diff --git a/hscontrol/policy/v2/sshtester_compat_test.go b/hscontrol/policy/v2/sshtester_compat_test.go
new file mode 100644
index 00000000..3c3057d9
--- /dev/null
+++ b/hscontrol/policy/v2/sshtester_compat_test.go
@@ -0,0 +1,97 @@
+// Compatibility tests for the policy `sshTests` block, replaying captures
+// recorded against a real Tailscale SaaS tailnet. The runner mirrors the
+// pattern in policytester_compat_test.go: a single Glob over a testdata
+// directory, one t.Run per file. Each capture is one of:
+//
+//   - APIResponseCode != 200 — the policy was rejected by SaaS, the
+//     captured Message is the body the user saw, and headscale must
+//     reject the same input with an error string that contains the same
+//     body (substring match, allowing wrapping like "test(s) failed:\n…").
+//   - APIResponseCode == 200 — SaaS accepted the policy (its sshTests
+//     block passed); headscale's evaluateSSHTests must also pass.
+//
+// Captures live in testdata/sshtest_results/*.hujson. Scenarios in
+// knownSSHTesterDivergences are skipped with their tracking note —
+// these are real Tailscale ↔ headscale divergences that need engine-level
+// fixes in follow-up PRs.
+//
+// Source format: github.com/juanfont/headscale/hscontrol/types/testcapture
+
+package v2
+
+import (
+	"path/filepath"
+	"strings"
+	"testing"
+
+	"github.com/juanfont/headscale/hscontrol/types/testcapture"
+	"github.com/stretchr/testify/require"
+)
+
+// knownSSHTesterDivergences tracks scenarios where headscale and SaaS
+// disagree on whether a policy is accepted. Empty until captures land
+// and any genuine engine bugs are uncovered.
+var knownSSHTesterDivergences = map[string]string{}
+
+func TestSSHTesterCompat(t *testing.T) {
+	t.Parallel()
+
+	files, err := filepath.Glob(filepath.Join("testdata", "sshtest_results", "*.hujson"))
+	require.NoError(t, err, "failed to glob test files")
+
+	if len(files) == 0 {
+		t.Skip("no sshtest captures yet")
+	}
+
+	users := setupSSHDataCompatUsers()
+	nodes := setupSSHDataCompatNodes(users)
+
+	for _, file := range files {
+		c, err := testcapture.Read(file)
+		require.NoError(t, err, "reading %s", file)
+
+		t.Run(c.TestID, func(t *testing.T) {
+			t.Parallel()
+
+			if reason, skip := knownSSHTesterDivergences[c.TestID]; skip {
+				t.Skip(reason)
+			}
+
+			policyJSON := []byte(c.Input.FullPolicy)
+
+			pm, parseErr := NewPolicyManager(policyJSON, users, nodes.ViewSlice())
+
+			if c.Input.APIResponseCode == 200 {
+				require.NoError(t, parseErr,
+					"tailscale accepted this policy; headscale must parse it")
+
+				_, setErr := pm.SetPolicy(policyJSON)
+				require.NoError(t, setErr,
+					"tailscale accepted this policy; headscale sshTests must pass")
+
+				return
+			}
+
+			var got error
+
+			switch {
+			case parseErr != nil:
+				got = parseErr
+			default:
+				_, setErr := pm.SetPolicy(policyJSON)
+				got = setErr
+			}
+
+			require.Error(t, got, "tailscale rejected; headscale must reject too")
+
+			if c.Input.APIResponseBody == nil || c.Input.APIResponseBody.Message == "" {
+				return
+			}
+
+			want := c.Input.APIResponseBody.Message
+			if !strings.Contains(got.Error(), want) {
+				t.Errorf("error body mismatch\n  tailscale wants: %q\n  headscale got:   %q", want, got.Error())
+			}
+		})
+	}
+}