diff --git a/pkg/v1/remote/error_roundtrip_test.go b/pkg/v1/remote/error_roundtrip_test.go
index 981f8fc97..6425bb386 100644
--- a/pkg/v1/remote/error_roundtrip_test.go
+++ b/pkg/v1/remote/error_roundtrip_test.go
@@ -125,3 +125,52 @@ func TestBlobStatusCodeReturned(t *testing.T) {
 		t.Errorf("Incorrect status code received, got %v, wanted %v", terr.StatusCode, http.StatusTeapot)
 	}
 }
+
+func TestRetryPreservesStructuredErrors(t *testing.T) {
+	// Test that structured registry errors are preserved when retries are enabled
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if r.URL.Path == "/v2/" {
+			return
+		}
+		// Return a structured registry error
+		w.Header().Set("Content-Type", "application/json")
+		w.WriteHeader(http.StatusNotFound)
+		w.Write([]byte(`{"errors":[{"code":"MANIFEST_UNKNOWN","message":"manifest unknown","detail":"unknown tag=v1.0.0"}]}`))
+	})
+
+	server := httptest.NewServer(handler)
+	defer server.Close()
+
+	ref, err := name.NewTag(strings.TrimPrefix(server.URL+"/test:v1.0.0", "http://"))
+	if err != nil {
+		t.Fatalf("Unable to parse tag: %v", err)
+	}
+
+	// Test without retry - should get structured error
+	_, err = remote.Image(ref)
+	if err == nil {
+		t.Fatal("Expected error, got nil")
+	}
+	withoutRetryMsg := err.Error()
+
+	// Test with retry - should still get structured error (not generic 404)
+	_, err = remote.Image(ref, remote.WithRetryStatusCodes(http.StatusNotFound))
+	if err == nil {
+		t.Fatal("Expected error, got nil")
+	}
+	withRetryMsg := err.Error()
+
+	// Both should contain the structured error message
+	expectedSubstring := "MANIFEST_UNKNOWN: manifest unknown; unknown tag=v1.0.0"
+	if !strings.Contains(withoutRetryMsg, expectedSubstring) {
+		t.Errorf("Without retry error %q should contain %q", withoutRetryMsg, expectedSubstring)
+	}
+	if !strings.Contains(withRetryMsg, expectedSubstring) {
+		t.Errorf("With retry error %q should contain %q", withRetryMsg, expectedSubstring)
+	}
+
+	// The retry case should NOT contain generic "unexpected status code 404"
+	if strings.Contains(withRetryMsg, "unexpected status code 404 Not Found") {
+		t.Errorf("With retry error should not contain generic 404 message, got: %q", withRetryMsg)
+	}
+}
diff --git a/pkg/v1/remote/transport/error.go b/pkg/v1/remote/transport/error.go
index 482a4adee..91f72de59 100644
--- a/pkg/v1/remote/transport/error.go
+++ b/pkg/v1/remote/transport/error.go
@@ -15,6 +15,7 @@
 package transport
 
 import (
+	"bytes"
 	"encoding/json"
 	"fmt"
 	"io"
@@ -189,6 +190,8 @@ func retryError(resp *http.Response) error {
 	if err != nil {
 		return err
 	}
+	_ = resp.Body.Close()
+	resp.Body = io.NopCloser(bytes.NewReader(b))
 
 	rerr := makeError(resp, b)
 	rerr.temporary = true
diff --git a/pkg/v1/remote/transport/error_test.go b/pkg/v1/remote/transport/error_test.go
index 679b6e1a8..310deb741 100644
--- a/pkg/v1/remote/transport/error_test.go
+++ b/pkg/v1/remote/transport/error_test.go
@@ -234,3 +234,85 @@ func (e *errReadCloser) Read(_ []byte) (int, error) {
 func (e *errReadCloser) Close() error {
 	return e.err
 }
+
+func TestRetryError(t *testing.T) {
+	tests := []struct {
+		name      string
+		status    int
+		body      string
+		wantError string
+	}{
+		{
+			name:      "returned error",
+			status:    http.StatusInternalServerError,
+			body:      "boom",
+			wantError: "unexpected status code 500 Internal Server Error: boom",
+		},
+		{
+			name:      "empty body",
+			status:    http.StatusInternalServerError,
+			body:      "",
+			wantError: "unexpected status code 500 Internal Server Error",
+		},
+	}
+
+	for _, test := range tests {
+		t.Run(test.name, func(t *testing.T) {
+			resp := &http.Response{
+				StatusCode: test.status,
+				Body:       io.NopCloser(bytes.NewBufferString(test.body)),
+			}
+
+			// Call retryError
+			err := retryError(resp)
+			if err == nil {
+				t.Fatal("retryError() = nil, wanted error")
+			}
+
+			// Verify the error is marked as temporary
+			var terr *Error
+			if !errors.As(err, &terr) {
+				t.Fatalf("retryError() = %T, wanted *Error", err)
+			}
+			if !terr.Temporary() {
+				t.Error("retryError() should return temporary error")
+			}
+
+			// Verify error message
+			if terr.Error() != test.wantError {
+				t.Errorf("retryError().Error() = %q, want %q", terr.Error(), test.wantError)
+			}
+
+			// Verify the response body can still be read
+			body, err := io.ReadAll(resp.Body)
+			if err != nil {
+				t.Fatalf("Failed to read response body after retryError: %v", err)
+			}
+			if string(body) != test.body {
+				t.Errorf("Response body after retryError = %q, want %q", string(body), test.body)
+			}
+
+			// Verify we can read it again (body should be rewindable)
+			body2, err := io.ReadAll(resp.Body)
+			if err != nil {
+				t.Fatalf("Failed to read response body second time: %v", err)
+			}
+			if string(body2) != "" {
+				t.Errorf("Second read should be empty, got %q", string(body2))
+			}
+		})
+	}
+}
+
+func TestRetryErrorReadError(t *testing.T) {
+	expectedErr := errors.New("read error")
+	resp := &http.Response{
+		StatusCode: http.StatusInternalServerError,
+		Body:       &errReadCloser{expectedErr},
+	}
+
+	err := retryError(resp)
+	if !errors.Is(err, expectedErr) {
+		t.Errorf("retryError() = %v, want %v", err, expectedErr)
+	}
+}