diff --git a/nomad/eval_broker.go b/nomad/eval_broker.go
index 783ad84f0..3733a2884 100644
--- a/nomad/eval_broker.go
+++ b/nomad/eval_broker.go
@@ -28,6 +28,14 @@ var (
 
 	// ErrNackTimeoutReached is returned if an expired evaluation is reset
 	ErrNackTimeoutReached = errors.New("evaluation nack timeout reached")
+
+	// initialNackReenqueueDelay is the delay applied before re-enqueuing a
+	// Nacked evaluation for the first time
+	initialNackReenqueueDelay = time.Second
+
+	// subsequentNackReenqueueDelay is a compounding delay applied on each
+	// subsequent Nack for an evaluation.
+	subsequentNackReenqueueDelay = 20 * time.Second
 )
 
 // EvalBroker is used to manage brokering of evaluations. When an evaluation is
@@ -76,6 +84,10 @@ type EvalBroker struct {
 	// timeWait has evaluations that are waiting for time to elapse
 	timeWait map[string]*time.Timer
 
+	// Nack delays are defaulted and are only made available for testing
+	initialNackDelay    time.Duration
+	subsequentNackDelay time.Duration
+
 	l sync.RWMutex
 }
 
@@ -100,18 +112,20 @@ func NewEvalBroker(timeout time.Duration, deliveryLimit int) (*EvalBroker, error
 		return nil, fmt.Errorf("timeout cannot be negative")
 	}
 	b := &EvalBroker{
-		nackTimeout:   timeout,
-		deliveryLimit: deliveryLimit,
-		enabled:       false,
-		stats:         new(BrokerStats),
-		evals:         make(map[string]int),
-		jobEvals:      make(map[string]string),
-		blocked:       make(map[string]PendingEvaluations),
-		ready:         make(map[string]PendingEvaluations),
-		unack:         make(map[string]*unackEval),
-		waiting:       make(map[string]chan struct{}),
-		requeue:       make(map[string]*structs.Evaluation),
-		timeWait:      make(map[string]*time.Timer),
+		nackTimeout:         timeout,
+		deliveryLimit:       deliveryLimit,
+		enabled:             false,
+		stats:               new(BrokerStats),
+		evals:               make(map[string]int),
+		jobEvals:            make(map[string]string),
+		blocked:             make(map[string]PendingEvaluations),
+		ready:               make(map[string]PendingEvaluations),
+		unack:               make(map[string]*unackEval),
+		waiting:             make(map[string]chan struct{}),
+		requeue:             make(map[string]*structs.Evaluation),
+		timeWait:            make(map[string]*time.Timer),
+		initialNackDelay:    initialNackReenqueueDelay,
+		subsequentNackDelay: subsequentNackReenqueueDelay,
 	}
 	b.stats.ByScheduler = make(map[string]*SchedulerStats)
 	return b, nil
@@ -187,17 +201,23 @@ func (b *EvalBroker) processEnqueue(eval *structs.Evaluation, token string) {
 
 	// Check if we need to enforce a wait
 	if eval.Wait > 0 {
-		timer := time.AfterFunc(eval.Wait, func() {
-			b.enqueueWaiting(eval)
-		})
-		b.timeWait[eval.ID] = timer
-		b.stats.TotalWaiting += 1
+		b.processWaitingEnqueue(eval)
 		return
 	}
 
 	b.enqueueLocked(eval, eval.Type)
 }
 
+// processWaitingEnqueue waits the given duration on the evaluation before
+// enqueueing.
+func (b *EvalBroker) processWaitingEnqueue(eval *structs.Evaluation) {
+	timer := time.AfterFunc(eval.Wait, func() {
+		b.enqueueWaiting(eval)
+	})
+	b.timeWait[eval.ID] = timer
+	b.stats.TotalWaiting += 1
+}
+
 // enqueueWaiting is used to enqueue a waiting evaluation
 func (b *EvalBroker) enqueueWaiting(eval *structs.Evaluation) {
 	b.l.Lock()
@@ -547,14 +567,40 @@ func (b *EvalBroker) Nack(evalID, token string) error {
 
 	// Check if we've hit the delivery limit, and re-enqueue
 	// in the failedQueue
-	if b.evals[evalID] >= b.deliveryLimit {
+	if dequeues := b.evals[evalID]; dequeues >= b.deliveryLimit {
 		b.enqueueLocked(unack.Eval, failedQueue)
 	} else {
-		b.enqueueLocked(unack.Eval, unack.Eval.Type)
+		e := unack.Eval
+		e.Wait = b.nackReenqueueDelay(e, dequeues)
+
+		// See if there should be a delay before re-enqueuing
+		if e.Wait > 0 {
+			b.processWaitingEnqueue(e)
+		} else {
+			b.enqueueLocked(e, e.Type)
+		}
 	}
+
 	return nil
 }
 
+// nackReenqueueDelay is used to determine the delay that should be applied on
+// the evaluation given the number of previous attempts
+func (b *EvalBroker) nackReenqueueDelay(eval *structs.Evaluation, prevDequeues int) time.Duration {
+	var delay time.Duration
+
+	switch {
+	case prevDequeues <= 0:
+	case prevDequeues == 1:
+		delay = b.initialNackDelay
+	default:
+		// For each subsequent nack compound a delay
+		delay = time.Duration(prevDequeues-1) * b.subsequentNackDelay
+	}
+
+	return delay
+}
+
 // PauseNackTimeout is used to pause the Nack timeout for an eval that is making
 // progress but is in a potentially unbounded operation such as the plan queue.
 func (b *EvalBroker) PauseNackTimeout(evalID, token string) error {
diff --git a/nomad/eval_broker_test.go b/nomad/eval_broker_test.go
index ab6ecedf0..c263fb1ef 100644
--- a/nomad/eval_broker_test.go
+++ b/nomad/eval_broker_test.go
@@ -1,11 +1,13 @@
 package nomad
 
 import (
+	"fmt"
 	"testing"
 	"time"
 
 	"github.com/hashicorp/nomad/nomad/mock"
 	"github.com/hashicorp/nomad/nomad/structs"
+	"github.com/hashicorp/nomad/testutil"
 )
 
 var (
@@ -23,6 +25,11 @@ func testBroker(t *testing.T, timeout time.Duration) *EvalBroker {
 	if err != nil {
 		t.Fatalf("err: %v", err)
 	}
+
+	// Tune the Nack delay
+	b.initialNackDelay = 5 * time.Millisecond
+	b.subsequentNackDelay = 50 * time.Millisecond
+
 	return b
 }
 
@@ -126,19 +133,28 @@ func TestEvalBroker_Enqueue_Dequeue_Nack_Ack(t *testing.T) {
 	}
 
 	// Check the stats
-	stats = b.Stats()
-	if stats.TotalReady != 1 {
-		t.Fatalf("bad: %#v", stats)
-	}
-	if stats.TotalUnacked != 0 {
-		t.Fatalf("bad: %#v", stats)
-	}
-	if stats.ByScheduler[eval.Type].Ready != 1 {
-		t.Fatalf("bad: %#v", stats)
-	}
-	if stats.ByScheduler[eval.Type].Unacked != 0 {
-		t.Fatalf("bad: %#v", stats)
-	}
+	testutil.WaitForResult(func() (bool, error) {
+		stats = b.Stats()
+		if stats.TotalReady != 1 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.TotalUnacked != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.TotalWaiting != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.ByScheduler[eval.Type].Ready != 1 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.ByScheduler[eval.Type].Unacked != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+
+		return true, nil
+	}, func(e error) {
+		t.Fatal(e)
+	})
 
 	// Dequeue should work again
 	out2, token2, err := b.Dequeue(defaultSched, time.Second)
@@ -192,6 +208,163 @@ func TestEvalBroker_Enqueue_Dequeue_Nack_Ack(t *testing.T) {
 	}
 }
 
+func TestEvalBroker_Nack_Delay(t *testing.T) {
+	b := testBroker(t, 0)
+
+	// Enqueue, but broker is disabled!
+	b.SetEnabled(true)
+	eval := mock.Eval()
+	b.Enqueue(eval)
+
+	// Dequeue should work
+	out, token, err := b.Dequeue(defaultSched, time.Second)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+	if out != eval {
+		t.Fatalf("bad : %#v", out)
+	}
+
+	// Nack back into the queue
+	err = b.Nack(eval.ID, token)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+
+	if _, ok := b.Outstanding(out.ID); ok {
+		t.Fatalf("should not be outstanding")
+	}
+
+	// Check the stats to ensure that it is waiting
+	stats := b.Stats()
+	if stats.TotalReady != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+	if stats.TotalUnacked != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+	if stats.TotalWaiting != 1 {
+		t.Fatalf("bad: %#v", stats)
+	}
+	if stats.ByScheduler[eval.Type].Ready != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+	if stats.ByScheduler[eval.Type].Unacked != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+
+	// Now wait for it to be re-enqueued
+	testutil.WaitForResult(func() (bool, error) {
+		stats = b.Stats()
+		if stats.TotalReady != 1 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.TotalUnacked != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.TotalWaiting != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.ByScheduler[eval.Type].Ready != 1 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.ByScheduler[eval.Type].Unacked != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+
+		return true, nil
+	}, func(e error) {
+		t.Fatal(e)
+	})
+
+	// Dequeue should work again
+	out2, token2, err := b.Dequeue(defaultSched, time.Second)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+	if out2 != eval {
+		t.Fatalf("bad : %#v", out2)
+	}
+	if token2 == token {
+		t.Fatalf("should get a new token")
+	}
+
+	// Capture the time
+	start := time.Now()
+
+	// Nack back into the queue
+	err = b.Nack(eval.ID, token2)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+
+	// Now wait for it to be re-enqueued
+	testutil.WaitForResult(func() (bool, error) {
+		stats = b.Stats()
+		if stats.TotalReady != 1 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.TotalUnacked != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.TotalWaiting != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.ByScheduler[eval.Type].Ready != 1 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.ByScheduler[eval.Type].Unacked != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+
+		return true, nil
+	}, func(e error) {
+		t.Fatal(e)
+	})
+
+	delay := time.Now().Sub(start)
+	if delay < b.subsequentNackDelay {
+		t.Fatalf("bad: delay was %v; want at least %v", delay, b.subsequentNackDelay)
+	}
+
+	// Dequeue should work again
+	out3, token3, err := b.Dequeue(defaultSched, time.Second)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+	if out3 != eval {
+		t.Fatalf("bad : %#v", out3)
+	}
+	if token3 == token || token3 == token2 {
+		t.Fatalf("should get a new token")
+	}
+
+	// Ack finally
+	err = b.Ack(eval.ID, token3)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+
+	if _, ok := b.Outstanding(out.ID); ok {
+		t.Fatalf("should not be outstanding")
+	}
+
+	// Check the stats
+	stats = b.Stats()
+	if stats.TotalReady != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+	if stats.TotalUnacked != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+	if stats.ByScheduler[eval.Type].Ready != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+	if stats.ByScheduler[eval.Type].Unacked != 0 {
+		t.Fatalf("bad: %#v", stats)
+	}
+}
+
 func TestEvalBroker_Serialize_DuplicateJobID(t *testing.T) {
 	b := testBroker(t, 0)
 	b.SetEnabled(true)
@@ -472,7 +645,7 @@ func TestEvalBroker_Dequeue_FIFO(t *testing.T) {
 func TestEvalBroker_Dequeue_Fairness(t *testing.T) {
 	b := testBroker(t, 0)
 	b.SetEnabled(true)
-	NUM := 100
+	NUM := 1000
 
 	for i := 0; i < NUM; i++ {
 		eval1 := mock.Eval()
@@ -503,7 +676,7 @@ func TestEvalBroker_Dequeue_Fairness(t *testing.T) {
 
 		// This will fail randomly at times. It is very hard to
 		// test deterministically that its acting randomly.
-		if counter >= 25 || counter <= -25 {
+		if counter >= 250 || counter <= -250 {
 			t.Fatalf("unlikely sequence: %d", counter)
 		}
 	}
@@ -584,7 +757,7 @@ func TestEvalBroker_Nack_Timeout(t *testing.T) {
 
 // Ensure we nack in a timely manner
 func TestEvalBroker_Nack_TimeoutReset(t *testing.T) {
-	b := testBroker(t, 5*time.Millisecond)
+	b := testBroker(t, 50*time.Millisecond)
 	b.SetEnabled(true)
 
 	// Enqueue
@@ -601,8 +774,8 @@ func TestEvalBroker_Nack_TimeoutReset(t *testing.T) {
 		t.Fatalf("bad: %v", out)
 	}
 
-	// Reset in 2 milliseconds
-	time.Sleep(2 * time.Millisecond)
+	// Reset in 20 milliseconds
+	time.Sleep(20 * time.Millisecond)
 	if err := b.OutstandingReset(out.ID, token); err != nil {
 		t.Fatalf("err: %v", err)
 	}
@@ -618,13 +791,13 @@ func TestEvalBroker_Nack_TimeoutReset(t *testing.T) {
 	}
 
 	// Check the nack timer
-	if diff := end.Sub(start); diff < 7*time.Millisecond {
+	if diff := end.Sub(start); diff < 75*time.Millisecond {
 		t.Fatalf("bad: %#v", diff)
 	}
 }
 
 func TestEvalBroker_PauseResumeNackTimeout(t *testing.T) {
-	b := testBroker(t, 5*time.Millisecond)
+	b := testBroker(t, 50*time.Millisecond)
 	b.SetEnabled(true)
 
 	// Enqueue
@@ -641,14 +814,14 @@ func TestEvalBroker_PauseResumeNackTimeout(t *testing.T) {
 		t.Fatalf("bad: %v", out)
 	}
 
-	// Pause in 2 milliseconds
-	time.Sleep(2 * time.Millisecond)
+	// Pause in 20 milliseconds
+	time.Sleep(20 * time.Millisecond)
 	if err := b.PauseNackTimeout(out.ID, token); err != nil {
 		t.Fatalf("err: %v", err)
 	}
 
 	go func() {
-		time.Sleep(2 * time.Millisecond)
+		time.Sleep(20 * time.Millisecond)
 		if err := b.ResumeNackTimeout(out.ID, token); err != nil {
 			t.Fatalf("err: %v", err)
 		}
@@ -665,7 +838,7 @@ func TestEvalBroker_PauseResumeNackTimeout(t *testing.T) {
 	}
 
 	// Check the nack timer
-	if diff := end.Sub(start); diff < 9*time.Millisecond {
+	if diff := end.Sub(start); diff < 95*time.Millisecond {
 		t.Fatalf("bad: %#v", diff)
 	}
 }
@@ -820,7 +993,7 @@ func TestEvalBroker_Wait(t *testing.T) {
 	}
 
 	// Let the wait elapse
-	time.Sleep(15 * time.Millisecond)
+	time.Sleep(20 * time.Millisecond)
 
 	// Verify ready
 	stats = b.Stats()
@@ -976,14 +1149,20 @@ func TestEvalBroker_EnqueueAll_Requeue_Nack(t *testing.T) {
 	}
 
 	// Check stats again as this should cause the re-enqueued one to be dropped
-	stats = b.Stats()
-	if stats.TotalReady != 1 {
-		t.Fatalf("bad: %#v", stats)
-	}
-	if stats.TotalUnacked != 0 {
-		t.Fatalf("bad: %#v", stats)
-	}
-	if len(b.requeue) != 0 {
-		t.Fatalf("bad: %#v", b.requeue)
-	}
+	testutil.WaitForResult(func() (bool, error) {
+		stats = b.Stats()
+		if stats.TotalReady != 1 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if stats.TotalUnacked != 0 {
+			return false, fmt.Errorf("bad: %#v", stats)
+		}
+		if len(b.requeue) != 0 {
+			return false, fmt.Errorf("bad: %#v", b.requeue)
+		}
+
+		return true, nil
+	}, func(e error) {
+		t.Fatal(e)
+	})
 }