feat(run): durable checkpoint + resume (wire Ports.Checkpointer)

The kernel defined run.Ports.Checkpointer + the checkpoint battery but never
drove them (the documented "P2 follow-up"). This wires durable recovery into
the run loop so a run interrupted by shutdown can resume on the next boot
instead of being lost — the executus-side half of mort's durable-agent-recovery
parity (mort #1355).

Kernel (run/):
- Ports.Checkpointer is now a CheckpointerFactory (Begin per run → a per-run
  Checkpointer, or nil for a non-durable run). The single per-instance
  Checkpointer couldn't distinguish runs; a factory mints one per run, matching
  mort's agentexec.CheckpointerFactory.
- RunInfo gains GuildID + ModelTier (so the factory can build resume meta);
  RunCheckpointState gains CompletedPhases + ActivePhase (+ PhaseOutput).
- run/checkpoint.go: ResumeState + WithResumeState / WithExistingCheckpointer
  context carriers, classifyCheckpointOutcome (success→Complete, shutdown→leave
  for boot recovery, else→Fail using run.ErrShutdown), and finalizeCheckpoint.
- run/executor.go: resolve the per-run checkpointer (existing-from-ctx on a
  recovery re-run, else factory.Begin); single-loop wraps the step observer to
  accumulate the transcript + Save each step (host throttles), and a recovered
  run seeds the saved transcript via WithHistory and continues with no new
  input; finalize on exit.
- run/phases.go: phase-boundary checkpointing — record completed phases after
  each phase; a resumed run skips already-completed phases (the interrupted
  phase re-runs from its start — boundary-granular, documented; only the
  single-loop path resumes mid-loop).

Battery (checkpoint/): NewFactory wires the battery into the factory port
(per-run handle, meta derived from RunInfo); RunCheckpoint + handle.Save carry
the phase fields.

Tests (run/checkpoint_test.go): the finalize decision matrix; single-loop
Save+Complete; terminal-error Fail; resume seeds history; phase-boundary Saves
completed phases; resume skips completed phases. Full ./... green.

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

checkpoint/checkpoint.go

@@ -4,9 +4,9 @@
 // run.Ports.Checkpointer.
 //
 // Mort backs CheckpointStore with its durable-job table; Memory() is the
-// zero-dependency default; contrib/store can add a SQLite one. NOTE: the
-// executor's call into run.Ports.Checkpointer is a P2 follow-up — this battery
-// provides the seam + impls ahead of that wiring.
+// zero-dependency default; contrib/store can add a SQLite one. The executor calls
+// run.Ports.Checkpointer (a CheckpointerFactory) during the run loop; NewFactory
+// wires this battery into that seam.
 package checkpoint
 
 import (
@@ -14,6 +14,8 @@ import (
 	"time"
 
 	"gitea.stevedudenhoeffer.com/steve/majordomo/llm"
+
+	"gitea.stevedudenhoeffer.com/steve/executus/run"
 )
 
 // RunCheckpointMeta is the run attribution needed to resume a run from scratch
@@ -33,8 +35,9 @@ type RunCheckpointMeta struct {
 // RunCheckpoint is one persisted snapshot of a run's resumable progress.
 type RunCheckpoint struct {
 	Meta            RunCheckpointMeta
-	Messages    []llm.Message // conversation so far
+	Messages        []llm.Message     // conversation so far (single-loop or active phase)
 	Iteration       int               // completed agent-loop iterations
+	CompletedPhases []run.PhaseOutput // finished phases, in order (multi-phase agents)
 	ActivePhase     string            // current phase name (multi-phase agents); "" otherwise
 	UpdatedAt       time.Time
 }

checkpoint/handle.go

@@ -57,6 +57,8 @@ func (h *handle) Save(ctx context.Context, st run.RunCheckpointState) error {
 		Meta:            h.meta,
 		Messages:        st.Messages,
 		Iteration:       st.Iteration,
+		CompletedPhases: st.CompletedPhases,
+		ActivePhase:     st.ActivePhase,
 		UpdatedAt:       now,
 	}); err != nil {
 		return err
@@ -81,3 +83,41 @@ var _ run.Checkpointer = noop{}
 func (noop) Save(context.Context, run.RunCheckpointState) error { return nil }
 func (noop) Complete(context.Context) error                     { return nil }
 func (noop) Fail(context.Context, error) error                  { return nil }
+
+// factory is a run.CheckpointerFactory that mints a per-run handle over store,
+// deriving the per-run meta from the kernel's RunInfo. It is the battery's glue
+// for the Ports.Checkpointer (factory) seam: every run becomes durable (the
+// store persists snapshots; a host wanting lazy/short-run skipping uses its own
+// factory, as mort does over its durable-job table).
+type factory struct {
+	store    CheckpointStore
+	throttle time.Duration
+	now      func() time.Time
+}
+
+var _ run.CheckpointerFactory = (*factory)(nil)
+
+// NewFactory returns a run.CheckpointerFactory backed by store: each run gets a
+// per-run Checkpointer (throttled to at most once per throttle). A nil store
+// yields factory.Begin returning a no-op Checkpointer.
+func NewFactory(store CheckpointStore, throttle time.Duration) run.CheckpointerFactory {
+	return &factory{store: store, throttle: throttle}
+}
+
+// Begin mints the per-run Checkpointer. The prompt is read from
+// info.Inputs["prompt"] when present so a recovered run can re-dispatch.
+func (f *factory) Begin(_ context.Context, info run.RunInfo) (run.Checkpointer, error) {
+	prompt, _ := info.Inputs["prompt"].(string)
+	meta := RunCheckpointMeta{
+		RunID:       info.RunID,
+		AgentID:     info.SubjectID,
+		AgentName:   info.Name,
+		CallerID:    info.CallerID,
+		ChannelID:   info.ChannelID,
+		GuildID:     info.GuildID,
+		Prompt:      prompt,
+		ModelTier:   info.ModelTier,
+		ParentRunID: info.ParentRunID,
+	}
+	return New(f.store, meta, f.throttle, f.now), nil
+}

run/checkpoint.go

@@ -0,0 +1,94 @@
+package run
+
+import (
+	"context"
+	"errors"
+
+	"gitea.stevedudenhoeffer.com/steve/majordomo/llm"
+)
+
+// Durable-recovery plumbing for the executor. The Checkpointer port (set via
+// Ports.Checkpointer, a CheckpointerFactory) persists a run's resumable progress
+// during the loop; on boot a host re-dispatches an interrupted run through the
+// executor with a ResumeState (the saved transcript / completed phases) so it
+// CONTINUES rather than restarting, reusing the SAME durable record via an
+// existing Checkpointer. Both are carried into Run via the context (mirrors
+// mort's agentexec.WithResumeState / WithExistingCheckpointer).
+
+// ResumeState carries a recovered run's prior progress into Run so the run
+// continues instead of restarting. The host's recovery path sets it via
+// WithResumeState; the executor reads it (single-loop seeds the saved transcript
+// as history; multi-phase skips completed phases and seeds the active phase).
+type ResumeState struct {
+	History         []llm.Message // single-loop transcript OR active-phase transcript
+	CompletedPhases []PhaseOutput // multi-phase: outputs of finished phases, in order
+	ActivePhase     string        // multi-phase: the phase that was in flight
+}
+
+type resumeStateKey struct{}
+
+// WithResumeState carries a recovered run's prior progress into Run.
+func WithResumeState(ctx context.Context, rs *ResumeState) context.Context {
+	return context.WithValue(ctx, resumeStateKey{}, rs)
+}
+
+func resumeStateFromContext(ctx context.Context) *ResumeState {
+	rs, _ := ctx.Value(resumeStateKey{}).(*ResumeState)
+	return rs
+}
+
+type existingCheckpointerKey struct{}
+
+// WithExistingCheckpointer carries a pre-existing Checkpointer into Run so a
+// recovery re-run reuses the SAME durable record (the executor uses it instead of
+// calling Ports.Checkpointer.Begin).
+func WithExistingCheckpointer(ctx context.Context, cp Checkpointer) context.Context {
+	return context.WithValue(ctx, existingCheckpointerKey{}, cp)
+}
+
+func existingCheckpointerFromContext(ctx context.Context) Checkpointer {
+	cp, _ := ctx.Value(existingCheckpointerKey{}).(Checkpointer)
+	return cp
+}
+
+// checkpointOutcome is the finalize decision for a durable run.
+type checkpointOutcome int
+
+const (
+	checkpointComplete checkpointOutcome = iota
+	checkpointLeaveRunning
+	checkpointFail
+)
+
+// classifyCheckpointOutcome maps (run error, cancellation cause) to the durable
+// finalize action: success clears the checkpoint (Complete); a shutdown-caused
+// cancellation leaves the record so boot recovery picks it up (neither
+// Complete nor Fail); anything else (model error, tool loop, the run's own
+// deadline, a critic kill, a caller cancel) is terminal (Fail). Mirrors mort's
+// agentexec.classifyCheckpointOutcome.
+func classifyCheckpointOutcome(runErr, cause error) checkpointOutcome {
+	switch {
+	case runErr == nil:
+		return checkpointComplete
+	case errors.Is(cause, ErrShutdown):
+		return checkpointLeaveRunning
+	default:
+		return checkpointFail
+	}
+}
+
+// finalizeCheckpoint applies the outcome to the per-run checkpointer (nil-safe).
+// Runs on a detached context so a cancelled run still records its terminal state.
+func finalizeCheckpoint(ctx context.Context, cp Checkpointer, runErr error, cause error) {
+	if cp == nil {
+		return
+	}
+	switch classifyCheckpointOutcome(runErr, cause) {
+	case checkpointComplete:
+		_ = cp.Complete(detach(ctx))
+	case checkpointFail:
+		_ = cp.Fail(detach(ctx), runErr)
+	case checkpointLeaveRunning:
+		// Interrupted by shutdown: leave the record for boot recovery.
+	}
+}

run/checkpoint_test.go

@@ -0,0 +1,200 @@
+package run
+
+import (
+	"context"
+	"errors"
+	"testing"
+
+	"gitea.stevedudenhoeffer.com/steve/majordomo/llm"
+	"gitea.stevedudenhoeffer.com/steve/majordomo/provider/fake"
+
+	"gitea.stevedudenhoeffer.com/steve/executus/tool"
+)
+
+// fakeCheckpointer records every Save state + whether Complete/Fail fired.
+type fakeCheckpointer struct {
+	saves     []RunCheckpointState
+	completed bool
+	failed    bool
+	failErr   error
+}
+
+func (c *fakeCheckpointer) Save(_ context.Context, st RunCheckpointState) error {
+	c.saves = append(c.saves, st)
+	return nil
+}
+func (c *fakeCheckpointer) Complete(context.Context) error { c.completed = true; return nil }
+func (c *fakeCheckpointer) Fail(_ context.Context, err error) error {
+	c.failed = true
+	c.failErr = err
+	return nil
+}
+
+// fakeCheckpointFactory hands out one fakeCheckpointer and records the RunInfo.
+type fakeCheckpointFactory struct {
+	cp   *fakeCheckpointer
+	info RunInfo
+}
+
+func (f *fakeCheckpointFactory) Begin(_ context.Context, info RunInfo) (Checkpointer, error) {
+	f.info = info
+	return f.cp, nil
+}
+
+// TestClassifyCheckpointOutcome covers the finalize decision matrix.
+func TestClassifyCheckpointOutcome(t *testing.T) {
+	cases := []struct {
+		name  string
+		err   error
+		cause error
+		want  checkpointOutcome
+	}{
+		{"success", nil, nil, checkpointComplete},
+		{"shutdown", context.Canceled, ErrShutdown, checkpointLeaveRunning},
+		{"critic-kill", context.Canceled, ErrCriticKill, checkpointFail},
+		{"deadline", context.DeadlineExceeded, context.DeadlineExceeded, checkpointFail},
+		{"model-error", errors.New("boom"), nil, checkpointFail},
+		{"caller-cancel", context.Canceled, context.Canceled, checkpointFail},
+	}
+	for _, tc := range cases {
+		if got := classifyCheckpointOutcome(tc.err, tc.cause); got != tc.want {
+			t.Errorf("%s: classifyCheckpointOutcome = %v, want %v", tc.name, got, tc.want)
+		}
+	}
+}
+
+// TestCheckpoint_SingleLoopSaveAndComplete: a durable single-loop run gets a
+// per-run checkpointer (Begin), Saves its transcript each step, and Completes on
+// success (clearing the checkpoint). The RunInfo carries the resume meta.
+func TestCheckpoint_SingleLoopSaveAndComplete(t *testing.T) {
+	models, _ := phaseProvider(t, fake.Reply("done"))
+	cp := &fakeCheckpointer{}
+	f := &fakeCheckpointFactory{cp: cp}
+	ex := New(Config{Registry: tool.NewRegistry(), Models: models, Ports: Ports{Checkpointer: f}})
+
+	res := ex.Run(context.Background(),
+		RunnableAgent{ID: "a1", Name: "boss", ModelTier: "test-model"},
+		tool.Invocation{RunID: "run-x", CallerID: "steve", ChannelID: "chan", GuildID: "g", SkillInputs: map[string]any{"prompt": "go"}},
+		"go")
+	if res.Err != nil {
+		t.Fatalf("run error: %v", res.Err)
+	}
+	if f.info.RunID != "run-x" || f.info.SubjectID != "a1" || f.info.ModelTier != "test-model" || f.info.GuildID != "g" {
+		t.Errorf("Begin RunInfo missing resume meta: %+v", f.info)
+	}
+	if len(cp.saves) == 0 {
+		t.Error("expected at least one checkpoint Save during the run")
+	} else if len(cp.saves[len(cp.saves)-1].Messages) == 0 {
+		t.Error("checkpoint Save should carry the running transcript")
+	}
+	if !cp.completed {
+		t.Error("a successful run must Complete (clear) its checkpoint")
+	}
+	if cp.failed {
+		t.Error("a successful run must NOT Fail its checkpoint")
+	}
+}
+
+// TestCheckpoint_TerminalErrorFails: a run that errors (not shutdown) Fails its
+// checkpoint (clears it — not a recovery candidate).
+func TestCheckpoint_TerminalErrorFails(t *testing.T) {
+	models, _ := phaseProvider(t, fake.Fail(errors.New("model down")))
+	cp := &fakeCheckpointer{}
+	ex := New(Config{Registry: tool.NewRegistry(), Models: models, Ports: Ports{Checkpointer: &fakeCheckpointFactory{cp: cp}}})
+
+	res := ex.Run(context.Background(),
+		RunnableAgent{ID: "a1", ModelTier: "test-model"},
+		tool.Invocation{RunID: "r", CallerID: "c", SkillInputs: map[string]any{"prompt": "go"}}, "go")
+	if res.Err == nil {
+		t.Fatal("expected a run error")
+	}
+	if !cp.failed {
+		t.Error("a terminal (non-shutdown) error must Fail the checkpoint")
+	}
+	if cp.completed {
+		t.Error("a failed run must NOT Complete its checkpoint")
+	}
+}
+
+// TestCheckpoint_ResumeSeedsHistory: a run carrying a ResumeState seeds the saved
+// transcript as the model's opening messages (continues) instead of the input.
+func TestCheckpoint_ResumeSeedsHistory(t *testing.T) {
+	models, fp := phaseProvider(t, fake.Reply("continued"))
+	history := []llm.Message{llm.UserText("prior turn 1"), llm.AssistantText("prior answer 1")}
+	ctx := WithResumeState(context.Background(), &ResumeState{History: history})
+
+	ex := New(Config{Registry: tool.NewRegistry(), Models: models})
+	res := ex.Run(ctx,
+		RunnableAgent{ID: "a1", ModelTier: "test-model"},
+		tool.Invocation{RunID: "r", CallerID: "c", SkillInputs: map[string]any{"prompt": "ignored-on-resume"}}, "ignored-on-resume")
+	if res.Err != nil {
+		t.Fatalf("run error: %v", res.Err)
+	}
+	got := fp.Calls()[0].Request.Messages
+	if len(got) != len(history) {
+		t.Fatalf("resume should seed the saved %d-message transcript, got %d messages", len(history), len(got))
+	}
+}
+
+// TestCheckpoint_PhaseBoundarySavesCompleted: a durable multi-phase run records
+// the completed phases at each boundary, growing the list, and Completes on
+// success.
+func TestCheckpoint_PhaseBoundarySavesCompleted(t *testing.T) {
+	models, _ := phaseProvider(t, fake.Reply("out-a"), fake.Reply("out-b"))
+	cp := &fakeCheckpointer{}
+	ex := New(Config{Registry: tool.NewRegistry(), Models: models, Ports: Ports{Checkpointer: &fakeCheckpointFactory{cp: cp}}})
+
+	ra := RunnableAgent{
+		ID: "p", ModelTier: "test-model",
+		Phases: []Phase{{Name: "a", SystemPrompt: "A"}, {Name: "b", SystemPrompt: "B"}},
+	}
+	if res := ex.Run(context.Background(), ra, tool.Invocation{RunID: "r", CallerID: "c"}, "Q"); res.Err != nil {
+		t.Fatalf("run error: %v", res.Err)
+	}
+	// The final phase-boundary Save must list both completed phases.
+	var lastPhaseSave *RunCheckpointState
+	for i := range cp.saves {
+		if len(cp.saves[i].CompletedPhases) > 0 {
+			lastPhaseSave = &cp.saves[i]
+		}
+	}
+	if lastPhaseSave == nil || len(lastPhaseSave.CompletedPhases) != 2 {
+		t.Fatalf("expected a phase-boundary Save listing 2 completed phases; saves=%+v", cp.saves)
+	}
+	if !cp.completed {
+		t.Error("a successful phased run must Complete its checkpoint")
+	}
+}
+
+// TestCheckpoint_ResumeSkipsCompletedPhases: a resumed multi-phase run skips
+// phases already in ResumeState.CompletedPhases (only the remaining phase calls
+// the model) and threads their outputs into the remaining phase's template.
+func TestCheckpoint_ResumeSkipsCompletedPhases(t *testing.T) {
+	models, fp := phaseProvider(t, fake.Reply("out-b")) // ONLY phase b should call the model
+	ctx := WithResumeState(context.Background(), &ResumeState{
+		CompletedPhases: []PhaseOutput{{Name: "a", Output: "saved-a"}},
+	})
+	ex := New(Config{Registry: tool.NewRegistry(), Models: models})
+
+	ra := RunnableAgent{
+		ID: "p", ModelTier: "test-model",
+		Phases: []Phase{
+			{Name: "a", SystemPrompt: "A"},
+			{Name: "b", SystemPrompt: "B saw {{.a}}"},
+		},
+	}
+	res := ex.Run(ctx, ra, tool.Invocation{RunID: "r", CallerID: "c"}, "Q")
+	if res.Err != nil {
+		t.Fatalf("run error: %v", res.Err)
+	}
+	if res.Output != "out-b" {
+		t.Fatalf("output = %q, want out-b", res.Output)
+	}
+	calls := fp.Calls()
+	if len(calls) != 1 {
+		t.Fatalf("only the un-completed phase b should call the model; got %d calls", len(calls))
+	}
+	if calls[0].Request.System != "B saw saved-a" {
+		t.Errorf("resumed phase b should see the completed phase a's saved output; system = %q", calls[0].Request.System)
+	}
+}

run/executor.go

@@ -165,7 +165,9 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 		Name:          ra.Name,
 		CallerID:      inv.CallerID,
 		ChannelID:     inv.ChannelID,
+		GuildID:       inv.GuildID,
 		ParentRunID:   inv.ParentRunID,
+		ModelTier:     tier,
 		Inputs:        inv.SkillInputs,
 		StartedAt:     started,
 		MaxIterations: maxIter,
@@ -180,6 +182,19 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 		inv.RunState = stateAcc
 	}
 
+	// Durable recovery (optional): a recovered run carries a ResumeState (prior
+	// transcript / completed phases) + an existing Checkpointer in ctx so it
+	// continues on the SAME durable record; a fresh run mints a per-run
+	// Checkpointer via the factory (which decides durability — nil = non-durable).
+	// nil-safe throughout.
+	resume := resumeStateFromContext(ctx)
+	ckpt := existingCheckpointerFromContext(ctx)
+	if ckpt == nil && e.cfg.Ports.Checkpointer != nil {
+		if c, cerr := e.cfg.Ports.Checkpointer.Begin(ctx, info); cerr == nil {
+			ckpt = c
+		}
+	}
+
 	// Steer mailbox: lets session tools (via inv.AttachImages) feed multimodal
 	// messages into the running conversation before its next step. Created BEFORE
 	// the toolbox build so any tool's handler captures the live AttachImages seam.
@@ -289,11 +304,11 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 	}
 
 	// Shared agent options used by BOTH the single-loop path and every phase: the
-	// tool-error guards, the step observer, and optional compaction. The toolbox +
-	// step ceiling are NOT shared (they vary per phase), so they're added per path.
+	// tool-error guards and optional compaction. The toolbox, step ceiling, AND
+	// step observer are added per path (the observer is wrapped for checkpointing,
+	// which differs single-loop vs per-phase).
 	sharedOpts := []agent.Option{
 		agent.WithToolErrorLimits(e.cfg.Defaults.MaxConsecutiveToolErrors, e.cfg.Defaults.MaxSameToolCallRepeats),
-		agent.WithStepObserver(stepObserver),
 	}
 	if e.cfg.Compactor != nil && e.cfg.ContextTokens != nil {
 		if threshold := e.compactionThreshold(tier); threshold > 0 {
@@ -330,18 +345,47 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 		// Single-loop run: the agent's base prompt + full toolbox, with the
 		// critic's DYNAMIC step ceiling (WithMaxStepsFunc, so it can raise a
 		// healthy-but-long run's budget mid-flight; falls back to maxIter).
+		//
+		// Checkpointing: wrap the step observer to accumulate the running transcript
+		// and Save it each step (the host throttles). A recovered run seeds the saved
+		// transcript as history and continues with no new input. acc starts from the
+		// resume history (or the opening user message) and grows as steps complete.
+		obs := stepObserver
+		if ckpt != nil {
+			acc := []llm.Message{multimodalUserMessage(input, inv.Images)}
+			if resume != nil && len(resume.History) > 0 {
+				acc = append([]llm.Message(nil), resume.History...)
+			}
+			obs = func(s agent.Step) {
+				stepObserver(s)
+				if s.Response != nil {
+					acc = append(acc, s.Response.Message())
+				}
+				if len(s.Results) > 0 {
+					acc = append(acc, llm.ToolResultsMessage(s.Results...))
+				}
+				_ = ckpt.Save(runCtx, RunCheckpointState{Messages: acc, Iteration: s.Index + 1})
+			}
+		}
 		opts := append([]agent.Option{
 			agent.WithToolbox(toolbox),
 			critic.maxStepsOption(maxIter),
+			agent.WithStepObserver(obs),
 		}, sharedOpts...)
 		ag := agent.New(model, e.systemPrompt(ra), opts...)
+		if resume != nil && len(resume.History) > 0 {
+			// Resume: seed the saved transcript and continue (no new input — the
+			// completed tool calls in the transcript are NOT re-run).
+			runRes, runErr = ag.Run(runCtx, "", agent.WithSteer(steer), agent.WithHistory(resume.History))
+		} else {
 			runRes, runErr = runAgent(runCtx, ag, input, inv.Images, agent.WithSteer(steer))
+		}
 	} else {
 		// Multi-phase pipeline: each phase runs its own prompt/tier/tools/step-cap
-		// sequentially, threading outputs through {{.<PhaseName>}} templates. Reuses
-		// the shared opts so audit/steps/critic-steer accumulate across every phase.
-		// (Per-phase step caps are fixed — the critic's dynamic ceiling is not
-		// propagated to phases — but its steer + hard deadline still apply.)
+		// sequentially, threading outputs through {{.<PhaseName>}} templates. The
+		// shared step observer (audit/steps/critic) is wired per phase by the phase
+		// runner; checkpointing is phase-boundary granular (completed phases are
+		// recorded so a resumed run skips them).
 		runRes, runErr = e.runPhases(runCtx, ra, phaseDeps{
 			baseModel:    model,
 			baseToolbox:  toolbox,
@@ -350,9 +394,15 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 			stepObserver: stepObserver,
 			steer:        steer,
 			rec:          rec,
+			checkpointer: ckpt,
+			resume:       resume,
 		}, input, inv.Images)
 	}
 
+	// Finalize durable recovery: clear the checkpoint on success/terminal failure,
+	// or leave it for boot recovery when the run was interrupted by shutdown.
+	finalizeCheckpoint(ctx, ckpt, runErr, context.Cause(runCtx))
+
 	status := statusFor(runCtx, runErr)
 	if runRes != nil {
 		res.Output = runRes.Output

run/phases.go

@@ -64,6 +64,13 @@ type phaseDeps struct {
 	stepObserver func(agent.Step)
 	steer        func() []llm.Message
 	rec          RunRecorder
+	// checkpointer records phase-boundary progress (completed phases) for durable
+	// recovery; nil = non-durable. resume carries a recovered run's completed
+	// phases so they are skipped on re-run. Phase recovery is boundary-granular:
+	// the interrupted (active) phase re-runs from its start (its mid-phase
+	// transcript is NOT resumed — only the single-loop path resumes mid-loop).
+	checkpointer Checkpointer
+	resume       *ResumeState
 }
 
 // runPhases executes ra.Phases sequentially and returns a synthetic agent.Result
@@ -73,10 +80,22 @@ type phaseDeps struct {
 // deadline/critic-kill — returns the error.
 func (e *Executor) runPhases(runCtx context.Context, ra RunnableAgent, deps phaseDeps, query string, images []llm.ImagePart) (*agent.Result, error) {
 	outputs := make(map[string]string, len(ra.Phases))
+	var completed []PhaseOutput
 	var lastResult *agent.Result
 	var lastOutput string
 	var totalUsage llm.Usage
 
+	// Resume: pre-populate from the saved checkpoint so already-finished phases are
+	// skipped. The interrupted (active) phase is NOT pre-populated, so it re-runs
+	// from its start (boundary-granular recovery).
+	if deps.resume != nil {
+		for _, pc := range deps.resume.CompletedPhases {
+			outputs[pc.Name] = pc.Output
+			completed = append(completed, pc)
+			lastOutput = pc.Output
+		}
+	}
+
 	// finish stamps the aggregated usage + final output onto the synthetic result.
 	finish := func(err error) (*agent.Result, error) {
 		if lastResult == nil {
@@ -90,6 +109,12 @@ func (e *Executor) runPhases(runCtx context.Context, ra RunnableAgent, deps phas
 	}
 
 	for i, phase := range ra.Phases {
+		// Skip phases already completed on a resumed run (key presence, not output
+		// emptiness — a legitimately-empty phase output still counts as done).
+		if _, done := outputs[phase.Name]; done {
+			lastOutput = outputs[phase.Name]
+			continue
+		}
 		// A killed/timed-out/cancelled run must not start its next phase.
 		if err := runCtx.Err(); err != nil {
 			return finish(err)
@@ -151,6 +176,16 @@ func (e *Executor) runPhases(runCtx context.Context, ra RunnableAgent, deps phas
 
 		outputs[phase.Name] = output
 		lastOutput = output
+		// Checkpoint the phase boundary: this phase is done, so a resumed run skips
+		// it and continues from the next. (Copy the slice — the checkpointer may
+		// hold/serialize it asynchronously.)
+		completed = append(completed, PhaseOutput{Name: phase.Name, Output: output})
+		if deps.checkpointer != nil {
+			_ = deps.checkpointer.Save(runCtx, RunCheckpointState{
+				CompletedPhases: append([]PhaseOutput(nil), completed...),
+				ActivePhase:     "",
+			})
+		}
 	}
 
 	return finish(nil)
@@ -192,11 +227,13 @@ func (e *Executor) runOnePhase(runCtx context.Context, ra RunnableAgent, deps ph
 		maxIter = deps.baseMaxIter
 	}
 	// Per-phase opts: a fixed step ceiling for this phase (the critic's dynamic
-	// ceiling is intentionally not propagated to phases) + the phase toolbox, on
-	// top of the shared opts (tool-error limits, step observer, compactor).
+	// ceiling is intentionally not propagated to phases) + the phase toolbox + the
+	// shared step observer (audit/steps/critic), on top of the shared opts
+	// (tool-error limits, compactor).
 	opts := append([]agent.Option{
 		agent.WithToolbox(toolbox),
 		agent.WithMaxSteps(maxIter),
+		agent.WithStepObserver(deps.stepObserver),
 	}, deps.sharedOpts...)
 	ag := agent.New(model, system, opts...)
 

run/ports.go

@@ -33,9 +33,10 @@ type Ports struct {
 	Budget Budget
 	// Critic optionally monitors a long run for hangs/runaways. nil = none.
 	Critic Critic
-	// Checkpointer persists resumable progress for durable recovery. nil = no
-	// checkpointing (a run interrupted by shutdown is simply lost).
-	Checkpointer Checkpointer
+	// Checkpointer mints a per-run Checkpointer for durable recovery (it decides
+	// per run whether the run is durable). nil = no checkpointing (a run
+	// interrupted by shutdown is simply lost).
+	Checkpointer CheckpointerFactory
 	// Palette resolves SkillPalette / SubAgentPalette entries into delegation
 	// tools (skill__<name> / agent__<name>). nil = those entries are inert.
 	Palette PaletteSource
@@ -66,7 +67,9 @@ type RunInfo struct {
 	Name        string
 	CallerID    string
 	ChannelID   string
+	GuildID     string // the originating guild/server id (empty for DMs/triggers)
 	ParentRunID string
+	ModelTier   string // the run's resolved base tier (for checkpoint re-dispatch)
 	Inputs      map[string]any
 	StartedAt   time.Time
 	// MaxIterations is the run's base tool-dispatch step ceiling, so a critic can
@@ -172,6 +175,16 @@ type CriticHandle interface {
 
 // --- Checkpointer ---
 
+// CheckpointerFactory decides, per run, whether the run is durable and (if so)
+// mints the per-run Checkpointer that records its progress. It returns (nil, nil)
+// for a non-durable run (the common short-run case — no checkpointing overhead).
+// A storage error should be logged and degraded to (nil, nil) so a failing
+// checkpoint store never fails the run. Mirrors mort's
+// agentexec.CheckpointerFactory.
+type CheckpointerFactory interface {
+	Begin(ctx context.Context, info RunInfo) (Checkpointer, error)
+}
+
 // Checkpointer persists a run's resumable progress for durable recovery.
 // Mirrors mort's agentexec.RunCheckpointer.
 type Checkpointer interface {
@@ -184,11 +197,24 @@ type Checkpointer interface {
 	Fail(ctx context.Context, err error) error
 }
 
-// RunCheckpointState is the resumable snapshot a Checkpointer persists. Kept
-// minimal here; the executor extends what it records during the merge.
+// RunCheckpointState is the resumable snapshot a Checkpointer persists.
 type RunCheckpointState struct {
+	// Messages is the running transcript (single-loop run) OR the active phase's
+	// transcript (multi-phase run). May be nil.
 	Messages  []llm.Message
 	Iteration int
+	// CompletedPhases is set only for multi-phase runs: the outputs of phases
+	// already finished, in phase order. nil for single-loop runs.
+	CompletedPhases []PhaseOutput
+	// ActivePhase is the name of the in-progress phase (multi-phase only).
+	ActivePhase string
+}
+
+// PhaseOutput is one completed pipeline phase's name and output text, recorded in
+// a checkpoint so a resumed multi-phase run can skip already-finished phases.
+type PhaseOutput struct {
+	Name   string
+	Output string
 }
 
 // --- PaletteSource ---