diff --git a/cmd/workingdirinit/main.go b/cmd/workingdirinit/main.go
index a131ff49b69..5c85281c54d 100644
--- a/cmd/workingdirinit/main.go
+++ b/cmd/workingdirinit/main.go
@@ -17,6 +17,8 @@ limitations under the License.
 package main
 
 import (
+	"fmt"
+	"io/fs"
 	"log"
 	"os"
 	"path/filepath"
@@ -24,6 +26,77 @@ import (
 	"strings"
 )
 
+// exists returns whether the given file or directory exists
+func exists(path string) (bool, error) {
+	_, err := os.Stat(path)
+	if err == nil {
+		return true, nil
+	}
+	if os.IsNotExist(err) {
+		return false, nil
+	}
+	return false, err
+}
+
+func getPermissions(path string) (fs.FileMode, error) {
+	fileInfo, err := os.Stat(path)
+	if err != nil {
+		return fs.FileMode(0o666), err
+	}
+	return fileInfo.Mode(), nil
+}
+
+func createPath(path string) error {
+	// Check if the path already exists.
+	ex, err := exists(path)
+	if err != nil {
+		return fmt.Errorf("error accessing path %s: %w", path, err)
+	}
+	// Path already exists, so no subdirectory to create. Skip the rest.
+	if ex {
+		return nil
+	}
+	// Find the innermost parent directory to get the permissions to apply to the child directories.
+	parts := strings.Split(path, string(filepath.Separator))
+
+	// Walk in reverse order until we find the path of the innermost parent directory that exists.
+	for i := len(parts) - 1; i > 0; i-- {
+		dir := filepath.Join(string(filepath.Separator), filepath.Join(parts[:i]...))
+
+		// backtracked and reached the root "/". Means that this was not a mount. Let kubernetes handle it.
+		if dir == string(filepath.Separator) {
+			return nil
+		}
+		// Check if the immediate parent path exists
+		ex, err := exists(dir)
+		if err != nil {
+			return fmt.Errorf("error accessing path %s: %w", dir, err)
+		}
+		// Found the innermost parent directory that exists.
+		if ex {
+			// We need to get its permissions and apply it to the child directories.
+			perm, err := getPermissions(dir)
+			if err != nil {
+				return fmt.Errorf("error accessing path %s: %w", dir, err)
+			}
+			// Create the path
+			if err := os.MkdirAll(path, perm); err != nil {
+				return fmt.Errorf("failed to mkdir %q: %w", path, err)
+			}
+			// walk up again and set the permissions of the parent to the child directories
+			d := dir
+			for j := i; j < len(parts); j++ {
+				d = filepath.Join(d, parts[j])
+				if err := os.Chmod(d, perm); err != nil {
+					return fmt.Errorf("failed to chmod %q: %w", d, err)
+				}
+			}
+			return nil
+		}
+	}
+	return nil
+}
+
 func main() {
 	for i, d := range os.Args {
 		// os.Args[0] is the path to this executable, so we should skip it
@@ -34,10 +107,14 @@ func main() {
 		ws := cleanPath("/workspace/")
 		p := cleanPath(d)
 
-		if !filepath.IsAbs(p) || strings.HasPrefix(p, ws+string(filepath.Separator)) {
-			if err := os.MkdirAll(p, 0755); err != nil {
-				log.Fatalf("Failed to mkdir %q: %v", p, err)
-			}
+		// Only handles relative path inside `/workspace` for backwards compatibility.
+		if !filepath.IsAbs(p) {
+			p = filepath.Join(ws, p)
+		}
+
+		err := createPath(p)
+		if err != nil {
+			log.Fatalf("Failed to create path %s: %v", p, err)
 		}
 	}
 }
diff --git a/pkg/pod/pod_test.go b/pkg/pod/pod_test.go
index 2917333a4f1..87554e4cea6 100644
--- a/pkg/pod/pod_test.go
+++ b/pkg/pod/pod_test.go
@@ -473,7 +473,6 @@ func TestPodBuild(t *testing.T) {
 						Image:        images.WorkingDirInitImage,
 						Command:      []string{"/ko-app/workingdirinit"},
 						Args:         []string{filepath.Join(pipeline.WorkspaceDir, "test")},
-						WorkingDir:   pipeline.WorkspaceDir,
 						VolumeMounts: implicitVolumeMounts,
 					},
 				},
diff --git a/pkg/pod/workingdir_init.go b/pkg/pod/workingdir_init.go
index af001dc104d..0065d412ccb 100644
--- a/pkg/pod/workingdir_init.go
+++ b/pkg/pod/workingdir_init.go
@@ -18,11 +18,8 @@ package pod
 
 import (
 	"path/filepath"
-	"strings"
 
-	"github.com/tektoncd/pipeline/pkg/apis/pipeline"
 	corev1 "k8s.io/api/core/v1"
-	"k8s.io/apimachinery/pkg/util/sets"
 )
 
 // workingDirInit returns a Container that should be run as an init
@@ -37,26 +34,24 @@ import (
 // so that the correct security context can be applied.
 func workingDirInit(workingdirinitImage string, stepContainers []corev1.Container, setSecurityContext, windows bool) *corev1.Container {
 	// Gather all unique workingDirs.
-	workingDirs := sets.NewString()
+	workingDirs := []string{}
+	vms := implicitVolumeMounts
+	// To ensure that we don't duplicate volume mounts
+	requestedVolumeMounts := map[string]bool{}
 	for _, step := range stepContainers {
 		if step.WorkingDir != "" {
-			workingDirs.Insert(step.WorkingDir)
+			workingDirs = append(workingDirs, filepath.Clean(step.WorkingDir))
 		}
-	}
-	if workingDirs.Len() == 0 {
-		return nil
-	}
-
-	// Clean and append each relative workingDir.
-	var relativeDirs []string
-	for _, wd := range workingDirs.List() {
-		p := filepath.Clean(wd)
-		if !filepath.IsAbs(p) || strings.HasPrefix(p, "/workspace/") {
-			relativeDirs = append(relativeDirs, p)
+		for _, vm := range step.VolumeMounts {
+			// Only add unique volume mounts from Steps
+			if !requestedVolumeMounts[filepath.Clean(vm.MountPath)] {
+				vms = append(vms, vm)
+				requestedVolumeMounts[filepath.Clean(vm.MountPath)] = true
+			}
 		}
 	}
 
-	if len(relativeDirs) == 0 {
+	if len(workingDirs) == 0 {
 		// There are no workingDirs to initialize.
 		return nil
 	}
@@ -69,9 +64,8 @@ func workingDirInit(workingdirinitImage string, stepContainers []corev1.Containe
 		Name:         "working-dir-initializer",
 		Image:        workingdirinitImage,
 		Command:      []string{"/ko-app/workingdirinit"},
-		Args:         relativeDirs,
-		WorkingDir:   pipeline.WorkspaceDir,
-		VolumeMounts: implicitVolumeMounts,
+		Args:         workingDirs,
+		VolumeMounts: vms,
 	}
 	if setSecurityContext {
 		c.SecurityContext = securityContext
diff --git a/pkg/pod/workingdir_init_test.go b/pkg/pod/workingdir_init_test.go
index 05f1f65f133..0df90337f07 100644
--- a/pkg/pod/workingdir_init_test.go
+++ b/pkg/pod/workingdir_init_test.go
@@ -20,7 +20,6 @@ import (
 	"testing"
 
 	"github.com/google/go-cmp/cmp"
-	"github.com/tektoncd/pipeline/pkg/apis/pipeline"
 	"github.com/tektoncd/pipeline/test/diff"
 	"github.com/tektoncd/pipeline/test/names"
 	corev1 "k8s.io/api/core/v1"
@@ -41,7 +40,7 @@ func TestWorkingDirInit(t *testing.T) {
 		}},
 		want: nil,
 	}, {
-		desc: "workingDirs are unique and sorted, absolute dirs are ignored",
+		desc: "workingDirs are unique and sorted",
 		stepContainers: []corev1.Container{{
 			WorkingDir: "zzz",
 		}, {
@@ -61,12 +60,11 @@ func TestWorkingDirInit(t *testing.T) {
 			Name:         "working-dir-initializer",
 			Image:        images.WorkingDirInitImage,
 			Command:      []string{"/ko-app/workingdirinit"},
-			Args:         []string{"/workspace/bbb", "aaa", "zzz"},
-			WorkingDir:   pipeline.WorkspaceDir,
+			Args:         []string{"zzz", "aaa", "/ignored", "/workspace", "zzz", "/workspace/bbb"},
 			VolumeMounts: implicitVolumeMounts,
 		},
 	}, {
-		desc: "workingDirs are unique and sorted, absolute dirs are ignored, + securitycontext",
+		desc: "workingDirs are unique and sorted + securitycontext",
 		stepContainers: []corev1.Container{{
 			WorkingDir: "zzz",
 		}, {
@@ -87,13 +85,12 @@ func TestWorkingDirInit(t *testing.T) {
 			Name:            "working-dir-initializer",
 			Image:           images.WorkingDirInitImage,
 			Command:         []string{"/ko-app/workingdirinit"},
-			Args:            []string{"/workspace/bbb", "aaa", "zzz"},
-			WorkingDir:      pipeline.WorkspaceDir,
+			Args:            []string{"zzz", "aaa", "/ignored", "/workspace", "zzz", "/workspace/bbb"},
 			VolumeMounts:    implicitVolumeMounts,
 			SecurityContext: linuxSecurityContext,
 		},
 	}, {
-		desc: "workingDirs are unique and sorted, absolute dirs are ignored, uses windows",
+		desc: "workingDirs are unique and sorted, uses windows",
 		stepContainers: []corev1.Container{{
 			WorkingDir: "zzz",
 		}, {
@@ -114,12 +111,11 @@ func TestWorkingDirInit(t *testing.T) {
 			Name:         "working-dir-initializer",
 			Image:        images.WorkingDirInitImage,
 			Command:      []string{"/ko-app/workingdirinit"},
-			Args:         []string{"/workspace/bbb", "aaa", "zzz"},
-			WorkingDir:   pipeline.WorkspaceDir,
+			Args:         []string{"zzz", "aaa", "/ignored", "/workspace", "zzz", "/workspace/bbb"},
 			VolumeMounts: implicitVolumeMounts,
 		},
 	}, {
-		desc: "workingDirs are unique and sorted, absolute dirs are ignored, uses windows, + securityContext",
+		desc: "workingDirs are unique and sorted, uses windows, + securityContext",
 		stepContainers: []corev1.Container{{
 			WorkingDir: "zzz",
 		}, {
@@ -141,8 +137,7 @@ func TestWorkingDirInit(t *testing.T) {
 			Name:            "working-dir-initializer",
 			Image:           images.WorkingDirInitImage,
 			Command:         []string{"/ko-app/workingdirinit"},
-			Args:            []string{"/workspace/bbb", "aaa", "zzz"},
-			WorkingDir:      pipeline.WorkspaceDir,
+			Args:            []string{"zzz", "aaa", "/ignored", "/workspace", "zzz", "/workspace/bbb"},
 			VolumeMounts:    implicitVolumeMounts,
 			SecurityContext: windowsSecurityContext,
 		},