diff --git a/ingestion/cmd/server/main.go b/ingestion/cmd/server/main.go
index 53baf1d..145fef7 100644
--- a/ingestion/cmd/server/main.go
+++ b/ingestion/cmd/server/main.go
@@ -32,6 +32,7 @@ import (
 	"github.com/mathiasbq/hyperguild/ingestion/internal/pipeline"
 	"github.com/mathiasbq/hyperguild/ingestion/internal/reranker"
 	"github.com/mathiasbq/hyperguild/ingestion/internal/search"
+	"github.com/mathiasbq/hyperguild/ingestion/internal/startupretry"
 	"github.com/mathiasbq/hyperguild/ingestion/internal/vectorstore"
 	"github.com/mathiasbq/hyperguild/ingestion/internal/watcher"
 	"github.com/mathiasbq/hyperguild/ingestion/internal/webhook"
@@ -314,6 +315,36 @@ func main() {
 	}
 
 	ctx := context.Background()
+
+	// Built before the watcher, the graph backfill and session ingestion, and
+	// retried rather than fatal (#83). Two separate reasons:
+	//
+	//   - On a cold cluster boot this pod can beat dex to serving and gets a
+	//     502 from ingress. Nothing is misconfigured; it simply started first.
+	//     Exiting there meant CrashLoopBackOff redoing the backfill on every
+	//     attempt, with exponential backoff stretching the brain outage.
+	//   - Constructing it first means a genuine config error (wrong issuer,
+	//     bad audience) fails in seconds instead of after all that work.
+	//
+	// The budget stays bounded: retrying forever would turn a misconfiguration
+	// into a process that looks alive and never serves.
+	jwtValidator, err := startupretry.Do(ctx,
+		startupretry.Policy{Attempts: 8, Base: time.Second, Max: 30 * time.Second},
+		func(ctx context.Context) (*chassisauth.JWTValidator, error) {
+			v, err := chassisauth.NewJWTValidator(ctx, os.Getenv("DEX_ISSUER_URL"), os.Getenv("MCP_AUDIENCE"))
+			if err != nil {
+				logger.Warn("oidc discovery not ready, retrying", "err", err)
+			}
+			return v, err
+		})
+	if err != nil {
+		logger.Error("build jwt validator", "err", err)
+		os.Exit(1)
+	}
+	if jwtValidator != nil {
+		logger.Info("jwt auth enabled", "issuer", os.Getenv("DEX_ISSUER_URL"))
+	}
+
 	if watchInterval > 0 {
 		watcher.Start(ctx, watcher.Config{
 			BrainDir: brainDir,
@@ -418,15 +449,6 @@ func main() {
 	if webhookHandler != nil {
 		mux.Handle("POST /webhooks/brain-sync", webhookHandler)
 	}
-	jwtValidator, err := chassisauth.NewJWTValidator(ctx, os.Getenv("DEX_ISSUER_URL"), os.Getenv("MCP_AUDIENCE"))
-	if err != nil {
-		logger.Error("build jwt validator", "err", err)
-		os.Exit(1)
-	}
-	if jwtValidator != nil {
-		logger.Info("jwt auth enabled", "issuer", os.Getenv("DEX_ISSUER_URL"))
-	}
-
 	// Resource-metadata URL is only emitted on 401 when Dex OAuth is
 	// configured. Static-Bearer-only deployments leave this empty so
 	// clients never see an OAuth challenge.
diff --git a/ingestion/internal/startupretry/startupretry.go b/ingestion/internal/startupretry/startupretry.go
new file mode 100644
index 0000000..2882f67
--- /dev/null
+++ b/ingestion/internal/startupretry/startupretry.go
@@ -0,0 +1,75 @@
+// Package startupretry retries a startup dependency that may not be serving
+// yet, instead of exiting on its first failure.
+//
+// It exists for the cold-boot ordering race (#83): on a cluster restart the
+// ingestion pod can reach OIDC discovery before dex is answering, gets a 502
+// from ingress, and dies — after having already connected postgres, backfilled
+// the graph and ingested session batches, all of which the restart redoes.
+// Nothing is misconfigured in that scenario; the pod simply started first.
+//
+// The budget is bounded on purpose. Retrying forever would turn a genuine
+// misconfiguration (wrong issuer URL, bad audience) into a process that looks
+// healthy and never serves, which is harder to diagnose than a crash loop.
+package startupretry
+
+import (
+	"context"
+	"fmt"
+	"time"
+)
+
+// Policy bounds the retry: at most Attempts calls, with the delay doubling
+// from Base and capped at Max.
+type Policy struct {
+	Attempts int           // total calls, including the first; < 1 means 1
+	Base     time.Duration // delay before the second attempt
+	Max      time.Duration // ceiling for the doubling delay
+}
+
+// Do calls fn until it succeeds, the attempt budget is spent, or ctx ends.
+//
+// The returned error wraps the last failure, so callers keep the diagnosis
+// they would have had without the retry.
+func Do[T any](ctx context.Context, p Policy, fn func(context.Context) (T, error)) (T, error) {
+	var zero T
+
+	attempts := p.Attempts
+	if attempts < 1 {
+		attempts = 1
+	}
+
+	delay := p.Base
+	var lastErr error
+
+	for i := range attempts {
+		if err := ctx.Err(); err != nil {
+			return zero, fmt.Errorf("startupretry: %w", err)
+		}
+
+		v, err := fn(ctx)
+		if err == nil {
+			return v, nil
+		}
+		lastErr = err
+
+		if i == attempts-1 {
+			break
+		}
+
+		if delay <= 0 {
+			delay = time.Second
+		}
+		if p.Max > 0 && delay > p.Max {
+			delay = p.Max
+		}
+
+		select {
+		case <-ctx.Done():
+			return zero, fmt.Errorf("startupretry: %w", ctx.Err())
+		case <-time.After(delay):
+		}
+		delay *= 2
+	}
+
+	return zero, fmt.Errorf("startupretry: gave up after %d attempts: %w", attempts, lastErr)
+}
diff --git a/ingestion/internal/startupretry/startupretry_test.go b/ingestion/internal/startupretry/startupretry_test.go
new file mode 100644
index 0000000..a96a017
--- /dev/null
+++ b/ingestion/internal/startupretry/startupretry_test.go
@@ -0,0 +1,144 @@
+// ingestion/internal/startupretry/startupretry_test.go
+package startupretry
+
+import (
+	"context"
+	"errors"
+	"testing"
+	"time"
+)
+
+func fastPolicy(attempts int) Policy {
+	return Policy{Attempts: attempts, Base: time.Millisecond, Max: 2 * time.Millisecond}
+}
+
+func TestDo_ReturnsImmediatelyOnFirstSuccess(t *testing.T) {
+	calls := 0
+	got, err := Do(context.Background(), fastPolicy(5), func(context.Context) (string, error) {
+		calls++
+		return "ready", nil
+	})
+
+	if err != nil {
+		t.Fatalf("Do: %v", err)
+	}
+	if got != "ready" {
+		t.Errorf("got %q, want %q", got, "ready")
+	}
+	if calls != 1 {
+		t.Errorf("calls = %d, want 1", calls)
+	}
+}
+
+func TestDo_SurvivesTransientFailuresThenSucceeds(t *testing.T) {
+	// The observed cold-boot race: dex is not serving yet, ingress answers
+	// 502 for the first few attempts, then discovery works.
+	calls := 0
+	got, err := Do(context.Background(), fastPolicy(5), func(context.Context) (string, error) {
+		calls++
+		if calls < 4 {
+			return "", errors.New("oidc discovery: status 502")
+		}
+		return "ready", nil
+	})
+
+	if err != nil {
+		t.Fatalf("Do returned %v — a transient 502 must not be fatal", err)
+	}
+	if got != "ready" {
+		t.Errorf("got %q, want %q", got, "ready")
+	}
+	if calls != 4 {
+		t.Errorf("calls = %d, want 4", calls)
+	}
+}
+
+func TestDo_GivesUpAfterTheAttemptBudgetAndReportsTheLastError(t *testing.T) {
+	// A genuinely broken issuer must still fail — retrying forever would turn
+	// a config error into a silent hang, which is worse than crash-looping.
+	last := errors.New("oidc discovery: status 404")
+	calls := 0
+
+	_, err := Do(context.Background(), fastPolicy(3), func(context.Context) (string, error) {
+		calls++
+		return "", last
+	})
+
+	if !errors.Is(err, last) {
+		t.Fatalf("err = %v, want it to wrap the last failure", err)
+	}
+	if calls != 3 {
+		t.Errorf("calls = %d, want 3 (the attempt budget)", calls)
+	}
+}
+
+func TestDo_StopsPromptlyWhenTheContextIsCancelled(t *testing.T) {
+	ctx, cancel := context.WithCancel(context.Background())
+	calls := 0
+
+	done := make(chan struct{})
+	var err error
+	go func() {
+		defer close(done)
+		_, err = Do(ctx, Policy{Attempts: 100, Base: 50 * time.Millisecond, Max: time.Second},
+			func(context.Context) (string, error) {
+				calls++
+				if calls == 1 {
+					cancel()
+				}
+				return "", errors.New("still down")
+			})
+	}()
+
+	select {
+	case <-done:
+	case <-time.After(2 * time.Second):
+		t.Fatal("Do did not return after context cancellation")
+	}
+	if !errors.Is(err, context.Canceled) {
+		t.Errorf("err = %v, want context.Canceled", err)
+	}
+}
+
+func TestDo_BacksOffAndIsCappedByMax(t *testing.T) {
+	var delays []time.Duration
+	p := Policy{Attempts: 5, Base: 10 * time.Millisecond, Max: 25 * time.Millisecond}
+
+	last := time.Now()
+	_, _ = Do(context.Background(), p, func(context.Context) (string, error) {
+		now := time.Now()
+		delays = append(delays, now.Sub(last))
+		last = now
+		return "", errors.New("down")
+	})
+
+	// delays[0] is the first call (no wait); the rest are the sleeps.
+	if len(delays) != 5 {
+		t.Fatalf("attempts = %d, want 5", len(delays))
+	}
+	if delays[1] >= delays[2] {
+		t.Errorf("backoff is not growing: %v then %v", delays[1], delays[2])
+	}
+	for i, d := range delays[1:] {
+		if d > 2*p.Max {
+			t.Errorf("delay %d = %v, exceeds the Max cap %v with slack", i+1, d, p.Max)
+		}
+	}
+}
+
+func TestPolicy_ZeroValueStillMakesOneAttempt(t *testing.T) {
+	// A caller that forgets to configure the policy must not silently get a
+	// no-op that returns a nil validator and a nil error.
+	calls := 0
+	_, err := Do(context.Background(), Policy{}, func(context.Context) (string, error) {
+		calls++
+		return "", errors.New("down")
+	})
+
+	if calls != 1 {
+		t.Errorf("calls = %d, want 1", calls)
+	}
+	if err == nil {
+		t.Error("err = nil, want the failure surfaced")
+	}
+}