diff --git a/pkg/reconciler/pipelinerun/pipelinerun.go b/pkg/reconciler/pipelinerun/pipelinerun.go
index f6687352742..eaa5b4baf10 100644
--- a/pkg/reconciler/pipelinerun/pipelinerun.go
+++ b/pkg/reconciler/pipelinerun/pipelinerun.go
@@ -524,6 +524,9 @@ func (c *Reconciler) reconcile(ctx context.Context, pr *v1beta1.PipelineRun, get
 		return err
 	}
 
+	// Reset the skipped status to trigger recalculation
+	pipelineRunFacts.ResetSkippedCache()
+
 	after := pipelineRunFacts.GetPipelineConditionStatus(pr, logger)
 	switch after.Status {
 	case corev1.ConditionTrue:
@@ -565,6 +568,9 @@ func (c *Reconciler) runNextSchedulableTask(ctx context.Context, pr *v1beta1.Pip
 	}
 
 	resources.ApplyTaskResults(nextRprts, resolvedResultRefs)
+	// After we apply Task Results, we may be able to evaluate more
+	// when expressions, so reset the skipped cache
+	pipelineRunFacts.ResetSkippedCache()
 
 	// GetFinalTasks only returns tasks when a DAG is complete
 	nextRprts = append(nextRprts, pipelineRunFacts.GetFinalTasks()...)
diff --git a/pkg/reconciler/pipelinerun/resources/pipelinerunresolution.go b/pkg/reconciler/pipelinerun/resources/pipelinerunresolution.go
index 787a89a1ef8..96c51576f8c 100644
--- a/pkg/reconciler/pipelinerun/resources/pipelinerunresolution.go
+++ b/pkg/reconciler/pipelinerun/resources/pipelinerunresolution.go
@@ -133,13 +133,7 @@ func (t *ResolvedPipelineRunTask) checkParentsDone(facts *PipelineRunFacts) bool
 	return true
 }
 
-// Skip returns true if a PipelineTask will not be run because
-// (1) its When Expressions evaluated to false
-// (2) its Condition Checks failed
-// (3) its parent task was skipped
-// (4) Pipeline is in stopping state (one of the PipelineTasks failed)
-// Note that this means Skip returns false if a conditionCheck is in progress
-func (t *ResolvedPipelineRunTask) Skip(facts *PipelineRunFacts) bool {
+func (t *ResolvedPipelineRunTask) skip(facts *PipelineRunFacts) bool {
 	if facts.isFinalTask(t.PipelineTask.Name) || t.IsStarted() {
 		return false
 	}
@@ -151,6 +145,22 @@ func (t *ResolvedPipelineRunTask) Skip(facts *PipelineRunFacts) bool {
 	return false
 }
 
+// Skip returns true if a PipelineTask will not be run because
+// (1) its When Expressions evaluated to false
+// (2) its Condition Checks failed
+// (3) its parent task was skipped
+// (4) Pipeline is in stopping state (one of the PipelineTasks failed)
+// Note that this means Skip returns false if a conditionCheck is in progress
+func (t *ResolvedPipelineRunTask) Skip(facts *PipelineRunFacts) bool {
+	if facts.SkipCache == nil {
+		facts.SkipCache = make(map[string]bool)
+	}
+	if _, cached := facts.SkipCache[t.PipelineTask.Name]; !cached {
+		facts.SkipCache[t.PipelineTask.Name] = t.skip(facts) // t.skip() is same as our existing t.Skip()
+	}
+	return facts.SkipCache[t.PipelineTask.Name]
+}
+
 func (t *ResolvedPipelineRunTask) conditionsSkip() bool {
 	if len(t.ResolvedConditionChecks) > 0 {
 		if t.ResolvedConditionChecks.IsDone() && !t.ResolvedConditionChecks.IsSuccess() {
diff --git a/pkg/reconciler/pipelinerun/resources/pipelinerunstate.go b/pkg/reconciler/pipelinerun/resources/pipelinerunstate.go
index f9a5e965d70..80a483d1268 100644
--- a/pkg/reconciler/pipelinerun/resources/pipelinerunstate.go
+++ b/pkg/reconciler/pipelinerun/resources/pipelinerunstate.go
@@ -37,6 +37,16 @@ type PipelineRunFacts struct {
 	State           PipelineRunState
 	TasksGraph      *dag.Graph
 	FinalTasksGraph *dag.Graph
+
+	// SkipCache is a hash of PipelineTask names that stores whether a task will be
+	// executed or not, because it's either not reachable via the DAG due to the pipeline
+	// state, or because it has failed conditions.
+	// We cache this data along the state, because it's expensive to compute, it requires
+	// traversing potentially the whole graph; this way it can built incrementally, when
+	// needed, via the `Skip` method in pipelinerunresolution.go
+	// The skip data is sensitive to changes in the state. The ResetSkippedCache method
+	// can be used to clean the cache and force re-computation when needed.
+	SkipCache map[string]bool
 }
 
 // pipelineRunStatusCount holds the count of successful, failed, cancelled, skipped, and incomplete tasks
@@ -53,6 +63,11 @@ type pipelineRunStatusCount struct {
 	Incomplete int
 }
 
+// ResetSkippedCache resets the skipped cache in the facts map
+func (facts *PipelineRunFacts) ResetSkippedCache() {
+	facts.SkipCache = make(map[string]bool)
+}
+
 // ToMap returns a map that maps pipeline task name to the resolved pipeline run task
 func (state PipelineRunState) ToMap() map[string]*ResolvedPipelineRunTask {
 	m := make(map[string]*ResolvedPipelineRunTask)
diff --git a/pkg/reconciler/pipelinerun/resources/pipelinerunstate_test.go b/pkg/reconciler/pipelinerun/resources/pipelinerunstate_test.go
index 0407c89f19e..86bad2ce4b0 100644
--- a/pkg/reconciler/pipelinerun/resources/pipelinerunstate_test.go
+++ b/pkg/reconciler/pipelinerun/resources/pipelinerunstate_test.go
@@ -17,6 +17,7 @@ limitations under the License.
 package resources
 
 import (
+	"fmt"
 	"testing"
 	"time"
 
@@ -408,6 +409,7 @@ func TestGetNextTaskWithRetries(t *testing.T) {
 }
 
 func TestPipelineRunState_SuccessfulOrSkippedDAGTasks(t *testing.T) {
+	largePipelineState := buildPipelineStateWithLargeDepencyGraph(t)
 	tcs := []struct {
 		name          string
 		state         PipelineRunState
@@ -454,6 +456,10 @@ func TestPipelineRunState_SuccessfulOrSkippedDAGTasks(t *testing.T) {
 			"not skipped since it failed",
 		state:         conditionCheckFailedWithOthersFailedState,
 		expectedNames: []string{pts[5].Name},
+	}, {
+		name:          "large deps, not started",
+		state:         largePipelineState,
+		expectedNames: []string{},
 	}}
 	for _, tc := range tcs {
 		t.Run(tc.name, func(t *testing.T) {
@@ -474,6 +480,65 @@ func TestPipelineRunState_SuccessfulOrSkippedDAGTasks(t *testing.T) {
 	}
 }
 
+func buildPipelineStateWithLargeDepencyGraph(t *testing.T) PipelineRunState {
+	t.Helper()
+	var task = &v1beta1.Task{
+		ObjectMeta: metav1.ObjectMeta{
+			Name: "task",
+		},
+		Spec: v1beta1.TaskSpec{
+			Steps: []v1beta1.Step{{Container: corev1.Container{
+				Name: "step1",
+			}}},
+		},
+	}
+	var pipelineRunState PipelineRunState
+	pipelineRunState = []*ResolvedPipelineRunTask{{
+		PipelineTask: &v1beta1.PipelineTask{
+			Name:    "t1",
+			TaskRef: &v1beta1.TaskRef{Name: "task"},
+		},
+		TaskRun: nil,
+		ResolvedTaskResources: &resources.ResolvedTaskResources{
+			TaskSpec: &task.Spec,
+		},
+	}}
+	for i := 2; i < 60; i++ {
+		dependFrom := 1
+		if i > 10 {
+			if i%10 == 0 {
+				dependFrom = i - 10
+			} else {
+				dependFrom = i - (i % 10)
+			}
+		}
+		params := []v1beta1.Param{}
+		var alpha byte
+		for alpha = 'a'; alpha <= 'j'; alpha++ {
+			params = append(params, v1beta1.Param{
+				Name: fmt.Sprintf("%c", alpha),
+				Value: v1beta1.ArrayOrString{
+					Type:      v1beta1.ParamTypeString,
+					StringVal: fmt.Sprintf("$(tasks.t%d.results.%c)", dependFrom, alpha),
+				},
+			})
+		}
+		pipelineRunState = append(pipelineRunState, &ResolvedPipelineRunTask{
+			PipelineTask: &v1beta1.PipelineTask{
+				Name:    fmt.Sprintf("t%d", i),
+				Params:  params,
+				TaskRef: &v1beta1.TaskRef{Name: "task"},
+			},
+			TaskRun: nil,
+			ResolvedTaskResources: &resources.ResolvedTaskResources{
+				TaskSpec: &task.Spec,
+			},
+		},
+		)
+	}
+	return pipelineRunState
+}
+
 func TestPipelineRunState_GetFinalTasks(t *testing.T) {
 	tcs := []struct {
 		name               string