diff --git a/cmd/doctor.go b/cmd/doctor.go
index f14373b..cb1f2f9 100644
--- a/cmd/doctor.go
+++ b/cmd/doctor.go
@@ -38,18 +38,27 @@ func runDoctor(w io.Writer) bool {
 	}
 	hasError := false
 
+	lastFail := false
+
 	emit := func(level, msg string) {
 		var code string
 		switch level {
 		case "ok":
 			code = "32"
+			lastFail = false
 		case "WARN":
 			code = "33"
+			lastFail = false
 		case "FAIL":
 			code = "31"
 			hasError = true
+			lastFail = true
+		}
+		if lastFail && tty {
+			fmt.Fprintf(w, "%s \033[1m%s\033[0m\n", keyword(code, level, tty), msg)
+		} else {
+			fmt.Fprintf(w, "%s %s\n", keyword(code, level, tty), msg)
 		}
-		fmt.Fprintf(w, "%s %s\n", keyword(code, level, tty), msg)
 	}
 
 	tree := func(items []string) {
@@ -58,7 +67,11 @@ func runDoctor(w io.Writer) bool {
 			if i == len(items)-1 {
 				connector = "└── "
 			}
-			fmt.Fprintf(w, "      %s%s\n", connector, item)
+			if lastFail && tty {
+				fmt.Fprintf(w, "\033[1m      %s%s\033[0m\n", connector, item)
+			} else {
+				fmt.Fprintf(w, "      %s%s\n", connector, item)
+			}
 		}
 	}
 
@@ -117,6 +130,7 @@ func runDoctor(w io.Writer) bool {
 		}
 		if configErr != nil {
 			issues = append(issues, fmt.Sprintf("Parse error: %v", configErr))
+			issues = append(issues, "While broken, ONLY 'doctor', 'config edit', and 'config init' will function")
 			issues = append(issues, "Fix with 'pda config edit' or 'pda config init --new'")
 		}
 		if unexpectedFiles(cfgDir, map[string]bool{
diff --git a/cmd/doctor_test.go b/cmd/doctor_test.go
index 22780d9..4516bc7 100644
--- a/cmd/doctor_test.go
+++ b/cmd/doctor_test.go
@@ -14,6 +14,9 @@ func TestDoctorCleanEnv(t *testing.T) {
 	configDir := t.TempDir()
 	t.Setenv("PDA_DATA", dataDir)
 	t.Setenv("PDA_CONFIG", configDir)
+	saved := configErr
+	configErr = nil
+	t.Cleanup(func() { configErr = saved })
 
 	var buf bytes.Buffer
 	hasError := runDoctor(&buf)
@@ -40,6 +43,9 @@ func TestDoctorWithStores(t *testing.T) {
 	configDir := t.TempDir()
 	t.Setenv("PDA_DATA", dataDir)
 	t.Setenv("PDA_CONFIG", configDir)
+	saved := configErr
+	configErr = nil
+	t.Cleanup(func() { configErr = saved })
 
 	content := "{\"key\":\"foo\",\"value\":\"bar\",\"encoding\":\"text\"}\n" +
 		"{\"key\":\"baz\",\"value\":\"qux\",\"encoding\":\"text\"}\n"
diff --git a/cmd/msg.go b/cmd/msg.go
index ea1d7d6..20dff20 100644
--- a/cmd/msg.go
+++ b/cmd/msg.go
@@ -31,24 +31,33 @@ func stdoutIsTerminal() bool {
 }
 
 // keyword returns a right-aligned, colored keyword (color only on TTY).
+// All keywords are bold except dim (code "2").
 //
-//	FAIL  red         (stderr)
+//	FAIL  bold red    (stderr)
 //	hint  dim         (stderr)
-//	WARN  yellow      (stderr)
-//	info  blue        (stderr)
-//	  ok  green       (stderr)
-//	   ?  cyan        (stdout)
+//	WARN  bold yellow (stderr)
+//	info  bold blue   (stderr)
+//	  ok  bold green  (stderr)
+//	   ?  bold cyan   (stdout)
 //	   >  dim         (stdout)
 func keyword(code, word string, tty bool) string {
 	padded := fmt.Sprintf("%4s", word)
 	if tty {
+		if code != "2" {
+			code = "1;" + code
+		}
 		return fmt.Sprintf("\033[%sm%s\033[0m", code, padded)
 	}
 	return padded
 }
 
 func printError(err error) {
-	fmt.Fprintf(os.Stderr, "%s %s\n", keyword("31", "FAIL", stderrIsTerminal()), err)
+	tty := stderrIsTerminal()
+	if tty {
+		fmt.Fprintf(os.Stderr, "%s \033[1m%s\033[0m\n", keyword("31", "FAIL", true), err)
+	} else {
+		fmt.Fprintf(os.Stderr, "%s %s\n", keyword("31", "FAIL", false), err)
+	}
 }
 
 func printHint(format string, args ...any) {
diff --git a/cmd/root.go b/cmd/root.go
index e718397..5c01bf8 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -23,6 +23,7 @@ THE SOFTWARE.
 package cmd
 
 import (
+	"fmt"
 	"os"
 
 	"github.com/spf13/cobra"
@@ -40,7 +41,7 @@ func Execute() {
 	if configErr != nil {
 		cmd, _, _ := rootCmd.Find(os.Args[1:])
 		if !configSafeCmd(cmd) {
-			infof("Running pda! doctor")
+			printError(fmt.Errorf("fatal problem: running pda! doctor automatically"))
 			runDoctor(os.Stderr)
 			os.Exit(1)
 		}