From fc77c3900ef80ff0e2934c03ca37dfc309a6e7b9 Mon Sep 17 00:00:00 2001
From: t <t@tjp.lol>
Date: Thu, 18 Jun 2026 11:47:07 -0600
Subject: fix compaction in the presence of consecutive user-role messages

---
 libpanto/src/compaction.zig | 85 +++++++++++++++++++++++++++++++++++++++++----
 1 file changed, 79 insertions(+), 6 deletions(-)

(limited to 'libpanto/src/compaction.zig')

diff --git a/libpanto/src/compaction.zig b/libpanto/src/compaction.zig
index 3a1c012..dfa3242 100644
--- a/libpanto/src/compaction.zig
+++ b/libpanto/src/compaction.zig
@@ -247,7 +247,7 @@ pub fn computeSplit(
     while (i < messages.len) : (i += 1) {
         const msg = messages[i];
         if (msg.role == .system) continue;
-        if (isTurnStart(msg)) {
+        if (isTurnStart(messages, i)) {
             if (n_turns < turn_starts_buf.len) {
                 turn_starts_buf[n_turns] = i;
             }
@@ -302,18 +302,52 @@ pub fn computeSplit(
     return .{ .prefix_end = first_turn_msg, .kept_turns = kept_turns };
 }
 
-/// A user message starts a new turn unless it carries any tool-result
-/// block (in which case it's a continuation of the assistant's tool round
-/// within the current turn). System and assistant messages never start a
-/// turn.
-fn isTurnStart(msg: Message) bool {
+/// Whether the message at `index` begins a new turn.
+///
+/// A turn starts at a user message that is both:
+///   (a) not a tool-result message — a user message carrying any tool-result
+///       block continues the assistant's current tool round, and
+///   (b) the *first* user message after a non-user message (or the start of
+///       the conversation).
+///
+/// Condition (b) collapses a run of consecutive plain user messages into a
+/// single turn: only the first is a boundary. Without it, each bare user
+/// message would be its own turn, and the ones with no trailing assistant
+/// would fall to the per-message word-count fallback and be counted a second
+/// time on top of the turn's cumulative-usage delta (which already includes
+/// them). System and assistant messages never start a turn; preceding system
+/// messages are transparent for the "after a non-user message" test.
+fn isTurnStart(messages: []const Message, index: usize) bool {
+    const msg = messages[index];
     if (msg.role != .user) return false;
     for (msg.content.items) |block| {
         if (block == .ToolResult) return false;
     }
+    // First user message after a non-user message, or the start of the
+    // active window. Structural frame messages are transparent here: leading
+    // system prompts and the compaction-summary anchor (a synthetic `.user`
+    // message) are not conversational user turns, so a real user message
+    // following one still opens a turn.
+    var j = index;
+    while (j > 0) {
+        j -= 1;
+        if (isStructuralFrame(messages[j])) continue;
+        return messages[j].role != .user;
+    }
     return true;
 }
 
+/// Whether a message is part of the structural frame rather than a
+/// conversational turn: a system message, or the synthetic `.user` message
+/// carrying a compaction summary that anchors an active window.
+fn isStructuralFrame(msg: Message) bool {
+    if (msg.role == .system) return true;
+    for (msg.content.items) |block| {
+        if (block == .CompactionSummary) return true;
+    }
+    return false;
+}
+
 // =============================================================================
 // Transcript serialization
 // =============================================================================
@@ -592,6 +626,45 @@ test "computeSplit - tool-result user messages attach to the current turn" {
     try testing.expectEqual(@as(usize, 1), split.kept_turns);
 }
 
+test "computeSplit - consecutive user messages collapse into a single turn" {
+    const a = testing.allocator;
+    // Three plain user messages in a row open ONE turn, not three: only the
+    // first follows a non-user message; the others are continuations.
+    var msgs = [_]Message{
+        try userMsg(a, "a"),
+        try userMsg(a, "b"),
+        try userMsg(a, "c"),
+        try asstMsg(a, "a1"),
+        try userMsg(a, "q2"),
+        try asstMsg(a, "a2"),
+    };
+    defer freeMsgs(a, &msgs);
+
+    // Whole conversation fits: nothing is summarized and the leading run of
+    // user messages counts as a single turn, so kept_turns == 2 (not 4).
+    {
+        const split = computeSplit(&msgs, null, 1_000_000);
+        try testing.expectEqual(@as(usize, 0), split.prefix_end);
+        try testing.expectEqual(@as(usize, 2), split.kept_turns);
+    }
+
+    // With usage, the first turn's cumulative delta already accounts for
+    // a+b+c+a1, so the per-message fallback must not charge a/b a second
+    // time. Turn deltas: turn 1 = cumAt(a1) - 0 = 400; turn 2 = cumAt(a2) -
+    // cumAt(a1) = 600 - 400 = 200. Budget 250 keeps only turn 2 and
+    // summarizes the entire collapsed first turn, so the kept suffix begins
+    // at q2 (index 4).
+    {
+        const usages = [_]?Usage{
+            .{ .input = 0 }, .{ .input = 0 }, .{ .input = 0 }, .{ .input = 300, .output = 100 },
+            .{ .input = 0 }, .{ .input = 500, .output = 100 },
+        };
+        const split = computeSplit(&msgs, &usages, 250);
+        try testing.expectEqual(@as(usize, 4), split.prefix_end);
+        try testing.expectEqual(@as(usize, 1), split.kept_turns);
+    }
+}
+
 test "computeSplit - active window starts after an existing compaction summary" {
     const a = testing.allocator;
     var msgs = [_]Message{
-- 
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