlock::ToolUse { name, input, .. } => {
if !tools_used.contains(name) {
tools_used.push(name.clone());
}
if let Some(path) = input.get("path").and_then(|v| v.as_str()) {
let p = path.to_string();
if !files_mentioned.contains(&p) {
files_mentioned.push(p);
}
}
}
crate::api::MessageContentBlock::Text { text, .. } if is_user => {
if let Some(preview) = text_preview(text) {
user_topics.push(preview);
}
}
_ => {}
}
}
}
crate::api::MessageContent::Text { content } if is_user => {
if let Some(preview) = text_preview(content) {
user_topics.push(preview);
}
}
_ => {}
}
}
let mut parts = Vec::new();
if !user_topics.is_empty() {
let topics: Vec<_> = user_topics.into_iter().take(5).collect();
parts.push(format!("User requests: {}", topics.join(" | ")));
}
if !tools_used.is_empty() {
parts.push(format!("Tools used: {}", tools_used.join(", ")));
}
if !files_mentioned.is_empty() {
let files: Vec<_> = files_mentioned.into_iter().take(20).collect();
parts.push(format!("Files: {}", files.join(", ")));
}
parts.join("\n")
}
/// Fallback trim used when compaction fails.
/// Builds a mechanical summary of dropped messages before trimming.
pub fn fallback_trim(&mut self) {
let msg_count_before = self.messages.len();
if msg_count_before <= 10 {
self.trim_if_needed();
return;
}
// Simulate trim_if_needed to find which messages will be dropped
let max_msg_drop = self.messages.len().saturating_sub(self.config.max_messages);
let mut token_drop = 0;
let mut simulated_tokens = self.estimate_total_tokens();
for msg in self.messages.iter().take(max_msg_drop) {
simulated_tokens -= Self::estimate_message_tokens(msg);
}
let remaining = self.messages.len() - max_msg_drop;
for i in 0..remaining.saturating_sub(10) {
if simulated_tokens <= self.config.max_context_tokens {
break;
}
simulated_tokens -= Self::estimate_message_tokens(&self.messages[max_msg_drop + i]);
token_drop += 1;
}
let total_drop = max_msg_drop + token_drop;
let summary = if total_drop >= 5 {
Self::build_drop_summary(&self.messages[..total_drop])
} else {
String::new()
};
self.trim_if_needed();
if !summary.is_empty() {
let dropped = msg_count_before - self.messages.len();
let summary_msg = Message::user(format!(
"[Context trimmed — {} earlier messages dropped]\n\n{}",
dropped, summary
));
self.messages.insert(0, summary_msg);
}
}
}