diff --git a/checkpoint/checkpoint.go b/checkpoint/checkpoint.go
index 52411e2..576584e 100644
--- a/checkpoint/checkpoint.go
+++ b/checkpoint/checkpoint.go
@@ -35,10 +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 (single-loop or active phase)
+	Messages        []llm.Message     // conversation so far (single-loop runs)
 	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
 }
 
diff --git a/checkpoint/handle.go b/checkpoint/handle.go
index eba2dfe..d231485 100644
--- a/checkpoint/handle.go
+++ b/checkpoint/handle.go
@@ -58,7 +58,6 @@ func (h *handle) Save(ctx context.Context, st run.RunCheckpointState) error {
 		Messages:        st.Messages,
 		Iteration:       st.Iteration,
 		CompletedPhases: st.CompletedPhases,
-		ActivePhase:     st.ActivePhase,
 		UpdatedAt:       now,
 	}); err != nil {
 		return err
@@ -92,7 +91,6 @@ func (noop) Fail(context.Context, error) error                  { return nil }
 type factory struct {
 	store    CheckpointStore
 	throttle time.Duration
-	now      func() time.Time
 }
 
 var _ run.CheckpointerFactory = (*factory)(nil)
@@ -119,5 +117,5 @@ func (f *factory) Begin(_ context.Context, info run.RunInfo) (run.Checkpointer,
 		ModelTier:   info.ModelTier,
 		ParentRunID: info.ParentRunID,
 	}
-	return New(f.store, meta, f.throttle, f.now), nil
+	return New(f.store, meta, f.throttle, nil /* now defaults to time.Now */), nil
 }
diff --git a/run/checkpoint.go b/run/checkpoint.go
index 0aeb079..8c266c5 100644
--- a/run/checkpoint.go
+++ b/run/checkpoint.go
@@ -3,6 +3,7 @@ package run
 import (
 	"context"
 	"errors"
+	"log/slog"
 
 	"gitea.stevedudenhoeffer.com/steve/majordomo/llm"
 )
@@ -17,12 +18,14 @@ import (
 
 // 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).
+// WithResumeState; the executor reads it:
+//   - single-loop: History seeds the saved transcript (the run continues).
+//   - multi-phase: CompletedPhases are skipped; the interrupted phase re-runs
+//     from its start (boundary-granular — there is no mid-phase transcript
+//     resume, so History is unused for multi-phase runs).
 type ResumeState struct {
-	History         []llm.Message // single-loop transcript OR active-phase transcript
+	History         []llm.Message // single-loop transcript (unused for multi-phase)
 	CompletedPhases []PhaseOutput // multi-phase: outputs of finished phases, in order
-	ActivePhase     string        // multi-phase: the phase that was in flight
 }
 
 type resumeStateKey struct{}
@@ -79,15 +82,21 @@ func classifyCheckpointOutcome(runErr, cause error) checkpointOutcome {
 
 // 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.
+// Complete/Fail errors are best-effort but logged (a stale record would only
+// cause a wasteful boot-recovery retry, not data loss).
 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))
+		if err := cp.Complete(detach(ctx)); err != nil {
+			slog.Warn("run: checkpoint Complete failed", "error", err)
+		}
 	case checkpointFail:
-		_ = cp.Fail(detach(ctx), runErr)
+		if err := cp.Fail(detach(ctx), runErr); err != nil {
+			slog.Warn("run: checkpoint Fail failed", "error", err)
+		}
 	case checkpointLeaveRunning:
 		// Interrupted by shutdown: leave the record for boot recovery.
 	}
diff --git a/run/executor.go b/run/executor.go
index 055957c..c950f98 100644
--- a/run/executor.go
+++ b/run/executor.go
@@ -4,6 +4,7 @@ import (
 	"context"
 	"errors"
 	"fmt"
+	"log/slog"
 	"time"
 
 	"gitea.stevedudenhoeffer.com/steve/majordomo/agent"
@@ -113,13 +114,26 @@ type Result struct {
 func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocation, input string) (res Result) {
 	started := time.Now()
 	res = Result{RunID: inv.RunID}
+	// ckpt is the per-run durable checkpointer (resolved below; nil = non-durable).
+	// checkpointCause yields the run context's cancellation cause once the run
+	// context exists; nil before then (an early build-error return).
+	var ckpt Checkpointer
+	var checkpointCause func() error
 	// Enforce the no-panic contract: a panic anywhere in the run (incl. a host
 	// Critic/Audit/Palette callback on the main goroutine) becomes Result.Err
-	// rather than unwinding into the caller.
+	// rather than unwinding into the caller. This defer ALSO finalizes the
+	// checkpoint on EVERY exit path — panic, an early build-error return (before
+	// the run loop), or normal completion — so a recovered run's durable record is
+	// never left dangling (which would loop boot-recovery on a persistent error).
 	defer func() {
 		if r := recover(); r != nil {
 			res.Err = fmt.Errorf("run.Executor: recovered panic: %v", r)
 		}
+		var cause error
+		if checkpointCause != nil {
+			cause = checkpointCause()
+		}
+		finalizeCheckpoint(ctx, ckpt, res.Err, cause)
 	}()
 
 	tier := ra.ModelTier
@@ -188,9 +202,15 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 	// Checkpointer via the factory (which decides durability — nil = non-durable).
 	// nil-safe throughout.
 	resume := resumeStateFromContext(ctx)
-	ckpt := existingCheckpointerFromContext(ctx)
+	ckpt = existingCheckpointerFromContext(ctx)
 	if ckpt == nil && e.cfg.Ports.Checkpointer != nil {
-		if c, cerr := e.cfg.Ports.Checkpointer.Begin(ctx, info); cerr == nil {
+		c, cerr := e.cfg.Ports.Checkpointer.Begin(ctx, info)
+		if cerr != nil {
+			// Degrade to non-durable (the documented contract) but log it — a
+			// failing checkpoint store must not fail the run, yet shouldn't be silent.
+			slog.Warn("run: checkpointer Begin failed; running non-durable",
+				"run_id", inv.RunID, "error", cerr)
+		} else {
 			ckpt = c
 		}
 	}
@@ -262,6 +282,9 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 	defer cancelCause(nil)
 	runCtx, mergeCancel := MergeCancellation(runCtx, ctx)
 	defer mergeCancel()
+	// The finalize defer (top of Run) now has a run context to read the
+	// cancellation cause from (shutdown vs critic-kill vs deadline vs cancel).
+	checkpointCause = func() error { return context.Cause(runCtx) }
 
 	// Critic (optional): monitors the run for a stall, can nudge/extend/kill via
 	// its host Escalator. Its hard deadline is bound to runCtx (cancel on pass).
@@ -339,6 +362,8 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 	// the critic's nudges before each step.
 	steer := func() []llm.Message { return append(mailbox.drain(), critic.drainSteer()...) }
 
+	resuming := resume != nil && len(resume.History) > 0
+
 	var runRes *agent.Result
 	var runErr error
 	if len(ra.Phases) == 0 {
@@ -347,14 +372,19 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 		// 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.
+		// and Save it each step. Save is called every step; THROTTLING is the
+		// Checkpointer's responsibility (the battery + mort's durable-job adapter
+		// both throttle + size-cap), so the kernel doesn't gate the hot path. The
+		// accumulated transcript is the pre-compaction one (the observer sees raw
+		// step responses, not the loop's compacted history) — a host that caps size
+		// bounds it. A recovered run seeds the saved transcript and continues.
 		obs := stepObserver
 		if ckpt != nil {
-			acc := []llm.Message{multimodalUserMessage(input, inv.Images)}
-			if resume != nil && len(resume.History) > 0 {
+			var acc []llm.Message
+			if resuming {
 				acc = append([]llm.Message(nil), resume.History...)
+			} else {
+				acc = []llm.Message{multimodalUserMessage(input, inv.Images)}
 			}
 			obs = func(s agent.Step) {
 				stepObserver(s)
@@ -373,7 +403,7 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 			agent.WithStepObserver(obs),
 		}, sharedOpts...)
 		ag := agent.New(model, e.systemPrompt(ra), opts...)
-		if resume != nil && len(resume.History) > 0 {
+		if resuming {
 			// 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))
@@ -399,9 +429,8 @@ func (e *Executor) Run(ctx context.Context, ra RunnableAgent, inv tool.Invocatio
 		}, 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))
+	// Durable-recovery finalize (Complete/Fail/leave-running) happens in the
+	// top-of-Run defer so it covers panics + early build-error returns too.
 
 	status := statusFor(runCtx, runErr)
 	if runRes != nil {
diff --git a/run/phases.go b/run/phases.go
index 4a25d9c..4a73d89 100644
--- a/run/phases.go
+++ b/run/phases.go
@@ -53,9 +53,10 @@ import (
 
 // phaseDeps carries the per-run state the phase runner shares with Run: the base
 // model, the full decorated toolbox (filtered per phase), the base step cap, the
-// shared agent options (tool-error limits + step observer + compactor), the
-// shared step observer (also fed by IsRunFunc bare calls), the critic/session
-// steer, and the audit recorder (phase events).
+// shared agent options (tool-error limits + compactor — the step observer is
+// added per phase, NOT in sharedOpts, so checkpointing can vary per path), the
+// shared step observer (wired into each phase's loop AND invoked for IsRunFunc
+// bare calls), the critic/session steer, and the audit recorder (phase events).
 type phaseDeps struct {
 	baseModel    llm.Model
 	baseToolbox  *llm.Toolbox
@@ -85,12 +86,18 @@ func (e *Executor) runPhases(runCtx context.Context, ra RunnableAgent, deps phas
 	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).
+	// resumeSkip is the set of phases already finished on a RECOVERED run — kept
+	// SEPARATE from the live `outputs` map (which fills as phases run this time) so
+	// the skip guard only skips RESUME-completed phases, never a fresh run's own
+	// phases. (Reusing `outputs` would make a second phase with a duplicate name
+	// skip itself.) Pre-populate outputs + completed so a resumed run threads the
+	// saved outputs into later phases. The interrupted (active) phase is NOT
+	// pre-populated, so it re-runs from its start (boundary-granular recovery).
+	resumeSkip := map[string]bool{}
 	if deps.resume != nil {
 		for _, pc := range deps.resume.CompletedPhases {
 			outputs[pc.Name] = pc.Output
+			resumeSkip[pc.Name] = true
 			completed = append(completed, pc)
 			lastOutput = pc.Output
 		}
@@ -109,10 +116,8 @@ 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]
+		// Skip phases already completed on a resumed run.
+		if resumeSkip[phase.Name] {
 			continue
 		}
 		// A killed/timed-out/cancelled run must not start its next phase.
@@ -183,7 +188,6 @@ func (e *Executor) runPhases(runCtx context.Context, ra RunnableAgent, deps phas
 		if deps.checkpointer != nil {
 			_ = deps.checkpointer.Save(runCtx, RunCheckpointState{
 				CompletedPhases: append([]PhaseOutput(nil), completed...),
-				ActivePhase:     "",
 			})
 		}
 	}
diff --git a/run/phases_test.go b/run/phases_test.go
index a8fe249..454c71c 100644
--- a/run/phases_test.go
+++ b/run/phases_test.go
@@ -130,6 +130,26 @@ func TestPhases_OptionalDoesNotSwallowCancellation(t *testing.T) {
 	}
 }
 
+// TestPhases_DuplicateNamesBothRun: a fresh (non-resume) run with two phases
+// sharing a name must run BOTH — the resume-skip guard keys off a separate
+// resume set, not the live outputs map (which fills as phases run), so a phase
+// never skips a same-named sibling on a fresh run.
+func TestPhases_DuplicateNamesBothRun(t *testing.T) {
+	models, fp := phaseProvider(t, fake.Reply("first"), fake.Reply("second"))
+	ex := New(Config{Registry: tool.NewRegistry(), Models: models})
+	ra := RunnableAgent{
+		Name: "p", ModelTier: "test-model",
+		Phases: []Phase{{Name: "x", SystemPrompt: "P1"}, {Name: "x", SystemPrompt: "P2"}},
+	}
+	res := ex.Run(context.Background(), ra, tool.Invocation{RunID: "r"}, "Q")
+	if res.Err != nil {
+		t.Fatalf("run error: %v", res.Err)
+	}
+	if n := len(fp.Calls()); n != 2 {
+		t.Fatalf("both same-named phases must run on a fresh run; got %d model calls", n)
+	}
+}
+
 // TestPhases_HardErrorAborts: a NON-optional phase that hits a hard error (not a
 // budget/step exhaustion) aborts the pipeline; later phases do not run.
 func TestPhases_HardErrorAborts(t *testing.T) {
diff --git a/run/ports.go b/run/ports.go
index 6b59a74..9713cb6 100644
--- a/run/ports.go
+++ b/run/ports.go
@@ -199,15 +199,15 @@ type Checkpointer interface {
 
 // 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 is the running transcript of a SINGLE-LOOP run (grows each step;
+	// resumed via WithHistory). nil for multi-phase runs — phase recovery is
+	// boundary-granular (see CompletedPhases), not mid-phase transcript.
 	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.
+	// already finished, in phase order, so a resumed run skips them and re-runs
+	// the interrupted phase from its start. 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