diff --git a/pkg/securitypolicy/securitypolicy_options.go b/pkg/securitypolicy/securitypolicy_options.go
index 12f28428b8..c0d87a0fee 100644
--- a/pkg/securitypolicy/securitypolicy_options.go
+++ b/pkg/securitypolicy/securitypolicy_options.go
@@ -461,7 +461,12 @@ func (s *SecurityOptions) WriteSecurityContextDir(spec *specs.Spec) (string, err
 		platformReferenceInfoBase64 = base64.StdEncoding.EncodeToString(s.platformReferenceInfo)
 	}
 	s.platformReferenceInfoMutex.RUnlock()
-	hostAMDCert := spec.Annotations[annotations.WCOWHostAMDCertificate]
+	// HostAMDCertificate is a deprecated alias of the LCOW key. Prefer that
+	// key, but preserve support for callers that supply the WCOW key.
+	hostAMDCert := spec.Annotations[annotations.LCOWHostAMDCertificate]
+	if hostAMDCert == "" {
+		hostAMDCert = spec.Annotations[annotations.WCOWHostAMDCertificate]
+	}
 	if len(encodedPolicy) > 0 || len(hostAMDCert) > 0 || len(s.UvmReferenceInfo) > 0 || len(s.UvmHashEnvelopeReferenceInfo) > 0 || len(tcbReferenceInfoBase64) > 0 || len(platformReferenceInfoBase64) > 0 {
 		// Use os.MkdirTemp to make sure that the directory is unique.
 		securityContextDir, err := os.MkdirTemp(spec.Root.Path, SecurityContextDirTemplate)
diff --git a/pkg/securitypolicy/securitypolicy_options_test.go b/pkg/securitypolicy/securitypolicy_options_test.go
new file mode 100644
index 0000000000..c17896dad2
--- /dev/null
+++ b/pkg/securitypolicy/securitypolicy_options_test.go
@@ -0,0 +1,140 @@
+package securitypolicy
+
+import (
+	"encoding/base64"
+	"os"
+	"path/filepath"
+	"reflect"
+	"testing"
+
+	"github.com/Microsoft/hcsshim/pkg/annotations"
+	"github.com/opencontainers/runtime-spec/specs-go"
+)
+
+func TestWriteSecurityContextDirAMDCertificate(t *testing.T) {
+	const lcowCert = "bGNvdy1jZXJ0"
+	const wcowCert = "d2Nvdy1jZXJ0"
+	for _, tc := range []struct {
+		name        string
+		annotations map[string]string
+		wantCert    string
+	}{
+		{
+			name:        "LCOW",
+			annotations: map[string]string{annotations.LCOWHostAMDCertificate: lcowCert},
+			wantCert:    lcowCert,
+		},
+		{
+			name:        "deprecated generic alias",
+			annotations: map[string]string{annotations.HostAMDCertificate: lcowCert}, //nolint:staticcheck // SA1019: intentionally test compatibility with the deprecated alias.
+			wantCert:    lcowCert,
+		},
+		{
+			name:        "WCOW fallback",
+			annotations: map[string]string{annotations.WCOWHostAMDCertificate: wcowCert},
+			wantCert:    wcowCert,
+		},
+		{
+			name: "LCOW takes precedence",
+			annotations: map[string]string{
+				annotations.LCOWHostAMDCertificate: lcowCert,
+				annotations.WCOWHostAMDCertificate: wcowCert,
+			},
+			wantCert: lcowCert,
+		},
+		{
+			name: "empty LCOW falls back to WCOW",
+			annotations: map[string]string{
+				annotations.LCOWHostAMDCertificate: "",
+				annotations.WCOWHostAMDCertificate: wcowCert,
+			},
+			wantCert: wcowCert,
+		},
+		{name: "nil annotations"},
+		{name: "empty annotations", annotations: map[string]string{}},
+		{
+			name: "empty certificates",
+			annotations: map[string]string{
+				annotations.LCOWHostAMDCertificate: "",
+				annotations.WCOWHostAMDCertificate: "",
+			},
+		},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			for _, withOtherContext := range []bool{false, true} {
+				name := "certificate only"
+				if withOtherContext {
+					name = "with other security context"
+				}
+				t.Run(name, func(t *testing.T) {
+					root := t.TempDir()
+					spec := &specs.Spec{
+						Root:        &specs.Root{Path: root},
+						Process:     &specs.Process{Env: []string{"EXISTING=value"}},
+						Annotations: tc.annotations,
+					}
+					enforcer := &OpenDoorSecurityPolicyEnforcer{}
+					options := &SecurityOptions{PolicyEnforcer: enforcer}
+					wantFiles := map[string]string{}
+					if tc.wantCert != "" {
+						wantFiles[HostAMDCertFilename] = tc.wantCert
+					}
+					if withOtherContext {
+						enforcer.encodedSecurityPolicy = "cG9saWN5"
+						options.UvmReferenceInfo = "cmVmZXJlbmNl"
+						options.UvmHashEnvelopeReferenceInfo = "aGFzaC1lbnZlbG9wZQ=="
+						options.tcbReferenceInfo = []byte("tcb")
+						options.platformReferenceInfo = []byte("platform")
+						wantFiles[PolicyFilename] = enforcer.encodedSecurityPolicy
+						wantFiles[ReferenceInfoFilename] = options.UvmReferenceInfo
+						wantFiles[HashEnvelopeReferenceInfoFilename] = options.UvmHashEnvelopeReferenceInfo
+						wantFiles[TCBReferenceInfoFilename] = base64.StdEncoding.EncodeToString(options.tcbReferenceInfo)
+						wantFiles[PlatformReferenceInfoFilename] = base64.StdEncoding.EncodeToString(options.platformReferenceInfo)
+					}
+
+					dir, err := options.WriteSecurityContextDir(spec)
+					if err != nil {
+						t.Fatal(err)
+					}
+					wantEnv := []string{"EXISTING=value"}
+					if len(wantFiles) == 0 {
+						if dir != "" {
+							t.Fatalf("unexpected security context directory %q", dir)
+						}
+						entries, err := os.ReadDir(root)
+						if err != nil {
+							t.Fatal(err)
+						}
+						if len(entries) != 0 {
+							t.Fatalf("unexpected rootfs entries: %v", entries)
+						}
+					} else {
+						if dir == "" || filepath.Dir(dir) != root {
+							t.Fatalf("expected security context directory under %q, got %q", root, dir)
+						}
+						entries, err := os.ReadDir(dir)
+						if err != nil {
+							t.Fatal(err)
+						}
+						if len(entries) != len(wantFiles) {
+							t.Fatalf("expected %d context files, got %d", len(wantFiles), len(entries))
+						}
+						for filename, want := range wantFiles {
+							got, err := os.ReadFile(filepath.Join(dir, filename))
+							if err != nil {
+								t.Fatal(err)
+							}
+							if string(got) != want {
+								t.Errorf("%s: got %q, want %q", filename, got, want)
+							}
+						}
+						wantEnv = append(wantEnv, "UVM_SECURITY_CONTEXT_DIR=/"+filepath.Base(dir))
+					}
+					if !reflect.DeepEqual(spec.Process.Env, wantEnv) {
+						t.Errorf("environment: got %v, want %v", spec.Process.Env, wantEnv)
+					}
+				})
+			}
+		})
+	}
+}