diff --git a/nomad/plan_apply.go b/nomad/plan_apply.go
index a3f7e7421..96b6edca9 100644
--- a/nomad/plan_apply.go
+++ b/nomad/plan_apply.go
@@ -126,13 +126,10 @@ func (s *Server) applyPlan(plan *structs.Plan, result *structs.PlanResult, snap
 	minUpdates := len(result.NodeUpdate)
 	minUpdates += len(result.NodeAllocation)
 
-	// Grab the job
-	job := plan.Job
-
 	// Setup the update request
 	req := structs.ApplyPlanResultsRequest{
 		AllocUpdateRequest: structs.AllocUpdateRequest{
-			Job:   job,
+			Job:   plan.Job,
 			Alloc: make([]*structs.Allocation, 0, minUpdates),
 		},
 		CreatedDeployment: plan.CreatedDeployment,
diff --git a/nomad/structs/structs.go b/nomad/structs/structs.go
index 13a2c5015..a595f9860 100644
--- a/nomad/structs/structs.go
+++ b/nomad/structs/structs.go
@@ -3710,6 +3710,11 @@ const (
 	DeploymentStatusSuccessful = "successful"
 	DeploymentStatusCancelled  = "cancelled"
 	DeploymentStatusPaused     = "paused"
+
+	// DeploymentStatusDescriptions are the various descriptions of the states a
+	// deployment can be in.
+	DeploymentStatusDescriptionStoppedJob = "Cancelled because job is stopped"
+	DeploymentStatusDescriptionNewerJob   = "Cancelled due to newer version of job"
 )
 
 // Deployment is the object that represents a job deployment which is used to
@@ -4591,9 +4596,23 @@ func (p *Plan) AppendAlloc(alloc *Allocation) {
 	p.NodeAllocation[node] = append(existing, alloc)
 }
 
+// AppendDeploymentUpdate attaches an deployment update to the plan for the
+// given deployment ID.
+func (p *Plan) AppendDeploymentUpdate(id, status, description string) {
+	update := &DeploymentStatusUpdate{
+		DeploymentID:      id,
+		Status:            status,
+		StatusDescription: description,
+	}
+	p.DeploymentUpdates = append(p.DeploymentUpdates, update)
+}
+
 // IsNoOp checks if this plan would do nothing
 func (p *Plan) IsNoOp() bool {
-	return len(p.NodeUpdate) == 0 && len(p.NodeAllocation) == 0
+	return len(p.NodeUpdate) == 0 &&
+		len(p.NodeAllocation) == 0 &&
+		p.CreatedDeployment == nil &&
+		len(p.DeploymentUpdates) == 0
 }
 
 // PlanResult is the result of a plan submitted to the leader.
diff --git a/scheduler/generic_sched.go b/scheduler/generic_sched.go
index 43f38f15e..a12cd1a8d 100644
--- a/scheduler/generic_sched.go
+++ b/scheduler/generic_sched.go
@@ -73,6 +73,8 @@ type GenericScheduler struct {
 	limitReached bool
 	nextEval     *structs.Evaluation
 
+	deployment *structs.Deployment
+
 	blocked        *structs.Evaluation
 	failedTGAllocs map[string]*structs.AllocMetric
 	queuedAllocs   map[string]int
@@ -187,11 +189,12 @@ func (s *GenericScheduler) process() (bool, error) {
 	ws := memdb.NewWatchSet()
 	s.job, err = s.state.JobByID(ws, s.eval.JobID)
 	if err != nil {
-		return false, fmt.Errorf("failed to get job '%s': %v",
-			s.eval.JobID, err)
+		return false, fmt.Errorf("failed to get job %q: %v", s.eval.JobID, err)
 	}
+
 	numTaskGroups := 0
-	if !s.job.Stopped() {
+	stopped := s.job.Stopped()
+	if !stopped {
 		numTaskGroups = len(s.job.TaskGroups)
 	}
 	s.queuedAllocs = make(map[string]int, numTaskGroups)
@@ -199,6 +202,30 @@ func (s *GenericScheduler) process() (bool, error) {
 	// Create a plan
 	s.plan = s.eval.MakePlan(s.job)
 
+	if !s.batch {
+		// Get any existing deployment
+		s.deployment, err = s.state.LatestDeploymentByJobID(ws, s.eval.JobID)
+		if err != nil {
+			return false, fmt.Errorf("failed to get job deployment %q: %v", s.eval.JobID, err)
+		}
+
+		// If there is an existing deployment, it should be cancelled under the
+		// following scenarios:
+		// 1) The current job is stopped.
+		// 2) The deployment is for an older version of the job.
+		if d := s.deployment; d != nil {
+			if stopped {
+				s.plan.AppendDeploymentUpdate(d.ID, structs.DeploymentStatusCancelled,
+					structs.DeploymentStatusDescriptionStoppedJob)
+				s.deployment = nil
+			} else if d.JobCreateIndex != s.job.CreateIndex || d.JobModifyIndex != s.job.JobModifyIndex {
+				s.plan.AppendDeploymentUpdate(d.ID, structs.DeploymentStatusCancelled,
+					structs.DeploymentStatusDescriptionNewerJob)
+				s.deployment = nil
+			}
+		}
+	}
+
 	// Reset the failed allocations
 	s.failedTGAllocs = nil
 
@@ -234,6 +261,7 @@ func (s *GenericScheduler) process() (bool, error) {
 		return true, nil
 	}
 
+	// XXX Don't need a next rolling update eval
 	// If the limit of placements was reached we need to create an evaluation
 	// to pickup from here after the stagger period.
 	if s.limitReached && s.nextEval == nil {
diff --git a/scheduler/generic_sched_test.go b/scheduler/generic_sched_test.go
index afb0e48d4..e1616b22e 100644
--- a/scheduler/generic_sched_test.go
+++ b/scheduler/generic_sched_test.go
@@ -2845,3 +2845,140 @@ func TestServiceSched_NodeDrain_Sticky(t *testing.T) {
 
 	h.AssertEvalStatus(t, structs.EvalStatusComplete)
 }
+
+// This test ensures that when a job is stopped, the scheduler properly cancels
+// an outstanding deployment.
+func TestServiceSched_CancelDeployment_Stopped(t *testing.T) {
+	h := NewHarness(t)
+
+	// Generate a fake job
+	job := mock.Job()
+	job.JobModifyIndex = job.CreateIndex + 1
+	job.ModifyIndex = job.CreateIndex + 1
+	job.Stop = true
+	noErr(t, h.State.UpsertJob(h.NextIndex(), job))
+
+	// Create a deployment
+	d := mock.Deployment()
+	d.JobID = job.ID
+	d.JobCreateIndex = job.CreateIndex
+	d.JobModifyIndex = job.JobModifyIndex - 1
+	noErr(t, h.State.UpsertDeployment(h.NextIndex(), d, false))
+
+	// Create a mock evaluation to deregister the job
+	eval := &structs.Evaluation{
+		ID:          structs.GenerateUUID(),
+		Priority:    50,
+		TriggeredBy: structs.EvalTriggerJobDeregister,
+		JobID:       job.ID,
+	}
+
+	// Process the evaluation
+	err := h.Process(NewServiceScheduler, eval)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+
+	// Ensure a single plan
+	if len(h.Plans) != 1 {
+		t.Fatalf("bad: %#v", h.Plans)
+	}
+	plan := h.Plans[0]
+
+	// Ensure the plan cancelled the existing deployment
+	ws := memdb.NewWatchSet()
+	out, err := h.State.LatestDeploymentByJobID(ws, job.ID)
+	noErr(t, err)
+
+	if out == nil {
+		t.Fatalf("No deployment for job")
+	}
+	if out.ID != d.ID {
+		t.Fatalf("Latest deployment for job is different than original deployment")
+	}
+	if out.Status != structs.DeploymentStatusCancelled {
+		t.Fatalf("Deployment status is %q, want %q", out.Status, structs.DeploymentStatusCancelled)
+	}
+	if out.StatusDescription != structs.DeploymentStatusDescriptionStoppedJob {
+		t.Fatalf("Deployment status description is %q, want %q",
+			out.StatusDescription, structs.DeploymentStatusDescriptionStoppedJob)
+	}
+
+	// Ensure the plan didn't allocate anything
+	var planned []*structs.Allocation
+	for _, allocList := range plan.NodeAllocation {
+		planned = append(planned, allocList...)
+	}
+	if len(planned) != 0 {
+		t.Fatalf("bad: %#v", plan)
+	}
+
+	h.AssertEvalStatus(t, structs.EvalStatusComplete)
+}
+
+// This test ensures that when a job is updated and had an old deployment, the scheduler properly cancels
+// the deployment.
+func TestServiceSched_CancelDeployment_NewerJob(t *testing.T) {
+	h := NewHarness(t)
+
+	// Generate a fake job
+	job := mock.Job()
+	noErr(t, h.State.UpsertJob(h.NextIndex(), job))
+
+	// Create a deployment for an old version of the job
+	d := mock.Deployment()
+	d.JobID = job.ID
+	noErr(t, h.State.UpsertDeployment(h.NextIndex(), d, false))
+
+	// Upsert again to bump job version
+	noErr(t, h.State.UpsertJob(h.NextIndex(), job))
+
+	// Create a mock evaluation to kick the job
+	eval := &structs.Evaluation{
+		ID:          structs.GenerateUUID(),
+		Priority:    50,
+		TriggeredBy: structs.EvalTriggerJobRegister,
+		JobID:       job.ID,
+	}
+
+	// Process the evaluation
+	err := h.Process(NewServiceScheduler, eval)
+	if err != nil {
+		t.Fatalf("err: %v", err)
+	}
+
+	// Ensure a single plan
+	if len(h.Plans) != 1 {
+		t.Fatalf("bad: %#v", h.Plans)
+	}
+	plan := h.Plans[0]
+
+	// Ensure the plan cancelled the existing deployment
+	ws := memdb.NewWatchSet()
+	out, err := h.State.LatestDeploymentByJobID(ws, job.ID)
+	noErr(t, err)
+
+	if out == nil {
+		t.Fatalf("No deployment for job")
+	}
+	if out.ID != d.ID {
+		t.Fatalf("Latest deployment for job is different than original deployment")
+	}
+	if out.Status != structs.DeploymentStatusCancelled {
+		t.Fatalf("Deployment status is %q, want %q", out.Status, structs.DeploymentStatusCancelled)
+	}
+	if out.StatusDescription != structs.DeploymentStatusDescriptionNewerJob {
+		t.Fatalf("Deployment status description is %q, want %q",
+			out.StatusDescription, structs.DeploymentStatusDescriptionNewerJob)
+	}
+	// Ensure the plan didn't allocate anything
+	var planned []*structs.Allocation
+	for _, allocList := range plan.NodeAllocation {
+		planned = append(planned, allocList...)
+	}
+	if len(planned) != 0 {
+		t.Fatalf("bad: %#v", plan)
+	}
+
+	h.AssertEvalStatus(t, structs.EvalStatusComplete)
+}
diff --git a/scheduler/scheduler.go b/scheduler/scheduler.go
index ddbf855c4..995b3affd 100644
--- a/scheduler/scheduler.go
+++ b/scheduler/scheduler.go
@@ -79,6 +79,10 @@ type State interface {
 
 	// GetJobByID is used to lookup a job by ID
 	JobByID(ws memdb.WatchSet, id string) (*structs.Job, error)
+
+	// LatestDeploymentByJobID returns the latest deployment matching the given
+	// job ID
+	LatestDeploymentByJobID(ws memdb.WatchSet, jobID string) (*structs.Deployment, error)
 }
 
 // Planner interface is used to submit a task allocation plan.
diff --git a/scheduler/testing.go b/scheduler/testing.go
index 74c01c486..af1411db1 100644
--- a/scheduler/testing.go
+++ b/scheduler/testing.go
@@ -6,6 +6,7 @@ import (
 	"os"
 	"sync"
 	"testing"
+	"time"
 
 	memdb "github.com/hashicorp/go-memdb"
 	"github.com/hashicorp/nomad/nomad/state"
@@ -108,19 +109,27 @@ func (h *Harness) SubmitPlan(plan *structs.Plan) (*structs.PlanResult, State, er
 		allocs = append(allocs, allocList...)
 	}
 
-	// Attach the plan to all the allocations. It is pulled out in the
-	// payload to avoid the redundancy of encoding, but should be denormalized
-	// prior to being inserted into MemDB.
-	if j := plan.Job; j != nil {
-		for _, alloc := range allocs {
-			if alloc.Job == nil {
-				alloc.Job = j
-			}
+	// Set the time the alloc was applied for the first time. This can be used
+	// to approximate the scheduling time.
+	now := time.Now().UTC().UnixNano()
+	for _, alloc := range allocs {
+		if alloc.CreateTime == 0 {
+			alloc.CreateTime = now
 		}
 	}
 
+	// Setup the update request
+	req := structs.ApplyPlanResultsRequest{
+		AllocUpdateRequest: structs.AllocUpdateRequest{
+			Job:   plan.Job,
+			Alloc: allocs,
+		},
+		CreatedDeployment: plan.CreatedDeployment,
+		DeploymentUpdates: plan.DeploymentUpdates,
+	}
+
 	// Apply the full plan
-	err := h.State.UpsertAllocs(index, allocs)
+	err := h.State.UpsertPlanResults(index, &req)
 	return result, nil, err
 }