diff --git a/authorize/authorize.go b/authorize/authorize.go
index 959056970..e3be78eda 100644
--- a/authorize/authorize.go
+++ b/authorize/authorize.go
@@ -24,8 +24,10 @@ import (
 	"github.com/pomerium/pomerium/pkg/contextutil"
 	"github.com/pomerium/pomerium/pkg/cryptutil"
 	"github.com/pomerium/pomerium/pkg/grpc/databroker"
+	"github.com/pomerium/pomerium/pkg/grpc/session"
 	"github.com/pomerium/pomerium/pkg/grpc/user"
 	"github.com/pomerium/pomerium/pkg/policy/criteria"
+	"github.com/pomerium/pomerium/pkg/protoutil"
 	"github.com/pomerium/pomerium/pkg/storage"
 	"github.com/pomerium/pomerium/pkg/telemetry/requestid"
 	"github.com/pomerium/pomerium/pkg/telemetry/trace"
@@ -33,11 +35,12 @@ import (
 
 // Authorize struct holds
 type Authorize struct {
-	state             *atomicutil.Value[*authorizeState]
-	store             *store.Store
-	currentConfig     *atomicutil.Value[*config.Config]
-	accessTracker     *AccessTracker
-	groupsCacheWarmer *cacheWarmer
+	state               *atomicutil.Value[*authorizeState]
+	store               *store.Store
+	currentConfig       *atomicutil.Value[*config.Config]
+	accessTracker       *AccessTracker
+	groupsCacheWarmer   *cacheWarmer
+	sessionsCacheWarmer *cacheWarmer
 
 	tracerProvider oteltrace.TracerProvider
 	tracer         oteltrace.Tracer
@@ -67,6 +70,7 @@ func New(ctx context.Context, cfg *config.Config) (*Authorize, error) {
 	a.state = atomicutil.NewValue(state)
 
 	a.groupsCacheWarmer = newCacheWarmer(state.dataBrokerClientConnection, storage.GlobalCache, directory.GroupRecordType)
+	a.sessionsCacheWarmer = newCacheWarmer(state.dataBrokerClientConnection, storage.GlobalCache, protoutil.GetTypeURL(&session.Session{}))
 	return a, nil
 }
 
@@ -86,6 +90,10 @@ func (a *Authorize) Run(ctx context.Context) error {
 		a.groupsCacheWarmer.Run(ctx)
 		return nil
 	})
+	eg.Go(func() error {
+		a.sessionsCacheWarmer.Run(ctx)
+		return nil
+	})
 	return eg.Wait()
 }
 
@@ -173,6 +181,7 @@ func (a *Authorize) OnConfigChange(ctx context.Context, cfg *config.Config) {
 
 		if currentState.dataBrokerClientConnection != newState.dataBrokerClientConnection {
 			a.groupsCacheWarmer.UpdateConn(newState.dataBrokerClientConnection)
+			a.sessionsCacheWarmer.UpdateConn(newState.dataBrokerClientConnection)
 		}
 	}
 }
diff --git a/authorize/cache_warmer.go b/authorize/cache_warmer.go
index 41c1d0ae2..7564b9db8 100644
--- a/authorize/cache_warmer.go
+++ b/authorize/cache_warmer.go
@@ -111,6 +111,11 @@ func (h cacheWarmerSyncerHandler) UpdateRecords(ctx context.Context, serverVersi
 			log.Ctx(ctx).Error().Err(err).Msg("cache-warmer: failed to marshal query request")
 			continue
 		}
+		if record.DeletedAt != nil {
+			log.Ctx(ctx).Info().Msg("record deleted: " + record.Id)
+			h.cache.Invalidate(key)
+			return
+		}
 		value, err := storage.MarshalQueryResponse(res)
 		if err != nil {
 			log.Ctx(ctx).Error().Err(err).Msg("cache-warmer: failed to marshal query response")
diff --git a/authorize/ssh_grpc.go b/authorize/ssh_grpc.go
index b2f7940e8..eb418ac6e 100644
--- a/authorize/ssh_grpc.go
+++ b/authorize/ssh_grpc.go
@@ -29,7 +29,9 @@ import (
 	"github.com/pomerium/pomerium/config"
 	"github.com/pomerium/pomerium/internal/log"
 	"github.com/pomerium/pomerium/internal/sessions"
+	"github.com/pomerium/pomerium/pkg/grpc/databroker"
 	"github.com/pomerium/pomerium/pkg/grpc/session"
+	"github.com/pomerium/pomerium/pkg/grpcutil"
 	"github.com/pomerium/pomerium/pkg/identity"
 	"github.com/pomerium/pomerium/pkg/identity/manager"
 	"github.com/pomerium/pomerium/pkg/identity/oauth"
@@ -278,7 +280,7 @@ func (a *Authorize) ManageStream(
 						sendC <- handleEvaluatorResponseForSSH(res, state)
 
 						if res.Allow.Value && !res.Deny.Value {
-							a.startContinuousAuthorization(ctx, errC, req, session.Id)
+							a.startContinuousAuthorization(ctx, errC, req, session)
 						}
 					}
 
@@ -411,7 +413,7 @@ func (a *Authorize) ManageStream(
 					sendC <- handleEvaluatorResponseForSSH(res, state)
 
 					if res.Allow.Value && !res.Deny.Value {
-						a.startContinuousAuthorization(ctx, errC, req, state.Session.Id)
+						a.startContinuousAuthorization(ctx, errC, req, state.Session)
 					}
 				} else {
 					resp := extensions_ssh.ServerMessage{
@@ -658,20 +660,35 @@ func (a *Authorize) startContinuousAuthorization(
 	ctx context.Context,
 	errC chan<- error,
 	req *evaluator.Request,
-	sessionID string,
+	session *session.Session,
 ) {
 	recheck := func() {
 		// XXX: probably want to log the results of this evaluation only if it changes
-		res, _ := a.evaluate(ctx, req, &sessions.State{ID: sessionID})
+		res, _ := a.evaluate(ctx, req, &sessions.State{ID: session.Id})
 		if !res.Allow.Value || res.Deny.Value {
 			errC <- fmt.Errorf("no longer authorized")
 		}
 	}
 
-	ticker := time.NewTicker(time.Second)
+	keyReq := &databroker.QueryRequest{
+		Type:  grpcutil.GetTypeURL(session),
+		Limit: 1,
+	}
+	keyReq.SetFilterByIDOrIndex(session.Id)
+	key, err := (&proto.MarshalOptions{
+		Deterministic: true,
+	}).Marshal(keyReq)
+	if err != nil {
+		panic(err)
+	}
+
+	ticker := time.NewTicker(10 * time.Second)
 	go func() {
 		for {
 			select {
+			case <-a.sessionsCacheWarmer.cache.Wait(key):
+				errC <- fmt.Errorf("session expired")
+				return
 			case <-ticker.C:
 				recheck()
 			case <-ctx.Done():
@@ -1177,6 +1194,9 @@ func (a *Authorize) NewPortalCommand(
 			if err != nil {
 				return err
 			}
+			if answer.(model).choice == "" {
+				return nil // quit/ctrl+c
+			}
 			var handOff *anypb.Any
 			if strings.HasPrefix(answer.(model).choice, "[demo] mirror session: ") {
 				id, err := strconv.ParseUint(strings.TrimPrefix(answer.(model).choice, "[demo] mirror session: "), 10, 64)
@@ -1216,7 +1236,7 @@ func (a *Authorize) NewPortalCommand(
 				}
 
 				if res.Allow.Value && !res.Deny.Value {
-					a.startContinuousAuthorization(state.Context, state.ErrorC, req, state.Session.Id)
+					a.startContinuousAuthorization(state.Context, state.ErrorC, req, state.Session)
 				} else {
 					return fmt.Errorf("not authorized")
 				}
diff --git a/config/envoyconfig/listeners_ssh.go b/config/envoyconfig/listeners_ssh.go
index fbb779e09..bdfcb9b5a 100644
--- a/config/envoyconfig/listeners_ssh.go
+++ b/config/envoyconfig/listeners_ssh.go
@@ -176,6 +176,7 @@ func (b *Builder) buildRouteConfig(_ context.Context, cfg *config.Config) (*envo
 							ClusterSpecifier: &envoy_generic_proxy_action_v3.RouteAction_Cluster{
 								Cluster: clusterId,
 							},
+							Timeout: durationpb.New(0),
 						}),
 					},
 				},
diff --git a/go.mod b/go.mod
index 306f2dd22..10649981c 100644
--- a/go.mod
+++ b/go.mod
@@ -254,7 +254,7 @@ require (
 	go.uber.org/multierr v1.11.0 // indirect
 	go.uber.org/zap/exp v0.3.0 // indirect
 	golang.org/x/exp v0.0.0-20240808152545-0cdaa3abc0fa // indirect
-	golang.org/x/mod v0.20.0 // indirect
+	golang.org/x/mod v0.21.0 // indirect
 	golang.org/x/text v0.23.0 // indirect
 	golang.org/x/tools v0.24.0 // indirect
 	google.golang.org/genproto v0.0.0-20241118233622-e639e219e697 // indirect
diff --git a/go.sum b/go.sum
index 5578f0b3c..1c0d417eb 100644
--- a/go.sum
+++ b/go.sum
@@ -817,8 +817,8 @@ golang.org/x/mod v0.2.0/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
 golang.org/x/mod v0.3.0/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
 golang.org/x/mod v0.6.0-dev.0.20220419223038-86c51ed26bb4/go.mod h1:jJ57K6gSWd91VN4djpZkiMVwK6gcyfeH4XE8wZrZaV4=
 golang.org/x/mod v0.8.0/go.mod h1:iBbtSCu2XBx23ZKBPSOrRkjjQPZFPuis4dIYUhu/chs=
-golang.org/x/mod v0.20.0 h1:utOm6MM3R3dnawAiJgn0y+xvuYRsm1RKM/4giyfDgV0=
-golang.org/x/mod v0.20.0/go.mod h1:hTbmBsO62+eylJbnUtE2MGJUyE7QWk4xUqPFrRgJ+7c=
+golang.org/x/mod v0.21.0 h1:vvrHzRwRfVKSiLrG+d4FMl/Qi4ukBCE6kZlTUkDYRT0=
+golang.org/x/mod v0.21.0/go.mod h1:6SkKJ3Xj0I0BrPOZoBy3bdMptDDU9oJrpohJ3eWZ1fY=
 golang.org/x/net v0.0.0-20180724234803-3673e40ba225/go.mod h1:mL1N/T3taQHkDXs73rZJwtUhF3w3ftmwwsq0BUmARs4=
 golang.org/x/net v0.0.0-20180826012351-8a410e7b638d/go.mod h1:mL1N/T3taQHkDXs73rZJwtUhF3w3ftmwwsq0BUmARs4=
 golang.org/x/net v0.0.0-20180906233101-161cd47e91fd/go.mod h1:mL1N/T3taQHkDXs73rZJwtUhF3w3ftmwwsq0BUmARs4=
diff --git a/pkg/storage/cache.go b/pkg/storage/cache.go
index 3d8d563e6..f864486b9 100644
--- a/pkg/storage/cache.go
+++ b/pkg/storage/cache.go
@@ -5,6 +5,7 @@ import (
 	"encoding/binary"
 	"sync"
 	"time"
+	"unique"
 
 	"github.com/VictoriaMetrics/fastcache"
 	"golang.org/x/sync/singleflight"
@@ -20,6 +21,7 @@ type Cache interface {
 	Invalidate(key []byte)
 	InvalidateAll()
 	Set(expiry time.Time, key, value []byte)
+	Wait(key []byte) <-chan struct{}
 }
 
 type globalCache struct {
@@ -28,6 +30,7 @@ type globalCache struct {
 	singleflight singleflight.Group
 	mu           sync.RWMutex
 	fastcache    *fastcache.Cache
+	waiters      map[unique.Handle[string]]chan struct{}
 }
 
 // NewGlobalCache creates a new Cache backed by fastcache and a TTL.
@@ -35,6 +38,7 @@ func NewGlobalCache(ttl time.Duration) Cache {
 	return &globalCache{
 		ttl:       ttl,
 		fastcache: fastcache.New(256 * 1024 * 1024), // up to 256MB of RAM
+		waiters:   map[unique.Handle[string]]chan struct{}{},
 	}
 }
 
@@ -71,12 +75,40 @@ func (cache *globalCache) GetOrUpdate(
 func (cache *globalCache) Invalidate(key []byte) {
 	cache.mu.Lock()
 	cache.fastcache.Del(key)
+	keyHandle := unique.Make(string(key))
+	if c, ok := cache.waiters[keyHandle]; ok {
+		close(c)
+		delete(cache.waiters, keyHandle)
+	}
 	cache.mu.Unlock()
 }
 
+var expiredC = make(chan struct{})
+
+func init() {
+	close(expiredC)
+}
+
+func (cache *globalCache) Wait(key []byte) <-chan struct{} {
+	cache.mu.Lock()
+	defer cache.mu.Unlock()
+	if !cache.fastcache.Has(key) {
+		return expiredC
+	}
+	keyHandle := unique.Make(string(key))
+	if _, ok := cache.waiters[keyHandle]; !ok {
+		cache.waiters[keyHandle] = make(chan struct{})
+	}
+	return cache.waiters[keyHandle]
+}
+
 func (cache *globalCache) InvalidateAll() {
 	cache.mu.Lock()
 	cache.fastcache.Reset()
+	for _, c := range cache.waiters {
+		close(c)
+	}
+	clear(cache.waiters)
 	cache.mu.Unlock()
 }