diff --git a/pkg/pod/pod.go b/pkg/pod/pod.go
index b038942933a..1f0d3eb856b 100644
--- a/pkg/pod/pod.go
+++ b/pkg/pod/pod.go
@@ -371,7 +371,7 @@ func makeLabels(s *v1beta1.TaskRun) map[string]string {
 	return labels
 }
 
-// shouldAddReadyAnnotationonPodCreate returns a bool indicating whether the
+// shouldAddReadyAnnotationOnPodCreate returns a bool indicating whether the
 // controller should add the `Ready` annotation when creating the Pod. We cannot
 // add the annotation if Tekton is running in a cluster with injected sidecars
 // or if the Task specifies any sidecars.
@@ -401,7 +401,7 @@ func runVolume(i int) corev1.Volume {
 	}
 }
 
-// prepareInitContainers generates a few init containers based of a set of command (in images) and volumes to run
+// entrypointInitContainer generates a few init containers based of a set of command (in images) and volumes to run
 // This should effectively merge multiple command and volumes together.
 func entrypointInitContainer(image string, steps []v1beta1.Step) corev1.Container {
 	// Invoke the entrypoint binary in "cp mode" to copy itself
diff --git a/pkg/pod/pod_test.go b/pkg/pod/pod_test.go
index bc7aee52359..c0a23c4298a 100644
--- a/pkg/pod/pod_test.go
+++ b/pkg/pod/pod_test.go
@@ -1813,6 +1813,69 @@ _EOF_
 }
 
 func TestPodBuildwithAlphaAPIEnabled(t *testing.T) {
+
+	placeScriptsContainer := corev1.Container{
+		Name:         "place-scripts",
+		Image:        "busybox",
+		Command:      []string{"sh"},
+		VolumeMounts: []corev1.VolumeMount{writeScriptsVolumeMount, binMount, debugScriptsVolumeMount},
+		Args: []string{"-c", `tmpfile="/tekton/debug/scripts/debug-continue"
+touch ${tmpfile} && chmod +x ${tmpfile}
+cat > ${tmpfile} << 'debug-continue-heredoc-randomly-generated-9l9zj'
+#!/bin/sh
+set -e
+
+numberOfSteps=1
+debugInfo=/tekton/debug/info
+tektonRun=/tekton/run
+
+postFile="$(ls ${debugInfo} | grep -E '[0-9]+' | tail -1)"
+stepNumber="$(echo ${postFile} | sed 's/[^0-9]*//g')"
+
+if [ $stepNumber -lt $numberOfSteps ]; then
+	touch ${tektonRun}/${stepNumber}/out # Mark step as success
+	echo "0" > ${tektonRun}/${stepNumber}/out.breakpointexit
+	echo "Executing step $stepNumber..."
+else
+	echo "Last step (no. $stepNumber) has already been executed, breakpoint exiting !"
+	exit 0
+fi
+debug-continue-heredoc-randomly-generated-9l9zj
+tmpfile="/tekton/debug/scripts/debug-fail-continue"
+touch ${tmpfile} && chmod +x ${tmpfile}
+cat > ${tmpfile} << 'debug-fail-continue-heredoc-randomly-generated-mz4c7'
+#!/bin/sh
+set -e
+
+numberOfSteps=1
+debugInfo=/tekton/debug/info
+tektonRun=/tekton/run
+
+postFile="$(ls ${debugInfo} | grep -E '[0-9]+' | tail -1)"
+stepNumber="$(echo ${postFile} | sed 's/[^0-9]*//g')"
+
+if [ $stepNumber -lt $numberOfSteps ]; then
+	touch ${tektonRun}/${stepNumber}/out.err # Mark step as a failure
+	echo "1" > ${tektonRun}/${stepNumber}/out.breakpointexit
+	echo "Executing step $stepNumber..."
+else
+	echo "Last step (no. $stepNumber) has already been executed, breakpoint exiting !"
+	exit 0
+fi
+debug-fail-continue-heredoc-randomly-generated-mz4c7
+`},
+	}
+
+	containersVolumeMounts := append([]corev1.VolumeMount{binROMount, runMount(0, false), downwardMount, {
+		Name:      "tekton-creds-init-home-0",
+		MountPath: "/tekton/creds",
+	}}, implicitVolumeMounts...)
+	containersVolumeMounts = append(containersVolumeMounts, debugScriptsVolumeMount)
+	containersVolumeMounts = append(containersVolumeMounts, corev1.VolumeMount{
+		Name:      debugInfoVolumeName,
+		MountPath: filepath.Join(debugInfoDir, fmt.Sprintf("%d", 0)),
+	})
+
 	for _, c := range []struct {
 		desc            string
 		trs             v1beta1.TaskRunSpec
@@ -1836,7 +1899,7 @@ func TestPodBuildwithAlphaAPIEnabled(t *testing.T) {
 		},
 		want: &corev1.PodSpec{
 			RestartPolicy:  corev1.RestartPolicyNever,
-			InitContainers: []corev1.Container{entrypointInitContainer(images.EntrypointImage, []v1beta1.Step{{Name: "name"}})},
+			InitContainers: []corev1.Container{entrypointInitContainer(images.EntrypointImage, []v1beta1.Step{{Name: "name"}}), placeScriptsContainer},
 			Containers: []corev1.Container{{
 				Name:    "step-name",
 				Image:   "image",
@@ -1856,13 +1919,10 @@ func TestPodBuildwithAlphaAPIEnabled(t *testing.T) {
 					"cmd",
 					"--",
 				},
-				VolumeMounts: append([]corev1.VolumeMount{binROMount, runMount(0, false), downwardMount, {
-					Name:      "tekton-creds-init-home-0",
-					MountPath: "/tekton/creds",
-				}}, implicitVolumeMounts...),
+				VolumeMounts:           containersVolumeMounts,
 				TerminationMessagePath: "/tekton/termination",
 			}},
-			Volumes: append(implicitVolumes, debugScriptsVolume, debugInfoVolume, binVolume, runVolume(0), downwardVolume, corev1.Volume{
+			Volumes: append(implicitVolumes, debugScriptsVolume, debugInfoVolume, binVolume, scriptsVolume, runVolume(0), downwardVolume, corev1.Volume{
 				Name:         "tekton-creds-init-home-0",
 				VolumeSource: corev1.VolumeSource{EmptyDir: &corev1.EmptyDirVolumeSource{Medium: corev1.StorageMediumMemory}},
 			}),
diff --git a/pkg/pod/script.go b/pkg/pod/script.go
index 8ca0043f41b..019d4a3e30d 100644
--- a/pkg/pod/script.go
+++ b/pkg/pod/script.go
@@ -130,9 +130,18 @@ func convertScripts(shellImageLinux string, shellImageWin string, steps []v1beta
 func convertListOfSteps(steps []v1beta1.Step, initContainer *corev1.Container, placeScripts *bool, breakpoints []string, namePrefix string) []corev1.Container {
 	containers := []corev1.Container{}
 	for i, s := range steps {
+		// Add debug mounts if breakpoints are present
+		if len(breakpoints) > 0 {
+			debugInfoVolumeMount := corev1.VolumeMount{
+				Name:      debugInfoVolumeName,
+				MountPath: filepath.Join(debugInfoDir, fmt.Sprintf("%d", i)),
+			}
+			steps[i].VolumeMounts = append(steps[i].VolumeMounts, debugScriptsVolumeMount, debugInfoVolumeMount)
+		}
+
 		if s.Script == "" {
 			// Nothing to convert.
-			containers = append(containers, *s.ToK8sContainer())
+			containers = append(containers, *steps[i].ToK8sContainer())
 			continue
 		}
 
@@ -187,19 +196,15 @@ cat > ${scriptfile} << '%s'
 		}
 		steps[i].VolumeMounts = append(steps[i].VolumeMounts, scriptsVolumeMount)
 
-		// Add debug mounts if breakpoints are present
-		if len(breakpoints) > 0 {
-			debugInfoVolumeMount := corev1.VolumeMount{
-				Name:      debugInfoVolumeName,
-				MountPath: filepath.Join(debugInfoDir, fmt.Sprintf("%d", i)),
-			}
-			steps[i].VolumeMounts = append(steps[i].VolumeMounts, debugScriptsVolumeMount, debugInfoVolumeMount)
-		}
 		containers = append(containers, *steps[i].ToK8sContainer())
 	}
 
 	// Place debug scripts if breakpoints are enabled
 	if len(breakpoints) > 0 {
+		// If breakpoint is not nil then should add the init container
+		// to write debug script files
+		*placeScripts = true
+
 		type script struct {
 			name    string
 			content string
diff --git a/pkg/pod/script_test.go b/pkg/pod/script_test.go
index 6ab62821422..0aa51d5144b 100644
--- a/pkg/pod/script_test.go
+++ b/pkg/pod/script_test.go
@@ -227,6 +227,7 @@ script-3`,
 	}}, []v1beta1.Sidecar{}, &v1beta1.TaskRunDebug{
 		Breakpoint: []string{breakpointOnFailure},
 	})
+
 	wantInit := &corev1.Container{
 		Name:    "place-scripts",
 		Image:   images.ShellImage,
@@ -296,19 +297,24 @@ debug-fail-continue-heredoc-randomly-generated-6nl7g
 `},
 		VolumeMounts: []corev1.VolumeMount{writeScriptsVolumeMount, binMount, debugScriptsVolumeMount},
 	}
+
 	want := []corev1.Container{{
 		Image:   "step-1",
 		Command: []string{"/tekton/scripts/script-0-9l9zj"},
-		VolumeMounts: []corev1.VolumeMount{scriptsVolumeMount, debugScriptsVolumeMount,
-			{Name: debugInfoVolumeName, MountPath: "/tekton/debug/info/0"}},
+		VolumeMounts: []corev1.VolumeMount{debugScriptsVolumeMount,
+			{Name: debugInfoVolumeName, MountPath: "/tekton/debug/info/0"}, scriptsVolumeMount},
 	}, {
 		Image: "step-2",
+		VolumeMounts: []corev1.VolumeMount{
+			debugScriptsVolumeMount, {Name: debugInfoVolumeName, MountPath: "/tekton/debug/info/1"},
+		},
 	}, {
 		Image:   "step-3",
 		Command: []string{"/tekton/scripts/script-2-mz4c7"},
 		Args:    []string{"my", "args"},
-		VolumeMounts: append(preExistingVolumeMounts, scriptsVolumeMount, debugScriptsVolumeMount,
-			corev1.VolumeMount{Name: debugInfoVolumeName, MountPath: "/tekton/debug/info/2"}),
+		VolumeMounts: append(preExistingVolumeMounts, debugScriptsVolumeMount,
+			corev1.VolumeMount{Name: debugInfoVolumeName, MountPath: "/tekton/debug/info/2"},
+			scriptsVolumeMount),
 	}, {
 		Image:   "step-3",
 		Command: []string{"/tekton/scripts/script-3-mssqb"},
@@ -316,13 +322,16 @@ debug-fail-continue-heredoc-randomly-generated-6nl7g
 		VolumeMounts: []corev1.VolumeMount{
 			{Name: "pre-existing-volume-mount", MountPath: "/mount/path"},
 			{Name: "another-one", MountPath: "/another/one"},
-			scriptsVolumeMount, debugScriptsVolumeMount,
+			debugScriptsVolumeMount,
 			{Name: debugInfoVolumeName, MountPath: "/tekton/debug/info/3"},
+			scriptsVolumeMount,
 		},
 	}}
+
 	if d := cmp.Diff(wantInit, gotInit); d != "" {
 		t.Errorf("Init Container Diff %s", diff.PrintWantGot(d))
 	}
+
 	if d := cmp.Diff(want, gotSteps); d != "" {
 		t.Errorf("Containers Diff %s", diff.PrintWantGot(d))
 	}