diff --git a/test/e2e/suite/command/attach.go b/test/e2e/suite/command/attach.go
index 54c35f6c3..41632e0f0 100644
--- a/test/e2e/suite/command/attach.go
+++ b/test/e2e/suite/command/attach.go
@@ -104,6 +104,7 @@ var _ = Describe("Common registry users:", func() {
 			fetched := ORAS("manifest", "fetch", RegistryRef(Host, testRepo, index.Manifests[0].Digest.String())).Exec().Out.Contents()
 			MatchFile(filepath.Join(tempDir, exportName), string(fetched), DefaultTimeout)
 		})
+
 		It("should attach a file via a OCI Image", func() {
 			testRepo := attachTestRepo("image")
 			tempDir := PrepareTempFiles()
@@ -121,6 +122,33 @@ var _ = Describe("Common registry users:", func() {
 			Expect(len(index.Manifests)).To(Equal(1))
 			Expect(index.Manifests[0].MediaType).To(Equal(ocispec.MediaTypeImageManifest))
 		})
+
+		It("should attach file with path validation disabled", func() {
+			testRepo := attachTestRepo("simple")
+			absAttachFileName := filepath.Join(PrepareTempFiles(), foobar.AttachFileName)
+
+			subjectRef := RegistryRef(Host, testRepo, foobar.Tag)
+			prepare(RegistryRef(Host, ImageRepo, foobar.Tag), subjectRef)
+			statusKey := foobar.AttachFileStateKey
+			statusKey.Name = absAttachFileName
+			ORAS("attach", "--artifact-type", "test.attach", subjectRef, fmt.Sprintf("%s:%s", absAttachFileName, foobar.AttachFileMedia), "--disable-path-validation").
+				MatchStatus([]match.StateKey{statusKey}, false, 1).
+				Exec()
+		})
+
+		It("should fail path validation when attaching file with absolute path", func() {
+			testRepo := attachTestRepo("simple")
+			absAttachFileName := filepath.Join(PrepareTempFiles(), foobar.AttachFileName)
+
+			subjectRef := RegistryRef(Host, testRepo, foobar.Tag)
+			prepare(RegistryRef(Host, ImageRepo, foobar.Tag), subjectRef)
+			statusKey := foobar.AttachFileStateKey
+			statusKey.Name = absAttachFileName
+			ORAS("attach", "--artifact-type", "test.attach", subjectRef, fmt.Sprintf("%s:%s", absAttachFileName, foobar.AttachFileMedia)).
+				ExpectFailure().
+				Exec()
+		})
+
 		It("should attach a file via a OCI Artifact", func() {
 			testRepo := attachTestRepo("artifact")
 			tempDir := PrepareTempFiles()
diff --git a/test/e2e/suite/command/push.go b/test/e2e/suite/command/push.go
index dfa56e283..17139fed4 100644
--- a/test/e2e/suite/command/push.go
+++ b/test/e2e/suite/command/push.go
@@ -25,6 +25,7 @@ import (
 	"github.com/onsi/gomega"
 	. "github.com/onsi/gomega"
 	"github.com/onsi/gomega/gbytes"
+	"github.com/opencontainers/go-digest"
 	ocispec "github.com/opencontainers/image-spec/specs-go/v1"
 	"oras.land/oras/test/e2e/internal/testdata/feature"
 	"oras.land/oras/test/e2e/internal/testdata/foobar"
@@ -65,6 +66,39 @@ var _ = Describe("Remote registry users:", func() {
 			Expect(manifest.Layers).Should(ContainElements(foobar.BlobBarDescriptor("application/vnd.oci.image.layer.v1.tar")))
 		})
 
+		It("should push files with path validation disabled", func() {
+			repo := fmt.Sprintf("%s/%s", repoPrefix, "disable-path-validation")
+			ref := RegistryRef(Host, repo, tag)
+			absBarName := filepath.Join(PrepareTempFiles(), foobar.FileBarName)
+
+			ORAS("push", ref, absBarName, "-v", "--disable-path-validation").
+				Exec()
+
+			// validate
+			fetched := ORAS("manifest", "fetch", ref).Exec().Out.Contents()
+			var manifest ocispec.Manifest
+			Expect(json.Unmarshal(fetched, &manifest)).ShouldNot(HaveOccurred())
+			Expect(manifest.Layers).Should(ContainElements(ocispec.Descriptor{
+				MediaType: "application/vnd.oci.image.layer.v1.tar",
+				Digest:    digest.Digest(foobar.BarBlobDigest),
+				Size:      3,
+				Annotations: map[string]string{
+					"org.opencontainers.image.title": absBarName,
+				},
+			}))
+		})
+
+		It("should fail path validation when pushing file with absolute path", func() {
+			repo := fmt.Sprintf("%s/%s", repoPrefix, "path-validation")
+			ref := RegistryRef(Host, repo, tag)
+			absBarName := filepath.Join(PrepareTempFiles(), foobar.FileBarName)
+			// test
+			ORAS("push", ref, absBarName, "-v").
+				MatchErrKeyWords("--disable-path-validation").
+				ExpectFailure().
+				Exec()
+		})
+
 		It("should push files and tag", func() {
 			repo := fmt.Sprintf("%s/%s", repoPrefix, "multi-tag")
 			tempDir := PrepareTempFiles()