diff --git a/internal/tools/sandbox_denial.go b/internal/tools/sandbox_denial.go
index 72ddc58d..2431ea5d 100644
--- a/internal/tools/sandbox_denial.go
+++ b/internal/tools/sandbox_denial.go
@@ -66,9 +66,36 @@ func sandboxDenialKind(plan zeroSandbox.CommandPlan, exitCode int, sections ...s
 	if plan.TargetBackend == zeroSandbox.BackendLinuxBwrap && exitCode == 128+31 {
 		return SandboxDenialKindSandbox, "seccomp"
 	}
+	// Windows restricted-token failures are often SILENT: a spawn the token
+	// cannot satisfy (executable or DLL unreadable under the restricted-SID
+	// check, MSYS runtime init death, loader status 0xC0000135/0xC0000142)
+	// produces a nonzero exit with no output at all, so none of the keyword
+	// heuristics above can ever fire. Treat "wrapped Windows command failed
+	// without writing a single byte" as a likely sandbox denial so the caller
+	// offers the unsandboxed-retry prompt instead of surfacing a bare
+	// "command completed with no output". A command that legitimately fails
+	// silently (findstr with no match, for one) costs one extra approval
+	// prompt; the inverse misclassification silently strands the whole
+	// session, so the trade goes to prompting.
+	if windowsWrappedBackend(plan.TargetBackend) && sectionsEmpty(sections...) {
+		return SandboxDenialKindSandbox, "no output from sandboxed command"
+	}
 	return "", ""
 }
 
+func windowsWrappedBackend(backend zeroSandbox.BackendName) bool {
+	return backend == zeroSandbox.BackendWindowsRestrictedToken || backend == zeroSandbox.BackendWindowsElevated
+}
+
+func sectionsEmpty(sections ...string) bool {
+	for _, section := range sections {
+		if strings.TrimSpace(section) != "" {
+			return false
+		}
+	}
+	return true
+}
+
 func networkDeniedBySandbox(plan zeroSandbox.CommandPlan) bool {
 	return plan.PermissionProfile.Network.Mode == zeroSandbox.NetworkDeny || plan.Policy.Network == zeroSandbox.NetworkDeny
 }
diff --git a/internal/tools/sandbox_denial_test.go b/internal/tools/sandbox_denial_test.go
index e71bd8a1..f9dbbbdd 100644
--- a/internal/tools/sandbox_denial_test.go
+++ b/internal/tools/sandbox_denial_test.go
@@ -42,3 +42,53 @@ func TestLikelySandboxDeniedIgnoresUnsandboxedFailure(t *testing.T) {
 		t.Fatal("unsandboxed command output must not be classified as a sandbox denial")
 	}
 }
+
+func TestLikelySandboxDeniedDetectsSilentWindowsWrappedFailure(t *testing.T) {
+	for _, backend := range []zeroSandbox.BackendName{
+		zeroSandbox.BackendWindowsRestrictedToken,
+		zeroSandbox.BackendWindowsElevated,
+	} {
+		plan := zeroSandbox.CommandPlan{
+			Wrapped:       true,
+			TargetBackend: backend,
+		}
+		if !likelySandboxDenied(plan, 1, "", "  \n") {
+			t.Fatalf("wrapped Windows command failing with empty output must be classified as sandbox denied (backend %s)", backend)
+		}
+		meta := map[string]string{}
+		markLikelySandboxDenial(meta, plan, 1, "")
+		if meta[SandboxLikelyDeniedMeta] != "true" || meta[SandboxDenialKindMeta] != SandboxDenialKindSandbox {
+			t.Fatalf("silent windows denial meta = %#v (backend %s)", meta, backend)
+		}
+	}
+}
+
+func TestLikelySandboxDeniedIgnoresSilentWindowsWrappedSuccess(t *testing.T) {
+	plan := zeroSandbox.CommandPlan{
+		Wrapped:       true,
+		TargetBackend: zeroSandbox.BackendWindowsRestrictedToken,
+	}
+	if likelySandboxDenied(plan, 0, "") {
+		t.Fatal("wrapped Windows command exiting 0 with empty output must not be classified as sandbox denied")
+	}
+}
+
+func TestLikelySandboxDeniedIgnoresSilentFailureOnOtherBackends(t *testing.T) {
+	plan := zeroSandbox.CommandPlan{
+		Wrapped:       true,
+		TargetBackend: zeroSandbox.BackendLinuxBwrap,
+	}
+	if likelySandboxDenied(plan, 1, "") {
+		t.Fatal("silent nonzero exit on non-Windows backends must not be classified as sandbox denied")
+	}
+}
+
+func TestLikelySandboxDeniedIgnoresSilentWindowsFailureWithOutput(t *testing.T) {
+	plan := zeroSandbox.CommandPlan{
+		Wrapped:       true,
+		TargetBackend: zeroSandbox.BackendWindowsRestrictedToken,
+	}
+	if likelySandboxDenied(plan, 1, "fatal: not a git repository") {
+		t.Fatal("a wrapped Windows command that produced unrelated output must not be classified as sandbox denied")
+	}
+}