diff --git a/cmd/cosign/cli/download/sbom.go b/cmd/cosign/cli/download/sbom.go
index eb362a9624a..ba6208c704d 100644
--- a/cmd/cosign/cli/download/sbom.go
+++ b/cmd/cosign/cli/download/sbom.go
@@ -36,43 +36,33 @@ func SBOMCmd(ctx context.Context, regOpts options.RegistryOptions, imageRef stri
 	if err != nil {
 		return nil, err
 	}
-	ociremoteOpts = append(ociremoteOpts,
-		// TODO(mattmoor): This isn't really "signatures", consider shifting to
-		// an SBOMs accessor?
-		ociremote.WithSignatureSuffix(ociremote.SBOMTagSuffix))
 
 	se, err := ociremote.SignedEntity(ref, ociremoteOpts...)
 	if err != nil {
 		return nil, err
 	}
 
-	// TODO(mattmoor): This logic does a shallow walk, we should use `mutate.Map`
-	// if we want to collect all of the SBOMs attached at any level of an index.
-	img, err := se.Signatures()
+	file, err := se.Attachment("sbom")
 	if err != nil {
 		return nil, err
 	}
-	sigs, err := img.Get()
+
+	// "attach sbom" attaches a single static.NewFile
+	sboms := make([]string, 0, 1)
+
+	mt, err := file.FileMediaType()
 	if err != nil {
 		return nil, err
 	}
-	if len(sigs) == 0 {
-		return nil, fmt.Errorf("no signatures associated with %v", ref)
-	}
 
-	sboms := make([]string, 0, len(sigs))
-	for _, l := range sigs {
-		mt, err := l.MediaType()
-		if err != nil {
-			return nil, err
-		}
-		fmt.Fprintf(os.Stderr, "Found SBOM of media type: %s\n", mt)
-		sbom, err := l.Payload()
-		if err != nil {
-			return nil, err
-		}
-		sboms = append(sboms, string(sbom))
-		fmt.Fprintln(out, string(sbom))
+	fmt.Fprintf(os.Stderr, "Found SBOM of media type: %s\n", mt)
+	sbom, err := file.Payload()
+	if err != nil {
+		return nil, err
 	}
+
+	sboms = append(sboms, string(sbom))
+	fmt.Fprintln(out, string(sbom))
+
 	return sboms, nil
 }
diff --git a/cmd/cosign/cli/sign/sign.go b/cmd/cosign/cli/sign/sign.go
index 073303fb7e2..9139423dd35 100644
--- a/cmd/cosign/cli/sign/sign.go
+++ b/cmd/cosign/cli/sign/sign.go
@@ -174,35 +174,35 @@ func SignCmd(ctx context.Context, ko KeyOpts, regOpts options.RegistryOptions, a
 		if digest, ok := ref.(name.Digest); ok && !recursive {
 			se, err := ociempty.SignedImage(ref)
 			if err != nil {
-				return err
+				return errors.Wrap(err, "accessing image")
 			}
 			err = signDigest(ctx, digest, staticPayload, ko, regOpts, annotations, upload, force, dd, sv, se)
 			if err != nil {
-				return err
+				return errors.Wrap(err, "signing digest")
 			}
 			continue
 		}
 
 		se, err := ociremote.SignedEntity(ref, opts...)
 		if err != nil {
-			return err
+			return errors.Wrap(err, "accessing entity")
 		}
 
 		if err := walk.SignedEntity(ctx, se, func(ctx context.Context, se oci.SignedEntity) error {
 			// Get the digest for this entity in our walk.
 			d, err := se.(interface{ Digest() (v1.Hash, error) }).Digest()
 			if err != nil {
-				return err
+				return errors.Wrap(err, "computing digest")
 			}
 			digest := ref.Context().Digest(d.String())
 
 			err = signDigest(ctx, digest, staticPayload, ko, regOpts, annotations, upload, force, dd, sv, se)
 			if err != nil {
-				return err
+				return errors.Wrap(err, "signing digest")
 			}
 			return ErrDone
 		}); err != nil {
-			return err
+			return errors.Wrap(err, "recursively signing")
 		}
 	}
 
diff --git a/pkg/oci/file.go b/pkg/oci/file.go
index 5fc68cec16a..2d354ff9757 100644
--- a/pkg/oci/file.go
+++ b/pkg/oci/file.go
@@ -15,9 +15,16 @@
 
 package oci
 
+import "github.com/google/go-containerregistry/pkg/v1/types"
+
 // File is a degenerate form of SignedImage that stores a single file as a v1.Layer
 type File interface {
 	SignedImage
 
-	// TODO(mattmoor): Consider adding useful helpers.
+	// FileMediaType retrieves the media type of the File
+	FileMediaType() (types.MediaType, error)
+
+	// Payload fetches the opaque data that is being signed.
+	// This will always return data when there is no error.
+	Payload() ([]byte, error)
 }
diff --git a/pkg/oci/remote/image_test.go b/pkg/oci/remote/image_test.go
index 0854b1939ea..ba840f9a094 100644
--- a/pkg/oci/remote/image_test.go
+++ b/pkg/oci/remote/image_test.go
@@ -68,3 +68,40 @@ func TestSignedImage(t *testing.T) {
 		t.Errorf("len(Get()) = %d, wanted %d", got, wantLayers)
 	}
 }
+
+func TestSignedImageWithAttachment(t *testing.T) {
+	ri := remote.Image
+	t.Cleanup(func() {
+		remoteImage = ri
+	})
+	wantLayers := int64(1) // File must have a single layer
+
+	remoteImage = func(ref name.Reference, options ...remote.Option) (v1.Image, error) {
+		// Only called for signature images
+		return random.Image(300 /* byteSize */, wantLayers)
+	}
+
+	ref, err := name.ParseReference("gcr.io/distroless/static:nonroot")
+	if err != nil {
+		t.Fatalf("ParseRef() = %v", err)
+	}
+
+	si, err := SignedImage(ref)
+	if err != nil {
+		t.Fatalf("Signatures() = %v", err)
+	}
+
+	file, err := si.Attachment("sbom")
+	if err != nil {
+		t.Fatalf("Signatures() = %v", err)
+	}
+
+	payload, err := file.Payload()
+	if err != nil {
+		t.Errorf("Payload() = %v", err)
+	}
+	// We check greater than because it's wrapped in a tarball with `random.Layer`
+	if len(payload) < 300 {
+		t.Errorf("Payload() = %d bytes, wanted %d", len(payload), 300)
+	}
+}
diff --git a/pkg/oci/remote/remote.go b/pkg/oci/remote/remote.go
index 06bff3d17d2..ab4c63b77e8 100644
--- a/pkg/oci/remote/remote.go
+++ b/pkg/oci/remote/remote.go
@@ -17,6 +17,7 @@ package remote
 
 import (
 	"fmt"
+	"io"
 
 	"github.com/google/go-containerregistry/pkg/name"
 	v1 "github.com/google/go-containerregistry/pkg/v1"
@@ -154,5 +155,42 @@ func attachment(digestable digestable, attName string, o *options) (oci.File, er
 	if err != nil {
 		return nil, err
 	}
-	return oci.File(img), nil
+	ls, err := img.Layers()
+	if err != nil {
+		return nil, err
+	}
+	if len(ls) != 1 {
+		return nil, fmt.Errorf("expected exactly one layer in attachment, got %d", len(ls))
+	}
+
+	return &attache{
+		SignedImage: img,
+		layer:       ls[0],
+	}, nil
+}
+
+type attache struct {
+	oci.SignedImage
+	layer v1.Layer
+}
+
+var _ oci.File = (*attache)(nil)
+
+// FileMediaType implements oci.File
+func (f *attache) FileMediaType() (types.MediaType, error) {
+	return f.layer.MediaType()
+}
+
+// Payload implements oci.File
+func (f *attache) Payload() ([]byte, error) {
+	// remote layers are believed to be stored
+	// compressed, but we don't compress attachments
+	// so use "Compressed" to access the raw byte
+	// stream.
+	rc, err := f.layer.Compressed()
+	if err != nil {
+		return nil, err
+	}
+	defer rc.Close()
+	return io.ReadAll(rc)
 }
diff --git a/pkg/oci/static/file.go b/pkg/oci/static/file.go
index 7542af874db..270b5a6b763 100644
--- a/pkg/oci/static/file.go
+++ b/pkg/oci/static/file.go
@@ -16,6 +16,9 @@
 package static
 
 import (
+	"io"
+
+	v1 "github.com/google/go-containerregistry/pkg/v1"
 	"github.com/google/go-containerregistry/pkg/v1/empty"
 	"github.com/google/go-containerregistry/pkg/v1/mutate"
 	"github.com/google/go-containerregistry/pkg/v1/types"
@@ -31,14 +34,40 @@ func NewFile(payload []byte, opts ...Option) (oci.File, error) {
 	}
 	base := mutate.MediaType(empty.Image, types.OCIManifestSchema1)
 	base = mutate.ConfigMediaType(base, o.ConfigMediaType)
+	layer := &staticLayer{
+		b:    payload,
+		opts: o,
+	}
 	img, err := mutate.Append(base, mutate.Addendum{
-		Layer: &staticLayer{
-			b:    payload,
-			opts: o,
-		},
+		Layer: layer,
 	})
 	if err != nil {
 		return nil, err
 	}
-	return signed.Image(img), nil
+	return &file{
+		SignedImage: signed.Image(img),
+		layer:       layer,
+	}, nil
+}
+
+type file struct {
+	oci.SignedImage
+	layer v1.Layer
+}
+
+var _ oci.File = (*file)(nil)
+
+// FileMediaType implements oci.File
+func (f *file) FileMediaType() (types.MediaType, error) {
+	return f.layer.MediaType()
+}
+
+// Payload implements oci.File
+func (f *file) Payload() ([]byte, error) {
+	rc, err := f.layer.Uncompressed()
+	if err != nil {
+		return nil, err
+	}
+	defer rc.Close()
+	return io.ReadAll(rc)
 }
diff --git a/pkg/oci/static/file_test.go b/pkg/oci/static/file_test.go
index 4666ed06c08..8c074fbc7f8 100644
--- a/pkg/oci/static/file_test.go
+++ b/pkg/oci/static/file_test.go
@@ -27,12 +27,12 @@ import (
 
 func TestNewFile(t *testing.T) {
 	payload := "this is the content!"
-	img, err := NewFile([]byte(payload), WithLayerMediaType("foo"))
+	file, err := NewFile([]byte(payload), WithLayerMediaType("foo"))
 	if err != nil {
 		t.Fatalf("NewFile() = %v", err)
 	}
 
-	layers, err := img.Layers()
+	layers, err := file.Layers()
 	if err != nil {
 		t.Fatalf("Layers() = %v", err)
 	} else if got, want := len(layers), 1; got != want {
@@ -53,7 +53,7 @@ func TestNewFile(t *testing.T) {
 
 	t.Run("check media type", func(t *testing.T) {
 		wantMT := types.MediaType("foo")
-		gotMT, err := l.MediaType()
+		gotMT, err := file.FileMediaType()
 		if err != nil {
 			t.Fatalf("MediaType() = %v", err)
 		}
@@ -111,5 +111,13 @@ func TestNewFile(t *testing.T) {
 		if got, want := string(uncompContent), payload; got != want {
 			t.Errorf("Uncompressed() = %s, wanted %s", got, want)
 		}
+
+		gotPayload, err := file.Payload()
+		if err != nil {
+			t.Fatalf("Payload() = %v", err)
+		}
+		if got, want := string(gotPayload), payload; got != want {
+			t.Errorf("Payload() = %s, wanted %s", got, want)
+		}
 	})
 }
diff --git a/test/e2e_test.go b/test/e2e_test.go
index 36b41166f81..3c77e1047e2 100644
--- a/test/e2e_test.go
+++ b/test/e2e_test.go
@@ -622,7 +622,7 @@ func TestAttachSBOM(t *testing.T) {
 	if err == nil {
 		t.Fatal("Expected error")
 	}
-	t.Log(out)
+	t.Log(out.String())
 	out.Reset()
 
 	// Upload it!
@@ -632,7 +632,7 @@ func TestAttachSBOM(t *testing.T) {
 	if err != nil {
 		t.Fatal(err)
 	}
-	t.Log(out)
+	t.Log(out.String())
 	if len(sboms) != 1 {
 		t.Fatalf("Expected one sbom, got %d", len(sboms))
 	}