diff --git a/.changelog/19560.txt b/.changelog/19560.txt
new file mode 100644
index 00000000000..03a48506b96
--- /dev/null
+++ b/.changelog/19560.txt
@@ -0,0 +1,3 @@
+```release-note:bug
+server: Fix server not waiting for workers to submit nacks for dequeued evaluations before shutting down
+```
diff --git a/client/client.go b/client/client.go
index 18f5532a568..ec1004df706 100644
--- a/client/client.go
+++ b/client/client.go
@@ -48,6 +48,7 @@ import (
 	"github.com/hashicorp/nomad/command/agent/consul"
 	"github.com/hashicorp/nomad/helper"
 	"github.com/hashicorp/nomad/helper/envoy"
+	"github.com/hashicorp/nomad/helper/group"
 	"github.com/hashicorp/nomad/helper/pointer"
 	"github.com/hashicorp/nomad/helper/pool"
 	hstats "github.com/hashicorp/nomad/helper/stats"
@@ -255,7 +256,7 @@ type Client struct {
 
 	// shutdownGroup are goroutines that exit when shutdownCh is closed.
 	// Shutdown() blocks on Wait() after closing shutdownCh.
-	shutdownGroup group
+	shutdownGroup group.Group
 
 	// tokensClient is Nomad Client's custom Consul client for requesting Consul
 	// Service Identity tokens through Nomad Server.
@@ -840,7 +841,7 @@ func (c *Client) Shutdown() error {
 	// Stop Garbage collector
 	c.garbageCollector.Stop()
 
-	arGroup := group{}
+	arGroup := group.Group{}
 	if c.GetConfig().DevMode {
 		// In DevMode destroy all the running allocations.
 		for _, ar := range c.getAllocRunners() {
@@ -3354,33 +3355,6 @@ func (c *Client) GetTaskEventHandler(allocID, taskName string) drivermanager.Eve
 	return nil
 }
 
-// group wraps a func() in a goroutine and provides a way to block until it
-// exits. Inspired by https://godoc.org/golang.org/x/sync/errgroup
-type group struct {
-	wg sync.WaitGroup
-}
-
-// Go starts f in a goroutine and must be called before Wait.
-func (g *group) Go(f func()) {
-	g.wg.Add(1)
-	go func() {
-		defer g.wg.Done()
-		f()
-	}()
-}
-
-func (g *group) AddCh(ch <-chan struct{}) {
-	g.Go(func() {
-		<-ch
-	})
-}
-
-// Wait for all goroutines to exit. Must be called after all calls to Go
-// complete.
-func (g *group) Wait() {
-	g.wg.Wait()
-}
-
 // pendingClientUpdates are the set of allocation updates that the client is
 // waiting to send
 type pendingClientUpdates struct {
diff --git a/helper/broker/notify.go b/helper/broker/notify.go
index da2fda4c0e0..7a3f400e696 100644
--- a/helper/broker/notify.go
+++ b/helper/broker/notify.go
@@ -4,6 +4,7 @@
 package broker
 
 import (
+	"context"
 	"time"
 
 	"github.com/hashicorp/nomad/helper"
@@ -21,15 +22,18 @@ type GenericNotifier struct {
 	// subscription membership mapping.
 	subscribeCh   chan chan interface{}
 	unsubscribeCh chan chan interface{}
+
+	ctx context.Context
 }
 
 // NewGenericNotifier returns a generic notifier which can be used by a process
 // to notify many subscribers when a specific update is triggered.
-func NewGenericNotifier() *GenericNotifier {
+func NewGenericNotifier(ctx context.Context) *GenericNotifier {
 	return &GenericNotifier{
 		publishCh:     make(chan interface{}, 1),
 		subscribeCh:   make(chan chan interface{}, 1),
 		unsubscribeCh: make(chan chan interface{}, 1),
+		ctx:           ctx,
 	}
 }
 
@@ -46,7 +50,7 @@ func (g *GenericNotifier) Notify(msg interface{}) {
 // Run is a long-lived process which handles updating subscribers as well as
 // ensuring any update is sent to them. The passed stopCh is used to coordinate
 // shutdown.
-func (g *GenericNotifier) Run(stopCh <-chan struct{}) {
+func (g *GenericNotifier) Run() {
 
 	// Store our subscribers inline with a map. This map can only be accessed
 	// via a single channel update at a time, meaning we can manage without
@@ -55,7 +59,7 @@ func (g *GenericNotifier) Run(stopCh <-chan struct{}) {
 
 	for {
 		select {
-		case <-stopCh:
+		case <-g.ctx.Done():
 			return
 		case msgCh := <-g.subscribeCh:
 			subscribers[msgCh] = struct{}{}
@@ -83,7 +87,11 @@ func (g *GenericNotifier) WaitForChange(timeout time.Duration) interface{} {
 	// Create a channel and subscribe to any update. This channel is buffered
 	// to ensure we do not block the main broker process.
 	updateCh := make(chan interface{}, 1)
-	g.subscribeCh <- updateCh
+	select {
+	case <-g.ctx.Done():
+		return "shutting down"
+	case g.subscribeCh <- updateCh:
+	}
 
 	// Create a timeout timer and use the helper to ensure this routine doesn't
 	// panic and making the stop call clear.
@@ -93,7 +101,10 @@ func (g *GenericNotifier) WaitForChange(timeout time.Duration) interface{} {
 	// subscriber once it has been notified of a change, or reached its wait
 	// timeout.
 	defer func() {
-		g.unsubscribeCh <- updateCh
+		select {
+		case <-g.ctx.Done():
+		case g.unsubscribeCh <- updateCh:
+		}
 		close(updateCh)
 		timeoutStop()
 	}()
@@ -101,6 +112,8 @@ func (g *GenericNotifier) WaitForChange(timeout time.Duration) interface{} {
 	// Enter the main loop which listens for an update or timeout and returns
 	// this information to the subscriber.
 	select {
+	case <-g.ctx.Done():
+		return "shutting down"
 	case <-timeoutTimer.C:
 		return "wait timed out after " + timeout.String()
 	case update := <-updateCh:
diff --git a/helper/broker/notify_test.go b/helper/broker/notify_test.go
index 4d80c8fa1be..69b55d8082a 100644
--- a/helper/broker/notify_test.go
+++ b/helper/broker/notify_test.go
@@ -4,6 +4,7 @@
 package broker
 
 import (
+	"context"
 	"sync"
 	"testing"
 	"time"
@@ -16,11 +17,11 @@ func TestGenericNotifier(t *testing.T) {
 	ci.Parallel(t)
 
 	// Create the new notifier.
-	stopChan := make(chan struct{})
-	defer close(stopChan)
+	ctx, cancelFn := context.WithCancel(context.Background())
+	defer cancelFn()
 
-	notifier := NewGenericNotifier()
-	go notifier.Run(stopChan)
+	notifier := NewGenericNotifier(ctx)
+	go notifier.Run()
 
 	// Ensure we have buffered channels.
 	require.Equal(t, 1, cap(notifier.publishCh))
diff --git a/helper/group/group.go b/helper/group/group.go
new file mode 100644
index 00000000000..8803aa31224
--- /dev/null
+++ b/helper/group/group.go
@@ -0,0 +1,50 @@
+// Copyright (c) HashiCorp, Inc.
+// SPDX-License-Identifier: MPL-2.0
+
+package group
+
+import (
+	"context"
+	"sync"
+)
+
+// group wraps a func() in a goroutine and provides a way to block until it
+// exits. Inspired by https://godoc.org/golang.org/x/sync/errgroup
+type Group struct {
+	wg sync.WaitGroup
+}
+
+// Go starts f in a goroutine and must be called before Wait.
+func (g *Group) Go(f func()) {
+	g.wg.Add(1)
+	go func() {
+		defer g.wg.Done()
+		f()
+	}()
+}
+
+func (g *Group) AddCh(ch <-chan struct{}) {
+	g.Go(func() {
+		<-ch
+	})
+}
+
+// Wait for all goroutines to exit. Must be called after all calls to Go
+// complete.
+func (g *Group) Wait() {
+	g.wg.Wait()
+}
+
+// Wait for all goroutines to exit, or for the context to finish.
+// Must be called after all calls to Go complete.
+func (g *Group) WaitWithContext(ctx context.Context) {
+	doneCh := make(chan struct{})
+	go func() {
+		defer close(doneCh)
+		g.Wait()
+	}()
+	select {
+	case <-doneCh:
+	case <-ctx.Done():
+	}
+}
diff --git a/helper/raftutil/fsm.go b/helper/raftutil/fsm.go
index 249f46b6cb5..f39016c8969 100644
--- a/helper/raftutil/fsm.go
+++ b/helper/raftutil/fsm.go
@@ -4,6 +4,7 @@
 package raftutil
 
 import (
+	"context"
 	"fmt"
 	"io"
 	"path/filepath"
@@ -79,7 +80,7 @@ func dummyFSM(logger hclog.Logger) (nomadFSM, error) {
 	// use dummy non-enabled FSM dependencies
 	periodicDispatch := nomad.NewPeriodicDispatch(logger, nil)
 	blockedEvals := nomad.NewBlockedEvals(nil, logger)
-	evalBroker, err := nomad.NewEvalBroker(1, 1, 1, 1)
+	evalBroker, err := nomad.NewEvalBroker(context.Background(), 1, 1, 1, 1)
 	if err != nil {
 		return nil, err
 	}
diff --git a/nomad/eval_broker.go b/nomad/eval_broker.go
index bee38f9cc9d..249d9a1e4a1 100644
--- a/nomad/eval_broker.go
+++ b/nomad/eval_broker.go
@@ -137,7 +137,7 @@ type PendingEvaluations []*structs.Evaluation
 // initialNackDelay is the delay before making a Nacked evaluation available
 // again for the first Nack and subsequentNackDelay is the compounding delay
 // after the first Nack.
-func NewEvalBroker(timeout, initialNackDelay, subsequentNackDelay time.Duration, deliveryLimit int) (*EvalBroker, error) {
+func NewEvalBroker(ctx context.Context, timeout, initialNackDelay, subsequentNackDelay time.Duration, deliveryLimit int) (*EvalBroker, error) {
 	if timeout < 0 {
 		return nil, fmt.Errorf("timeout cannot be negative")
 	}
@@ -145,7 +145,7 @@ func NewEvalBroker(timeout, initialNackDelay, subsequentNackDelay time.Duration,
 		nackTimeout:          timeout,
 		deliveryLimit:        deliveryLimit,
 		enabled:              false,
-		enabledNotifier:      broker.NewGenericNotifier(),
+		enabledNotifier:      broker.NewGenericNotifier(ctx),
 		stats:                new(BrokerStats),
 		evals:                make(map[string]int),
 		jobEvals:             make(map[structs.NamespacedID]string),
diff --git a/nomad/eval_broker_test.go b/nomad/eval_broker_test.go
index 53a0bd5815e..5245aa39220 100644
--- a/nomad/eval_broker_test.go
+++ b/nomad/eval_broker_test.go
@@ -5,6 +5,7 @@ package nomad
 
 import (
 	"container/heap"
+	"context"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -54,7 +55,7 @@ func testBroker(t *testing.T, timeout time.Duration) *EvalBroker {
 }
 
 func testBrokerFromConfig(t *testing.T, c *Config) *EvalBroker {
-	b, err := NewEvalBroker(c.EvalNackTimeout, c.EvalNackInitialReenqueueDelay, c.EvalNackSubsequentReenqueueDelay, 3)
+	b, err := NewEvalBroker(context.Background(), c.EvalNackTimeout, c.EvalNackInitialReenqueueDelay, c.EvalNackSubsequentReenqueueDelay, 3)
 	if err != nil {
 		t.Fatalf("err: %v", err)
 	}
diff --git a/nomad/server.go b/nomad/server.go
index 477a6bd40d8..bbc897426f9 100644
--- a/nomad/server.go
+++ b/nomad/server.go
@@ -35,6 +35,7 @@ import (
 	"github.com/hashicorp/nomad/command/agent/consul"
 	"github.com/hashicorp/nomad/helper"
 	"github.com/hashicorp/nomad/helper/codec"
+	"github.com/hashicorp/nomad/helper/group"
 	"github.com/hashicorp/nomad/helper/pool"
 	"github.com/hashicorp/nomad/helper/stats"
 	"github.com/hashicorp/nomad/helper/tlsutil"
@@ -83,6 +84,10 @@ const (
 	// to replicate to gracefully leave the cluster.
 	raftRemoveGracePeriod = 5 * time.Second
 
+	// workerShutdownGracePeriod is the maximum time we will wait for workers to stop
+	// gracefully when the server shuts down
+	workerShutdownGracePeriod = 5 * time.Second
+
 	// defaultConsulDiscoveryInterval is how often to poll Consul for new
 	// servers if there is no leader.
 	defaultConsulDiscoveryInterval time.Duration = 3 * time.Second
@@ -265,6 +270,10 @@ type Server struct {
 	// aclCache is used to maintain the parsed ACL objects
 	aclCache *structs.ACLCache[*acl.ACL]
 
+	// workerShutdownGroup tracks the running worker goroutines so that Shutdown()
+	// can wait on their completion
+	workerShutdownGroup group.Group
+
 	// oidcProviderCache maintains a cache of OIDC providers. This is useful as
 	// the provider performs background HTTP requests. When the Nomad server is
 	// shutting down, the oidcProviderCache.Shutdown() function must be called.
@@ -299,16 +308,6 @@ type Server struct {
 // configuration, potentially returning an error
 func NewServer(config *Config, consulCatalog consul.CatalogAPI, consulConfigEntries consul.ConfigAPI, consulACLs consul.ACLsAPI) (*Server, error) {
 
-	// Create an eval broker
-	evalBroker, err := NewEvalBroker(
-		config.EvalNackTimeout,
-		config.EvalNackInitialReenqueueDelay,
-		config.EvalNackSubsequentReenqueueDelay,
-		config.EvalDeliveryLimit)
-	if err != nil {
-		return nil, err
-	}
-
 	// Configure TLS
 	tlsConf, err := tlsutil.NewTLSConfiguration(config.TLSConfig, true, true)
 	if err != nil {
@@ -347,9 +346,7 @@ func NewServer(config *Config, consulCatalog consul.CatalogAPI, consulConfigEntr
 		reconcileCh:             make(chan serf.Member, 32),
 		readyForConsistentReads: &atomic.Bool{},
 		eventCh:                 make(chan serf.Event, 256),
-		evalBroker:              evalBroker,
 		reapCancelableEvalsCh:   make(chan struct{}),
-		blockedEvals:            NewBlockedEvals(evalBroker, logger),
 		rpcTLS:                  incomingTLS,
 		aclCache:                aclCache,
 		workersEventCh:          make(chan interface{}, 1),
@@ -358,6 +355,21 @@ func NewServer(config *Config, consulCatalog consul.CatalogAPI, consulConfigEntr
 	s.shutdownCtx, s.shutdownCancel = context.WithCancel(context.Background())
 	s.shutdownCh = s.shutdownCtx.Done()
 
+	// Create an eval broker
+	evalBroker, err := NewEvalBroker(
+		s.shutdownCtx,
+		config.EvalNackTimeout,
+		config.EvalNackInitialReenqueueDelay,
+		config.EvalNackSubsequentReenqueueDelay,
+		config.EvalDeliveryLimit)
+	if err != nil {
+		return nil, err
+	}
+	s.evalBroker = evalBroker
+
+	// Create the blocked evals
+	s.blockedEvals = NewBlockedEvals(s.evalBroker, s.logger)
+
 	// Create the RPC handler
 	s.rpcHandler = newRpcHandler(s)
 
@@ -456,7 +468,7 @@ func NewServer(config *Config, consulCatalog consul.CatalogAPI, consulConfigEntr
 
 	// Start the eval broker notification system so any subscribers can get
 	// updates when the processes SetEnabled is triggered.
-	go s.evalBroker.enabledNotifier.Run(s.shutdownCh)
+	go s.evalBroker.enabledNotifier.Run()
 
 	// Setup the node drainer.
 	s.setupNodeDrainer()
@@ -673,6 +685,13 @@ func (s *Server) Shutdown() error {
 	s.shutdown = true
 	s.shutdownCancel()
 
+	s.workerLock.Lock()
+	defer s.workerLock.Unlock()
+	s.stopOldWorkers(s.workers)
+	workerShutdownTimeoutCtx, cancelWorkerShutdownTimeoutCtx := context.WithTimeout(context.Background(), workerShutdownGracePeriod)
+	defer cancelWorkerShutdownTimeoutCtx()
+	s.workerShutdownGroup.WaitWithContext(workerShutdownTimeoutCtx)
+
 	if s.serf != nil {
 		s.serf.Shutdown()
 	}
@@ -1743,7 +1762,7 @@ func (s *Server) setupWorkersLocked(ctx context.Context, poolArgs SchedulerWorke
 			return err
 		} else {
 			s.logger.Debug("started scheduling worker", "id", w.ID(), "index", i+1, "of", s.config.NumSchedulers)
-
+			s.workerShutdownGroup.AddCh(w.ShutdownCh())
 			s.workers = append(s.workers, w)
 		}
 	}
diff --git a/nomad/worker.go b/nomad/worker.go
index ad66f454924..b49ebf4a2dc 100644
--- a/nomad/worker.go
+++ b/nomad/worker.go
@@ -98,6 +98,9 @@ type Worker struct {
 	workloadStatus SchedulerWorkerStatus
 	statusLock     sync.RWMutex
 
+	// shutdownCh is closed when the run function has exited
+	shutdownCh chan struct{}
+
 	pauseFlag bool
 	pauseLock sync.Mutex
 	pauseCond *sync.Cond
@@ -134,6 +137,7 @@ func newWorker(ctx context.Context, srv *Server, args SchedulerWorkerPoolArgs) *
 		srv:               srv,
 		start:             time.Now(),
 		status:            WorkerStarting,
+		shutdownCh:        make(chan struct{}),
 		enabledSchedulers: make([]string, len(args.EnabledSchedulers)),
 		failureBackoff:    time.Duration(0),
 	}
@@ -393,6 +397,7 @@ func (w *Worker) workerShuttingDown() bool {
 func (w *Worker) run(raftSyncLimit time.Duration) {
 	defer func() {
 		w.markStopped()
+		close(w.shutdownCh)
 	}()
 	w.setStatuses(WorkerStarted, WorkloadRunning)
 	w.logger.Debug("running")
@@ -894,3 +899,7 @@ func (w *Worker) backoffErr(base, limit time.Duration) bool {
 func (w *Worker) backoffReset() {
 	w.failures = 0
 }
+
+func (w *Worker) ShutdownCh() <-chan struct{} {
+	return w.shutdownCh
+}
diff --git a/nomad/worker_test.go b/nomad/worker_test.go
index a3c389b992c..777f694b147 100644
--- a/nomad/worker_test.go
+++ b/nomad/worker_test.go
@@ -57,20 +57,6 @@ func init() {
 	}
 }
 
-// NewTestWorker returns the worker without calling it's run method.
-func NewTestWorker(shutdownCtx context.Context, srv *Server) *Worker {
-	w := &Worker{
-		srv:               srv,
-		start:             time.Now(),
-		id:                uuid.Generate(),
-		enabledSchedulers: srv.config.EnabledSchedulers,
-	}
-	w.logger = srv.logger.ResetNamed("worker").With("worker_id", w.id)
-	w.pauseCond = sync.NewCond(&w.pauseLock)
-	w.ctx, w.cancelFn = context.WithCancel(shutdownCtx)
-	return w
-}
-
 func TestWorker_dequeueEvaluation(t *testing.T) {
 	ci.Parallel(t)
 
@@ -364,7 +350,8 @@ func TestWorker_runBackoff(t *testing.T) {
 	workerCtx, workerCancel := context.WithCancel(srv.shutdownCtx)
 	defer workerCancel()
 
-	w := NewTestWorker(workerCtx, srv)
+	poolArgs := getSchedulerWorkerPoolArgsFromConfigLocked(srv.config).Copy()
+	w := newWorker(workerCtx, srv, poolArgs)
 	doneCh := make(chan struct{})
 
 	go func() {