diff --git a/internal/iostreams/prompts.go b/internal/iostreams/prompts.go
index 31922327..bfa93068 100644
--- a/internal/iostreams/prompts.go
+++ b/internal/iostreams/prompts.go
@@ -271,6 +271,8 @@ func errInteractivityFlags(cfg PromptConfig, message string, options []string) e
 			}
 		}
 		remediation = fmt.Sprintf("Re-run with one of the `--%s` values shown above", flagName)
+	case len(flags) == 1 && isPasswordPrompt(cfg):
+		remediation = fmt.Sprintf("Run this command in an interactive terminal to enter the value with hidden input\nThe `--%s` flag also works, but can leave the value in shell history", flags[0].Name)
 	case len(flags) == 1:
 		remediation = fmt.Sprintf("Try running the command with the `--%s` flag included\nLearn more about this flag with `--help`", flags[0].Name)
 	case len(flags) > 1:
@@ -290,6 +292,13 @@ func errInteractivityFlags(cfg PromptConfig, message string, options []string) e
 		WithRemediation("%s", remediation)
 }
 
+// isPasswordPrompt reports whether the prompt collects a secret, such as a
+// token or a password, that is safer typed than passed as a flag.
+func isPasswordPrompt(cfg PromptConfig) bool {
+	_, ok := cfg.(PasswordPromptConfig)
+	return ok
+}
+
 // ConfirmPrompt prompts the user for a "yes" or "no" (true or false) value for
 // the message
 func (io *IOStreams) ConfirmPrompt(ctx context.Context, message string, cfg ConfirmPromptConfig) (bool, error) {
diff --git a/internal/iostreams/prompts_test.go b/internal/iostreams/prompts_test.go
index b7d1e282..07472933 100644
--- a/internal/iostreams/prompts_test.go
+++ b/internal/iostreams/prompts_test.go
@@ -194,10 +194,20 @@ func TestErrInteractivityFlags(t *testing.T) {
 			contains: []string{"not a TTY"},
 		},
 		"one flag suggests the flag name": {
+			cfg: SelectPromptConfig{
+				Flag: &pflag.Flag{Name: "team"},
+			},
+			contains: []string{"Try running the command with the `--team` flag included"},
+		},
+		"password flag suggests an interactive terminal first": {
 			cfg: PasswordPromptConfig{
 				Flag: &pflag.Flag{Name: "token"},
 			},
-			contains: []string{"--token"},
+			contains: []string{
+				"Run this command in an interactive terminal to enter the value with hidden input",
+				"The `--token` flag also works, but can leave the value in shell history",
+			},
+			excludes: []string{"Try running the command with"},
 		},
 		"multiple flags lists all flag names": {
 			cfg: SelectPromptConfig{Flags: []*pflag.Flag{