diff --git a/internal/api/server.go b/internal/api/server.go
index d9eadf2..021819c 100644
--- a/internal/api/server.go
+++ b/internal/api/server.go
@@ -320,9 +320,16 @@ func (d Deps) handleIngestDocument(w http.ResponseWriter, r *http.Request) {
 		SourceRef:   key,
 	})
 	if err := d.Queue.Enqueue(ctx, queue.Job{
-		Kind:      queue.KindIngestDocument,
-		Payload:   payload,
-		DedupeKey: string(docID),
+		Kind:    queue.KindIngestDocument,
+		Payload: payload,
+		// Cap retries so a transient failure (e.g. a parse-timeout or a
+		// not-yet-visible source under heavy concurrent ingestion) gets a
+		// few chances to recover, without the queue's default 25-attempt
+		// exponential backoff dragging a genuinely-bad document out for
+		// hours. The document stays "parsing" across these attempts and
+		// only flips to "failed" on the last one (see Pipeline.fail).
+		MaxRetries: 5,
+		DedupeKey:  string(docID),
 	}); err != nil {
 		d.Logger.Error("ingest: enqueue failed", "err", err)
 		writeErr(w, http.StatusInternalServerError, "enqueue failed")
diff --git a/pkg/ingest/ingest.go b/pkg/ingest/ingest.go
index 78647a4..9d97507 100644
--- a/pkg/ingest/ingest.go
+++ b/pkg/ingest/ingest.go
@@ -317,6 +317,26 @@ func (p *Pipeline) acquireGlobalLLM(ctx context.Context) (release func(), ok boo
 	}
 }
 
+// lastAttemptCtxKey carries whether the current ingest job is on its final
+// queue attempt. When it isn't, a transient failure must NOT be surfaced as a
+// terminal "failed" status — the queue will retry it.
+type lastAttemptCtxKeyT struct{}
+
+func withLastAttempt(ctx context.Context, last bool) context.Context {
+	return context.WithValue(ctx, lastAttemptCtxKeyT{}, last)
+}
+
+// isLastAttempt reports whether this is the final attempt. Defaults to true
+// when unset (callers that don't track attempts, e.g. tests, keep the
+// fail-immediately behaviour).
+func isLastAttempt(ctx context.Context) bool {
+	v, ok := ctx.Value(lastAttemptCtxKeyT{}).(bool)
+	if !ok {
+		return true
+	}
+	return v
+}
+
 // Handler returns a queue.Handler suitable for queue.KindIngestDocument.
 func (p *Pipeline) Handler() queue.Handler {
 	return func(ctx context.Context, j queue.Job) error {
@@ -324,7 +344,11 @@ func (p *Pipeline) Handler() queue.Handler {
 		if err := json.Unmarshal(j.Payload, &payload); err != nil {
 			return fmt.Errorf("decode payload: %w", err)
 		}
-		return p.Run(ctx, payload)
+		// A job with no attempt tracking (MaxAttempts<=0) is treated as its
+		// own last attempt; otherwise it's the last attempt only when the
+		// queue has used up its retries.
+		last := j.MaxAttempts <= 0 || j.Attempt >= j.MaxAttempts
+		return p.Run(withLastAttempt(ctx, last), payload)
 	}
 }
 
@@ -1005,11 +1029,30 @@ func fallbackSummary(title, body string) string {
 
 func (p *Pipeline) fail(ctx context.Context, store docPersister, id tree.DocumentID, stage string, cause error) {
 	msg := fmt.Sprintf("%s: %s", stage, cause.Error())
-	// Use a FRESH context for the failure write — the inbound one is
-	// almost certainly the reason we're failing (timeout/cancel) and
-	// reusing it would leave the doc stuck on "parsing" forever.
+	// Use a FRESH context for the status write — the inbound one is almost
+	// certainly the reason we're failing (timeout/cancel) and reusing it
+	// would leave the doc stuck mid-flight.
 	failCtx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
 	defer cancel()
+
+	// If the queue will retry this job, the failure is (so far) transient —
+	// under heavy concurrent ingestion, parse can hit a parse-timeout or a
+	// not-yet-visible source and recover on a later attempt. Surfacing
+	// "failed" now would tell a polling client the document is dead when it
+	// isn't, so keep it in "parsing" and let the retry run. Only the final
+	// attempt produces a terminal "failed".
+	if !isLastAttempt(ctx) {
+		p.Logger.Warn("ingest: transient failure, will retry",
+			"document_id", string(id), "stage", stage, "cause", cause.Error())
+		if err := store.SetDocumentStatus(failCtx, id, db.StatusParsing, ""); err != nil {
+			p.Logger.Error("ingest: failed to reset document to parsing", "err", err)
+		}
+		return
+	}
+
+	// Terminal failure: log it (previously silent — failures only showed up
+	// in the DB error_message) and mark the document failed.
+	p.Logger.Error("ingest: failed", "document_id", string(id), "stage", stage, "cause", cause.Error())
 	if err := store.SetDocumentStatus(failCtx, id, db.StatusFailed, msg); err != nil {
 		p.Logger.Error("ingest: failed to mark document failed", "err", err, "cause", cause)
 	}
diff --git a/pkg/queue/queue.go b/pkg/queue/queue.go
index d5285e8..45e0380 100644
--- a/pkg/queue/queue.go
+++ b/pkg/queue/queue.go
@@ -44,6 +44,15 @@ type Job struct {
 
 	// Optional: max retries before dead-lettering.
 	MaxRetries int `json:"max_retries,omitempty"`
+
+	// Attempt is the 1-based current attempt number, set by the queue when
+	// it dispatches a job to its handler (0 if the queue doesn't track
+	// attempts). MaxAttempts is the total before dead-lettering. Handlers
+	// use these to tell a transient, will-be-retried failure apart from a
+	// terminal one — e.g. so a document isn't marked "failed" while the
+	// queue will still retry it.
+	Attempt     int `json:"-"`
+	MaxAttempts int `json:"-"`
 }
 
 // Handler processes a single job.
diff --git a/pkg/queue/river.go b/pkg/queue/river.go
index 282ceda..5d45859 100644
--- a/pkg/queue/river.go
+++ b/pkg/queue/river.go
@@ -73,7 +73,19 @@ func (w *envelopeWorker) Work(ctx context.Context, job *river.Job[envelopeArgs])
 	if !ok {
 		return fmt.Errorf("%w: %q", ErrUnknownKind, job.Args.DomainKind)
 	}
-	return h(ctx, Job{Kind: job.Args.DomainKind, Payload: job.Args.Payload})
+	// Attempt/MaxAttempts live on River's embedded *JobRow, which is always
+	// populated in production but may be nil in unit tests that construct a
+	// bare river.Job. Guard the deref.
+	attempt, maxAttempts := 0, 0
+	if job.JobRow != nil {
+		attempt, maxAttempts = job.Attempt, job.MaxAttempts
+	}
+	return h(ctx, Job{
+		Kind:        job.Args.DomainKind,
+		Payload:     job.Args.Payload,
+		Attempt:     attempt,
+		MaxAttempts: maxAttempts,
+	})
 }
 
 // NewRiver constructs a new River-backed Queue. It opens its own pgxpool