diff --git a/internal/autostart/autostart_windows.go b/internal/autostart/autostart_windows.go
index 20ac6c7..d621c16 100644
--- a/internal/autostart/autostart_windows.go
+++ b/internal/autostart/autostart_windows.go
@@ -13,7 +13,9 @@
 package autostart
 
 import (
+	"errors"
 	"fmt"
+	"io/fs"
 	"os"
 	"path/filepath"
 	"strings"
@@ -42,7 +44,13 @@ func Enable(skrogExe string) error {
 			"(a console binary at logon would flash a console window): %w", err)
 	}
 
-	k, err := registry.OpenKey(registry.CURRENT_USER, runKeyPath, registry.SET_VALUE)
+	// CreateKey, not OpenKey: the Run key is created on demand by Windows and
+	// is NOT guaranteed to exist (#444). A profile that has never had a logon
+	// entry has no key, and OpenKey then fails with "The system cannot find
+	// the file specified" — which reads as a missing FILE and sends the user
+	// looking for skrogw.exe. CreateKey opens an existing key unchanged, so
+	// this costs nothing on the machines that already have one.
+	k, _, err := registry.CreateKey(registry.CURRENT_USER, runKeyPath, registry.SET_VALUE)
 	if err != nil {
 		return fmt.Errorf("opening the Run key: %w", err)
 	}
@@ -59,6 +67,13 @@ func Enable(skrogExe string) error {
 // success: the user asked for a state, not an action.
 func Disable() error {
 	k, err := registry.OpenKey(registry.CURRENT_USER, runKeyPath, registry.SET_VALUE)
+	if errors.Is(err, registry.ErrNotExist) || errors.Is(err, fs.ErrNotExist) {
+		// No Run key at all, so nothing is registered — which is the state
+		// the caller asked for. The comment above already said a missing
+		// VALUE is success; a missing KEY is the same answer one level up,
+		// and failing here contradicted it (#444).
+		return nil
+	}
 	if err != nil {
 		return fmt.Errorf("opening the Run key: %w", err)
 	}
@@ -106,6 +121,13 @@ func DisableIfOwned(installDir string) (bool, error) {
 // Status returns whether autostart is registered, and the command if so.
 func Status() (enabled bool, command string, err error) {
 	k, err := registry.OpenKey(registry.CURRENT_USER, runKeyPath, registry.QUERY_VALUE)
+	if errors.Is(err, registry.ErrNotExist) || errors.Is(err, fs.ErrNotExist) {
+		// No key means nothing is registered, which is an answer and not a
+		// failure (#444). Reporting an error here made `skrog status` and
+		// `doctor` fail on a profile that had simply never autostarted
+		// anything.
+		return false, "", nil
+	}
 	if err != nil {
 		return false, "", fmt.Errorf("opening the Run key: %w", err)
 	}
diff --git a/internal/autostart/autostart_windows_test.go b/internal/autostart/autostart_windows_test.go
index efbb24a..9837bb6 100644
--- a/internal/autostart/autostart_windows_test.go
+++ b/internal/autostart/autostart_windows_test.go
@@ -194,3 +194,85 @@ func TestDisableIfOwnedMatchesAResolvedDir(t *testing.T) {
 		t.Fatal("the owner could not remove its own entry when passing a resolved directory")
 	}
 }
+
+// useAbsentScratchKey points the package at a key that does NOT exist, and
+// makes sure it stays that way until the code under test creates it.
+//
+// This is the case the existing helper cannot cover, because it creates the
+// key first — with a comment saying it must exist for OpenKey(SET_VALUE) to
+// succeed. That comment is the bug report: the product assumed a precondition
+// the test then supplied for it (#444).
+func useAbsentScratchKey(t *testing.T) {
+	t.Helper()
+	orig := runKeyPath
+	runKeyPath = `Software\SkrogTest\AbsentRun`
+
+	// Make sure a previous run did not leave it behind.
+	registry.DeleteKey(registry.CURRENT_USER, runKeyPath)
+	if k, err := registry.OpenKey(registry.CURRENT_USER, runKeyPath, registry.QUERY_VALUE); err == nil {
+		k.Close()
+		t.Fatalf("%s exists; this test is about the case where it does not", runKeyPath)
+	}
+
+	t.Cleanup(func() {
+		registry.DeleteKey(registry.CURRENT_USER, runKeyPath)
+		registry.DeleteKey(registry.CURRENT_USER, `Software\SkrogTest`)
+		runKeyPath = orig
+	})
+}
+
+// A profile with no Run key at all must still be able to enable autostart.
+//
+// Windows creates HKCU\...\CurrentVersion\Run on demand, so a profile that has
+// never registered a logon entry does not have one. OpenKey then fails with
+// "The system cannot find the file specified", which `skrog install --config`
+// surfaced as:
+//
+//	skrog: applying config: opening the Run key: The system cannot find the file specified.
+//
+// — a message that reads as a missing FILE and sends the user looking for
+// skrogw.exe. Found by the nightly acceptance run on a clean hosted runner.
+func TestEnableCreatesTheRunKeyWhenAbsent(t *testing.T) {
+	useAbsentScratchKey(t)
+	exe := fakeInstall(t, true)
+
+	if err := Enable(exe); err != nil {
+		t.Fatalf("Enable with no Run key: %v", err)
+	}
+	enabled, cmd, err := Status()
+	if err != nil {
+		t.Fatalf("Status: %v", err)
+	}
+	if !enabled {
+		t.Error("autostart not registered after Enable created the key")
+	}
+	if !strings.Contains(cmd, "skrogw.exe") {
+		t.Errorf("Run entry = %q, want the skrogw launcher", cmd)
+	}
+}
+
+// Status on a profile with no Run key is "not enabled", not an error. It used
+// to fail, which broke `skrog status` and `doctor` on such a profile.
+func TestStatusWithNoRunKeyIsNotAnError(t *testing.T) {
+	useAbsentScratchKey(t)
+
+	enabled, cmd, err := Status()
+	if err != nil {
+		t.Fatalf("Status with no Run key returned an error: %v", err)
+	}
+	if enabled || cmd != "" {
+		t.Errorf("Status = (%v, %q), want (false, \"\")", enabled, cmd)
+	}
+}
+
+// Disable's own doc comment says removing an entry that does not exist is
+// success — "the user asked for a state, not an action". That held for a
+// missing VALUE and not for a missing KEY, which is the same answer one level
+// up.
+func TestDisableWithNoRunKeyIsSuccess(t *testing.T) {
+	useAbsentScratchKey(t)
+
+	if err := Disable(); err != nil {
+		t.Errorf("Disable with no Run key: %v", err)
+	}
+}