6 files changed, 365 insertions, 1 deletions
diff --git a/internal/cli/run.go b/internal/cli/run.go
index 2da7b79..2d7c3d7 100644
--- a/internal/cli/run.go
+++ b/internal/cli/run.go
@@ -100,6 +100,9 @@ func runTasks(file string, parallel int, dryRun bool) error {
 		LLM:              localClient,
 		GeminiBinaryPath: cfg.GeminiBinaryPath,
 	}
+	if localClient != nil {
+		pool.LLM = localClient
+	}
 
 	// Handle graceful shutdown.
 	ctx, cancel := context.WithCancel(context.Background())
diff --git a/internal/cli/serve.go b/internal/cli/serve.go
index 2263d01..5101b81 100644
--- a/internal/cli/serve.go
+++ b/internal/cli/serve.go
@@ -88,6 +88,9 @@ func serve(addr string) error {
 		LLM:              localClient,
 		GeminiBinaryPath: cfg.GeminiBinaryPath,
 	}
+	if localClient != nil {
+		pool.LLM = localClient
+	}
 	pool.RecoverStaleRunning(context.Background())
 	pool.RecoverStaleQueued(context.Background())
 	pool.RecoverStaleBlocked()
diff --git a/internal/executor/executor.go b/internal/executor/executor.go
index f5aabe1..4501a3c 100644
--- a/internal/executor/executor.go
+++ b/internal/executor/executor.go
@@ -10,6 +10,7 @@ import (
 	"sync"
 	"time"
 
+	"github.com/thepeterstone/claudomator/internal/llm"
 	"github.com/thepeterstone/claudomator/internal/retry"
 	"github.com/thepeterstone/claudomator/internal/storage"
 	"github.com/thepeterstone/claudomator/internal/task"
@@ -70,6 +71,9 @@ type Pool struct {
 	doneCh         chan struct{}  // signals when a worker slot is freed
 	Questions      *QuestionRegistry
 	Classifier     *Classifier
+	// LLM, when non-nil, enables LLM-synthesized summaries for executions
+	// whose stdout did not include a "## Summary" heading.
+	LLM *llm.Client
 }
 
 // Result is emitted when a task execution completes.
@@ -349,6 +353,9 @@ func (p *Pool) handleRunResult(ctx context.Context, t *task.Task, exec *storage.
 	if summary == "" && exec.StdoutPath != "" {
 		summary = extractSummary(exec.StdoutPath)
 	}
+	if summary == "" && p.LLM != nil && exec.StdoutPath != "" {
+		summary = synthesizeSummary(ctx, p.LLM, exec.StdoutPath)
+	}
 	if summary != "" {
 		if summaryErr := p.store.UpdateTaskSummary(t.ID, summary); summaryErr != nil {
 			p.logger.Error("failed to update task summary", "taskID", t.ID, "error", summaryErr)
diff --git a/internal/executor/executor_test.go b/internal/executor/executor_test.go
index 878a32d..b1173cb 100644
--- a/internal/executor/executor_test.go
+++ b/internal/executor/executor_test.go
@@ -980,6 +980,7 @@ type minimalMockStore struct {
 	executions      map[string]*storage.Execution
 	stateUpdates    []struct{ id string; state task.State }
 	questionUpdates []string
+	summaryUpdates  []struct{ taskID, summary string }
 	changestatCalls []struct {
 		execID string
 		stats  *task.Changestats
@@ -1035,7 +1036,21 @@ func (m *minimalMockStore) UpdateTaskQuestion(taskID, questionJSON string) error
 	m.mu.Unlock()
 	return nil
 }
-func (m *minimalMockStore) UpdateTaskSummary(taskID, summary string) error        { return nil }
+func (m *minimalMockStore) UpdateTaskSummary(taskID, summary string) error {
+	m.mu.Lock()
+	m.summaryUpdates = append(m.summaryUpdates, struct{ taskID, summary string }{taskID, summary})
+	m.mu.Unlock()
+	return nil
+}
+func (m *minimalMockStore) lastSummaryUpdate() (string, string, bool) {
+	m.mu.Lock()
+	defer m.mu.Unlock()
+	if len(m.summaryUpdates) == 0 {
+		return "", "", false
+	}
+	last := m.summaryUpdates[len(m.summaryUpdates)-1]
+	return last.taskID, last.summary, true
+}
 func (m *minimalMockStore) AppendTaskInteraction(taskID string, _ task.Interaction) error {
 	return nil
 }
diff --git a/internal/executor/summary.go b/internal/executor/summary.go
index a942de0..bcf5cfd 100644
--- a/internal/executor/summary.go
+++ b/internal/executor/summary.go
@@ -2,11 +2,26 @@ package executor
 
 import (
 	"bufio"
+	"context"
 	"encoding/json"
+	"io"
 	"os"
 	"strings"
+	"time"
+
+	"github.com/thepeterstone/claudomator/internal/llm"
 )
 
+// synthesizeSummaryMaxBytes caps how much of the stdout log we send to the
+// LLM. Larger values cost more tokens with diminishing returns for a 2-4
+// sentence summary.
+const synthesizeSummaryMaxBytes = 16 * 1024
+
+// synthesizeSummaryTimeout caps the LLM call so a slow local model can't
+// stall executor finalization. On timeout, we return "" (the existing
+// no-summary path takes over).
+const synthesizeSummaryTimeout = 6 * time.Second
+
 // extractSummary reads a stream-json stdout log and returns the text following
 // the last "## Summary" heading found in any assistant text block.
 // Returns empty string if the file cannot be read or no summary is found.
@@ -28,6 +43,86 @@ func extractSummary(stdoutPath string) string {
 	return last
 }
 
+// synthesizeSummary asks the LLM to summarize the assistant text content in
+// stdoutPath when no "## Summary" heading was present. Returns "" on any
+// error, an empty file, or an empty model response — preserving the
+// existing "no summary" behavior so the new path is purely additive.
+func synthesizeSummary(parent context.Context, c *llm.Client, stdoutPath string) string {
+	if c == nil || stdoutPath == "" {
+		return ""
+	}
+	text := readAssistantTextTail(stdoutPath, synthesizeSummaryMaxBytes)
+	if strings.TrimSpace(text) == "" {
+		return ""
+	}
+
+	cctx, cancel := context.WithTimeout(parent, synthesizeSummaryTimeout)
+	defer cancel()
+	resp, err := c.Chat(cctx, llm.ChatRequest{
+		Messages: []llm.Message{
+			{Role: "system", Content: "You summarize what an automated coding agent did. Reply with 2-4 sentences of plain prose. No bullets, no headings, no preamble."},
+			{Role: "user", Content: "Here is the agent's output. Summarize what it accomplished:\n\n" + text},
+		},
+	})
+	if err != nil {
+		return ""
+	}
+	return strings.TrimSpace(resp.Content)
+}
+
+// readAssistantTextTail returns the concatenated `text` blocks from assistant
+// stream-json events in the last maxBytes of the file. Non-assistant events
+// (system, result, tool_use, etc.) are skipped so the LLM sees just what the
+// agent said. Returns "" on any error.
+func readAssistantTextTail(stdoutPath string, maxBytes int64) string {
+	f, err := os.Open(stdoutPath)
+	if err != nil {
+		return ""
+	}
+	defer f.Close()
+
+	stat, err := f.Stat()
+	if err != nil {
+		return ""
+	}
+	size := stat.Size()
+	if size > maxBytes {
+		if _, err := f.Seek(size-maxBytes, io.SeekStart); err != nil {
+			return ""
+		}
+	}
+
+	var sb strings.Builder
+	scanner := bufio.NewScanner(f)
+	scanner.Buffer(make([]byte, 1024*1024), 1024*1024)
+	first := size > maxBytes // if we seeked, drop the first (likely partial) line
+	for scanner.Scan() {
+		if first {
+			first = false
+			continue
+		}
+		var event struct {
+			Type    string `json:"type"`
+			Message struct {
+				Content []struct {
+					Type string `json:"type"`
+					Text string `json:"text"`
+				} `json:"content"`
+			} `json:"message"`
+		}
+		if err := json.Unmarshal(scanner.Bytes(), &event); err != nil || event.Type != "assistant" {
+			continue
+		}
+		for _, block := range event.Message.Content {
+			if block.Type == "text" && block.Text != "" {
+				sb.WriteString(block.Text)
+				sb.WriteString("\n")
+			}
+		}
+	}
+	return sb.String()
+}
+
 // summaryFromLine parses a single stream-json line and returns the text after
 // "## Summary" if the line is an assistant text block containing that heading.
 func summaryFromLine(line []byte) string {
diff --git a/internal/executor/summary_synth_test.go b/internal/executor/summary_synth_test.go
new file mode 100644
index 0000000..7ad396d
--- /dev/null
+++ b/internal/executor/summary_synth_test.go
@@ -0,0 +1,241 @@
+package executor
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"net/http"
+	"net/http/httptest"
+	"os"
+	"path/filepath"
+	"strings"
+	"sync/atomic"
+	"testing"
+
+	"github.com/thepeterstone/claudomator/internal/llm"
+	"github.com/thepeterstone/claudomator/internal/storage"
+)
+
+func writeStreamLog(t *testing.T, lines []string) string {
+	t.Helper()
+	dir := t.TempDir()
+	path := filepath.Join(dir, "stdout.log")
+	var sb strings.Builder
+	for _, l := range lines {
+		sb.WriteString(l)
+		sb.WriteString("\n")
+	}
+	if err := os.WriteFile(path, []byte(sb.String()), 0600); err != nil {
+		t.Fatal(err)
+	}
+	return path
+}
+
+func TestSynthesizeSummary_NilClient(t *testing.T) {
+	got := synthesizeSummary(context.Background(), nil, "/some/path")
+	if got != "" {
+		t.Errorf("nil client: want empty, got %q", got)
+	}
+}
+
+func TestSynthesizeSummary_EmptyPath(t *testing.T) {
+	c := &llm.Client{Endpoint: "http://unused", Model: "x"}
+	got := synthesizeSummary(context.Background(), c, "")
+	if got != "" {
+		t.Errorf("empty path: want empty, got %q", got)
+	}
+}
+
+func TestSynthesizeSummary_MissingFile(t *testing.T) {
+	c := &llm.Client{Endpoint: "http://unused", Model: "x"}
+	got := synthesizeSummary(context.Background(), c, "/nonexistent/file.log")
+	if got != "" {
+		t.Errorf("missing file: want empty, got %q", got)
+	}
+}
+
+func TestSynthesizeSummary_EmptyAssistantContent(t *testing.T) {
+	// Log contains only system/result events — no assistant text. The function
+	// should short-circuit without calling the LLM.
+	path := writeStreamLog(t, []string{
+		`{"type":"system","subtype":"init"}`,
+		`{"type":"result","subtype":"success","total_cost_usd":0}`,
+	})
+
+	var calls int32
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		atomic.AddInt32(&calls, 1)
+		w.Header().Set("Content-Type", "application/json")
+		fmt.Fprintln(w, `{"choices":[{"message":{"content":"should not be returned"},"finish_reason":"stop"}],"usage":{}}`)
+	}))
+	defer srv.Close()
+	c := &llm.Client{Endpoint: srv.URL + "/v1", Model: "x"}
+
+	got := synthesizeSummary(context.Background(), c, path)
+	if got != "" {
+		t.Errorf("empty content: want empty, got %q", got)
+	}
+	if atomic.LoadInt32(&calls) != 0 {
+		t.Errorf("LLM should not be called for empty assistant content")
+	}
+}
+
+func TestSynthesizeSummary_LLMSuccess(t *testing.T) {
+	path := writeStreamLog(t, []string{
+		`{"type":"assistant","message":{"content":[{"type":"text","text":"Ran the tests."}]}}`,
+		`{"type":"assistant","message":{"content":[{"type":"text","text":"Fixed the import."}]}}`,
+		`{"type":"result","subtype":"success"}`,
+	})
+
+	var capturedUser string
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		var body struct {
+			Messages []struct {
+				Role, Content string
+			} `json:"messages"`
+		}
+		json.NewDecoder(r.Body).Decode(&body)
+		for _, m := range body.Messages {
+			if m.Role == "user" {
+				capturedUser = m.Content
+			}
+		}
+		w.Header().Set("Content-Type", "application/json")
+		fmt.Fprintln(w, `{"choices":[{"message":{"content":"  Agent ran tests and fixed an import.  "},"finish_reason":"stop"}],"usage":{}}`)
+	}))
+	defer srv.Close()
+	c := &llm.Client{Endpoint: srv.URL + "/v1", Model: "x"}
+
+	got := synthesizeSummary(context.Background(), c, path)
+	if got != "Agent ran tests and fixed an import." {
+		t.Errorf("summary: got %q", got)
+	}
+	if !strings.Contains(capturedUser, "Ran the tests.") {
+		t.Errorf("user prompt missing first assistant text; got: %s", capturedUser)
+	}
+	if !strings.Contains(capturedUser, "Fixed the import.") {
+		t.Errorf("user prompt missing second assistant text; got: %s", capturedUser)
+	}
+}
+
+// TestPool_HandleRunResult_LLMSummaryFallback verifies the Pool falls back to
+// LLM-synthesized summary when extractSummary returns empty.
+func TestPool_HandleRunResult_LLMSummaryFallback(t *testing.T) {
+	// stdout has assistant text but no "## Summary" heading.
+	stdoutPath := writeStreamLog(t, []string{
+		`{"type":"assistant","message":{"content":[{"type":"text","text":"Did the work without writing a summary section."}]}}`,
+	})
+
+	llmSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		fmt.Fprintln(w, `{"choices":[{"message":{"content":"Synthesized summary."},"finish_reason":"stop"}],"usage":{}}`)
+	}))
+	defer llmSrv.Close()
+
+	store := newMinimalMockStore()
+	pool := newPoolWithMockStore(store)
+	pool.LLM = &llm.Client{Endpoint: llmSrv.URL + "/v1", Model: "x"}
+
+	tk := makeTask("synth-summary")
+	store.tasks[tk.ID] = tk
+	exec := &storage.Execution{ID: "e-synth", TaskID: tk.ID, Status: "RUNNING", StdoutPath: stdoutPath}
+
+	pool.handleRunResult(context.Background(), tk, exec, nil, "claude")
+
+	id, summary, ok := store.lastSummaryUpdate()
+	if !ok {
+		t.Fatalf("expected UpdateTaskSummary to be called")
+	}
+	if id != tk.ID {
+		t.Errorf("summary recorded for wrong task: %q", id)
+	}
+	if summary != "Synthesized summary." {
+		t.Errorf("summary: got %q", summary)
+	}
+
+	// Drain the result channel so the test exits cleanly.
+	<-pool.resultCh
+}
+
+// TestPool_HandleRunResult_ExtractSummaryWins verifies the LLM is NOT called
+// when the agent already wrote a "## Summary" section.
+func TestPool_HandleRunResult_ExtractSummaryWins(t *testing.T) {
+	stdoutPath := writeStreamLog(t, []string{
+		`{"type":"assistant","message":{"content":[{"type":"text","text":"## Summary\nAgent wrote its own summary."}]}}`,
+	})
+
+	var llmCalls int32
+	llmSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		atomic.AddInt32(&llmCalls, 1)
+		w.Header().Set("Content-Type", "application/json")
+		fmt.Fprintln(w, `{"choices":[{"message":{"content":"should not be used"},"finish_reason":"stop"}],"usage":{}}`)
+	}))
+	defer llmSrv.Close()
+
+	store := newMinimalMockStore()
+	pool := newPoolWithMockStore(store)
+	pool.LLM = &llm.Client{Endpoint: llmSrv.URL + "/v1", Model: "x"}
+
+	tk := makeTask("agent-summary")
+	store.tasks[tk.ID] = tk
+	exec := &storage.Execution{ID: "e-agent", TaskID: tk.ID, Status: "RUNNING", StdoutPath: stdoutPath}
+
+	pool.handleRunResult(context.Background(), tk, exec, nil, "claude")
+
+	if got := atomic.LoadInt32(&llmCalls); got != 0 {
+		t.Errorf("LLM should not be called when ## Summary is present; got %d calls", got)
+	}
+	_, summary, ok := store.lastSummaryUpdate()
+	if !ok {
+		t.Fatalf("expected UpdateTaskSummary")
+	}
+	if summary != "Agent wrote its own summary." {
+		t.Errorf("summary: got %q (want extractSummary output)", summary)
+	}
+	<-pool.resultCh
+}
+
+func TestSynthesizeSummary_LLMFailure_ReturnsEmpty(t *testing.T) {
+	path := writeStreamLog(t, []string{
+		`{"type":"assistant","message":{"content":[{"type":"text","text":"Did something."}]}}`,
+	})
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		http.Error(w, "boom", http.StatusInternalServerError)
+	}))
+	defer srv.Close()
+	c := &llm.Client{Endpoint: srv.URL + "/v1", Model: "x"}
+
+	got := synthesizeSummary(context.Background(), c, path)
+	if got != "" {
+		t.Errorf("LLM failure: want empty, got %q", got)
+	}
+}
+
+// TestReadAssistantTextTail_TailingLargeFile verifies the seek-to-tail
+// behavior drops early content but keeps later assistant text.
+func TestReadAssistantTextTail_TailingLargeFile(t *testing.T) {
+	dir := t.TempDir()
+	path := filepath.Join(dir, "stdout.log")
+	f, err := os.Create(path)
+	if err != nil {
+		t.Fatal(err)
+	}
+	// Write a ton of garbage assistant lines, then a final marker.
+	for i := 0; i < 500; i++ {
+		fmt.Fprintf(f, `{"type":"assistant","message":{"content":[{"type":"text","text":"filler line that should be in the early part of a large file %04d"}]}}`+"\n", i)
+	}
+	fmt.Fprintln(f, `{"type":"assistant","message":{"content":[{"type":"text","text":"FINAL_MARKER_LINE"}]}}`)
+	f.Close()
+
+	got := readAssistantTextTail(path, 4*1024) // 4 KB cap
+	if !strings.Contains(got, "FINAL_MARKER_LINE") {
+		t.Errorf("tail should contain final line; got: %s", got)
+	}
+	if strings.Contains(got, "filler line that should be in the early part of a large file 0000") {
+		end := 200
+		if len(got) < end {
+			end = len(got)
+		}
+		t.Errorf("tail should NOT contain very-early line; got first 200 chars: %s", got[:end])
+	}
+}