diff --git a/scheduler/generic_sched.go b/scheduler/generic_sched.go
index 0339b02441c..68f0d3c4720 100644
--- a/scheduler/generic_sched.go
+++ b/scheduler/generic_sched.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"log"
 
+	"github.com/hashicorp/go-multierror"
 	"github.com/hashicorp/nomad/nomad/structs"
 )
 
@@ -50,11 +51,12 @@ type GenericScheduler struct {
 	planner Planner
 	batch   bool
 
-	eval  *structs.Evaluation
-	job   *structs.Job
-	plan  *structs.Plan
-	ctx   *EvalContext
-	stack *GenericStack
+	eval       *structs.Evaluation
+	job        *structs.Job
+	plan       *structs.Plan
+	planResult *structs.PlanResult
+	ctx        *EvalContext
+	stack      *GenericStack
 
 	limitReached bool
 	nextEval     *structs.Evaluation
@@ -99,14 +101,24 @@ func (s *GenericScheduler) Process(eval *structs.Evaluation) error {
 		return setStatus(s.logger, s.planner, s.eval, s.nextEval, structs.EvalStatusFailed, desc)
 	}
 
-	// Retry up to the maxScheduleAttempts
+	// Retry up to the maxScheduleAttempts and reset if progress is made.
+	progress := func() bool { return progressMade(s.planResult) }
 	limit := maxServiceScheduleAttempts
 	if s.batch {
 		limit = maxBatchScheduleAttempts
 	}
-	if err := retryMax(limit, s.process); err != nil {
+	if err := retryMax(limit, s.process, progress); err != nil {
 		if statusErr, ok := err.(*SetStatusError); ok {
-			return setStatus(s.logger, s.planner, s.eval, s.nextEval, statusErr.EvalStatus, err.Error())
+			// Scheduling was tried but made no forward progress so create a
+			// blocked eval to retry once resources become available.
+			var mErr multierror.Error
+			if err := s.createBlockedEval(); err != nil {
+				mErr.Errors = append(mErr.Errors, err)
+			}
+			if err := setStatus(s.logger, s.planner, s.eval, s.nextEval, statusErr.EvalStatus, err.Error()); err != nil {
+				mErr.Errors = append(mErr.Errors, err)
+			}
+			return mErr.ErrorOrNil()
 		}
 		return err
 	}
@@ -115,6 +127,21 @@ func (s *GenericScheduler) Process(eval *structs.Evaluation) error {
 	return setStatus(s.logger, s.planner, s.eval, s.nextEval, structs.EvalStatusComplete, "")
 }
 
+// createBlockedEval creates a blocked eval and stores it.
+func (s *GenericScheduler) createBlockedEval() error {
+	e := s.ctx.Eligibility()
+	escaped := e.HasEscaped()
+
+	// Only store the eligible classes if the eval hasn't escaped.
+	var classEligibility map[string]bool
+	if !escaped {
+		classEligibility = e.GetClasses()
+	}
+
+	s.blocked = s.eval.BlockedEval(classEligibility, escaped)
+	return s.planner.CreateEval(s.blocked)
+}
+
 // process is wrapped in retryMax to iteratively run the handler until we have no
 // further work or we've made the maximum number of attempts.
 func (s *GenericScheduler) process() (bool, error) {
@@ -163,18 +190,16 @@ func (s *GenericScheduler) process() (bool, error) {
 	// If there are failed allocations, we need to create a blocked evaluation
 	// to place the failed allocations when resources become available.
 	if len(s.plan.FailedAllocs) != 0 && s.blocked == nil {
-		e := s.ctx.Eligibility()
-		classes := e.GetClasses()
-		s.blocked = s.eval.BlockedEval(classes, e.HasEscaped())
-		if err := s.planner.CreateEval(s.blocked); err != nil {
+		if err := s.createBlockedEval(); err != nil {
 			s.logger.Printf("[ERR] sched: %#v failed to make blocked eval: %v", s.eval, err)
 			return false, err
 		}
 		s.logger.Printf("[DEBUG] sched: %#v: failed to place all allocations, blocked eval '%s' created", s.eval, s.blocked.ID)
 	}
 
-	// Submit the plan
+	// Submit the plan and store the results.
 	result, newState, err := s.planner.SubmitPlan(s.plan)
+	s.planResult = result
 	if err != nil {
 		return false, err
 	}
diff --git a/scheduler/system_sched.go b/scheduler/system_sched.go
index 9b352b81fb1..4bd789c71ea 100644
--- a/scheduler/system_sched.go
+++ b/scheduler/system_sched.go
@@ -25,13 +25,14 @@ type SystemScheduler struct {
 	state   State
 	planner Planner
 
-	eval      *structs.Evaluation
-	job       *structs.Job
-	plan      *structs.Plan
-	ctx       *EvalContext
-	stack     *SystemStack
-	nodes     []*structs.Node
-	nodesByDC map[string]int
+	eval       *structs.Evaluation
+	job        *structs.Job
+	plan       *structs.Plan
+	planResult *structs.PlanResult
+	ctx        *EvalContext
+	stack      *SystemStack
+	nodes      []*structs.Node
+	nodesByDC  map[string]int
 
 	limitReached bool
 	nextEval     *structs.Evaluation
@@ -62,8 +63,9 @@ func (s *SystemScheduler) Process(eval *structs.Evaluation) error {
 		return setStatus(s.logger, s.planner, s.eval, s.nextEval, structs.EvalStatusFailed, desc)
 	}
 
-	// Retry up to the maxSystemScheduleAttempts
-	if err := retryMax(maxSystemScheduleAttempts, s.process); err != nil {
+	// Retry up to the maxSystemScheduleAttempts and reset if progress is made.
+	progress := func() bool { return progressMade(s.planResult) }
+	if err := retryMax(maxSystemScheduleAttempts, s.process, progress); err != nil {
 		if statusErr, ok := err.(*SetStatusError); ok {
 			return setStatus(s.logger, s.planner, s.eval, s.nextEval, statusErr.EvalStatus, err.Error())
 		}
@@ -129,6 +131,7 @@ func (s *SystemScheduler) process() (bool, error) {
 
 	// Submit the plan
 	result, newState, err := s.planner.SubmitPlan(s.plan)
+	s.planResult = result
 	if err != nil {
 		return false, err
 	}
diff --git a/scheduler/util.go b/scheduler/util.go
index 29fed93427f..2e90a5ea923 100644
--- a/scheduler/util.go
+++ b/scheduler/util.go
@@ -208,8 +208,10 @@ func readyNodesInDCs(state State, dcs []string) ([]*structs.Node, map[string]int
 }
 
 // retryMax is used to retry a callback until it returns success or
-// a maximum number of attempts is reached
-func retryMax(max int, cb func() (bool, error)) error {
+// a maximum number of attempts is reached. An optional reset function may be
+// passed which is called after each failed iteration. If the reset function is
+// set and returns true, the number of attempts is reset back to max.
+func retryMax(max int, cb func() (bool, error), reset func() bool) error {
 	attempts := 0
 	for attempts < max {
 		done, err := cb()
@@ -219,7 +221,13 @@ func retryMax(max int, cb func() (bool, error)) error {
 		if done {
 			return nil
 		}
-		attempts += 1
+
+		// Check if we should reset the number attempts
+		if reset != nil && reset() {
+			attempts = 0
+		} else {
+			attempts += 1
+		}
 	}
 	return &SetStatusError{
 		Err:        fmt.Errorf("maximum attempts reached (%d)", max),
@@ -227,6 +235,13 @@ func retryMax(max int, cb func() (bool, error)) error {
 	}
 }
 
+// progressMade checks to see if the plan result made allocations or updates.
+// If the result is nil, false is returned.
+func progressMade(result *structs.PlanResult) bool {
+	return result != nil && len(result.NodeUpdate) != 0 &&
+		len(result.NodeAllocation) != 0
+}
+
 // taintedNodes is used to scan the allocations and then check if the
 // underlying nodes are tainted, and should force a migration of the allocation.
 func taintedNodes(state State, allocs []*structs.Allocation) (map[string]bool, error) {
diff --git a/scheduler/util_test.go b/scheduler/util_test.go
index 104f7461ed3..86adcc9366b 100644
--- a/scheduler/util_test.go
+++ b/scheduler/util_test.go
@@ -229,7 +229,7 @@ func TestRetryMax(t *testing.T) {
 		calls += 1
 		return false, nil
 	}
-	err := retryMax(3, bad)
+	err := retryMax(3, bad, nil)
 	if err == nil {
 		t.Fatalf("should fail")
 	}
@@ -237,12 +237,29 @@ func TestRetryMax(t *testing.T) {
 		t.Fatalf("mis match")
 	}
 
+	calls = 0
+	first := true
+	reset := func() bool {
+		if calls == 3 && first {
+			first = false
+			return true
+		}
+		return false
+	}
+	err = retryMax(3, bad, reset)
+	if err == nil {
+		t.Fatalf("should fail")
+	}
+	if calls != 6 {
+		t.Fatalf("mis match")
+	}
+
 	calls = 0
 	good := func() (bool, error) {
 		calls += 1
 		return true, nil
 	}
-	err = retryMax(3, good)
+	err = retryMax(3, good, nil)
 	if err != nil {
 		t.Fatalf("err: %v", err)
 	}