diff --git a/CHANGELOG.md b/CHANGELOG.md
index 96963b3..dc8fbe2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## 0.11.6 - Unreleased
 
+### Fixes
+
+- Show setup guidance instead of a raw missing-file error when configuration-dependent commands cannot find `config.toml`. Thanks @0xdevalias.
+
 ## 0.11.5 - 2026-07-09
 
 ### Maintenance
diff --git a/internal/cli/cli.go b/internal/cli/cli.go
index d2636e5..0ef849e 100644
--- a/internal/cli/cli.go
+++ b/internal/cli/cli.go
@@ -554,6 +554,9 @@ func (r *runtime) withMessagesSyncServices(fn func() error) error {
 func (r *runtime) withServicesUpdateLockedOperation(withDiscord bool, updateMode shareUpdateMode, lockDB bool, operation string, fn func() error) error {
 	cfg, err := config.Load(r.configPath)
 	if err != nil {
+		if errors.Is(err, os.ErrNotExist) {
+			return configErr(fmt.Errorf("config file not found at %s; run `discrawl init`, pass `--config <path>`, or set %s", r.configPath, config.DefaultConfigEnv))
+		}
 		return configErr(err)
 	}
 	if err := config.EnsureRuntimeDirs(cfg); err != nil {
diff --git a/internal/cli/cli_test.go b/internal/cli/cli_test.go
index a005248..cb6dfde 100644
--- a/internal/cli/cli_test.go
+++ b/internal/cli/cli_test.go
@@ -4503,9 +4503,21 @@ func TestPrintJSONAndPlain(t *testing.T) {
 func TestWithServicesErrors(t *testing.T) {
 	t.Parallel()
 
-	rt := &runtime{ctx: context.Background(), configPath: filepath.Join(t.TempDir(), "missing.toml"), stdout: &bytes.Buffer{}, stderr: &bytes.Buffer{}}
+	missingPath := filepath.Join(t.TempDir(), "missing.toml")
+	rt := &runtime{ctx: context.Background(), configPath: missingPath, stdout: &bytes.Buffer{}, stderr: &bytes.Buffer{}}
 	err := rt.withServices(false, func() error { return nil })
 	require.Equal(t, 3, ExitCode(err))
+	require.ErrorContains(t, err, missingPath)
+	require.ErrorContains(t, err, "discrawl init")
+	require.ErrorContains(t, err, "--config")
+	require.ErrorContains(t, err, config.DefaultConfigEnv)
+
+	invalidPath := filepath.Join(t.TempDir(), "invalid.toml")
+	require.NoError(t, os.WriteFile(invalidPath, []byte("invalid = ["), 0o600))
+	rt = &runtime{ctx: context.Background(), configPath: invalidPath, stdout: &bytes.Buffer{}, stderr: &bytes.Buffer{}}
+	err = rt.withServices(false, func() error { return nil })
+	require.Equal(t, 3, ExitCode(err))
+	require.NotContains(t, err.Error(), "discrawl init")
 
 	cfgPath := filepath.Join(t.TempDir(), "config.toml")
 	cfg := config.Default()
@@ -4535,6 +4547,24 @@ func TestWithServicesErrors(t *testing.T) {
 	require.Equal(t, 4, ExitCode(err))
 }
 
+func TestTailMissingConfigGuidance(t *testing.T) {
+	home := t.TempDir()
+	configHome := filepath.Join(home, "config")
+	t.Setenv("HOME", home)
+	t.Setenv("XDG_CONFIG_HOME", configHome)
+	t.Setenv("XDG_DATA_HOME", filepath.Join(home, "data"))
+	t.Setenv("XDG_CACHE_HOME", filepath.Join(home, "cache"))
+	t.Setenv("XDG_STATE_HOME", filepath.Join(home, "state"))
+	t.Setenv(config.DefaultConfigEnv, "")
+
+	err := Run(context.Background(), []string{"tail"}, &bytes.Buffer{}, &bytes.Buffer{})
+	require.Equal(t, 3, ExitCode(err))
+	require.ErrorContains(t, err, filepath.Join(configHome, "discrawl", "config.toml"))
+	require.ErrorContains(t, err, "discrawl init")
+	require.ErrorContains(t, err, "--config")
+	require.ErrorContains(t, err, config.DefaultConfigEnv)
+}
+
 func TestCommandUsageErrors(t *testing.T) {
 	t.Parallel()