diff --git a/internal/shellwrap/shellwrap.go b/internal/shellwrap/shellwrap.go
index f41681240..d7d6bbdc7 100644
--- a/internal/shellwrap/shellwrap.go
+++ b/internal/shellwrap/shellwrap.go
@@ -217,15 +217,27 @@ func ResolveDockerPath(logger *zap.Logger) (string, error) {
 	dockerPathMu.Lock()
 	defer dockerPathMu.Unlock()
 
-	// Honor cache: keep successful resolutions forever; treat failures as
-	// retryable after dockerPathNegativeTTL.
-	if dockerPathHasResult {
-		if dockerPathErr == nil {
-			return dockerPath, nil
-		}
-		if !dockerPathExpires.IsZero() && time.Now().Before(dockerPathExpires) {
-			return dockerPath, dockerPathErr
+	// Honor cache: keep successful resolutions forever.
+	if dockerPathHasResult && dockerPathErr == nil {
+		return dockerPath, nil
+	}
+
+	// A cached negative within its TTL would normally short-circuit here. But
+	// the well-known-path probe is a pure os.Stat — never sandbox- or
+	// login-shell-restricted — so a negative cached because only the restricted
+	// login-shell leg failed must NOT permanently shadow a docker binary that is
+	// sitting at a well-known path right now (the spawn-vs-status divergence in
+	// MCP-2744). Re-run the cheap probe before honoring a live negative; on
+	// success, upgrade the cache to a permanent success and return it.
+	if dockerPathHasResult && dockerPathErr != nil &&
+		!dockerPathExpires.IsZero() && time.Now().Before(dockerPathExpires) {
+		if p := probeWellKnownDocker(logger); p != "" {
+			dockerPath = p
+			dockerPathErr = nil
+			dockerPathExpires = time.Time{}
+			return p, nil
 		}
+		return dockerPath, dockerPathErr
 	}
 
 	path, err := resolveDockerPathUncached(logger)
diff --git a/internal/shellwrap/shellwrap_test.go b/internal/shellwrap/shellwrap_test.go
index dd2d0e6a6..a05af95c8 100644
--- a/internal/shellwrap/shellwrap_test.go
+++ b/internal/shellwrap/shellwrap_test.go
@@ -219,6 +219,51 @@ func TestResolveDockerPath_NegativeTTLRetry(t *testing.T) {
 	assert.Equal(t, want, got)
 }
 
+// TestResolveDockerPath_StatProbeOverridesLiveNegative is the MCP-2744
+// regression guard: a still-LIVE cached negative (within its TTL, NOT expired)
+// must never shadow a docker binary that is sitting at a well-known path right
+// now. The well-known-path probe is a pure os.Stat — it is never sandbox- or
+// login-shell-restricted — so the first resolution failing only because the
+// restricted login-shell leg failed must not poison discovery for the whole
+// TTL window. Distinct from TestResolveDockerPath_NegativeTTLRetry, which
+// relies on TTL expiry; here the TTL stays at its default so the negative is
+// still "live" on the second call.
+func TestResolveDockerPath_StatProbeOverridesLiveNegative(t *testing.T) {
+	if runtime.GOOS == "windows" {
+		t.Skip("unix-only fixture")
+	}
+	resetDockerPathCacheForTest()
+	t.Cleanup(resetDockerPathCacheForTest)
+
+	// Leave dockerPathNegativeTTL at its default (60s) so the cached negative is
+	// still valid on the second call — we prove the os.Stat probe overrides it.
+
+	// FIRST call fails everywhere: no PATH docker, no well-known docker, the
+	// login shell emits nothing.
+	prevPaths := wellKnownDockerPathsFn
+	wellKnownDockerPathsFn = func() []string { return nil }
+	t.Cleanup(func() { wellKnownDockerPathsFn = prevPaths })
+
+	t.Setenv("PATH", t.TempDir())
+	shellDir := t.TempDir()
+	fakeShell := writeFakeShell(t, shellDir, "")
+	t.Setenv("SHELL", fakeShell)
+
+	_, err := ResolveDockerPath(nil)
+	require.Error(t, err, "first call should cache a negative (docker absent everywhere)")
+
+	// Docker Desktop's bundle binary now appears at a well-known path. The cheap
+	// os.Stat probe must override the still-live cached negative on the very
+	// next call — no TTL expiry required.
+	dockerDir := t.TempDir()
+	want := writeFakeDocker(t, dockerDir)
+	wellKnownDockerPathsFn = func() []string { return []string{want} }
+
+	got, err := ResolveDockerPath(nil)
+	require.NoError(t, err, "a live negative must not shadow a now-present well-known docker")
+	assert.Equal(t, want, got)
+}
+
 // TestResolveDockerPath_WellKnownPathFallback simulates a PKG-installer
 // context: docker is missing from $PATH and the login shell emits nothing,
 // but Docker Desktop installed a binary at a well-known path. The fallback