diff --git a/cli/src/main.rs b/cli/src/main.rs
index cb3e71f5ea..c6ccc7ec8c 100644
--- a/cli/src/main.rs
+++ b/cli/src/main.rs
@@ -16,7 +16,7 @@ use solana_cli_config::{Config, CONFIG_FILE};
 use solana_remote_wallet::remote_wallet::{maybe_wallet_manager, RemoteWalletManager};
 use std::{error, sync::Arc};
 
-fn parse_settings(matches: &ArgMatches<'_>) -> Result<bool, Box<dyn error::Error>> {
+fn parse_settings(matches: &ArgMatches<'_>) -> Result<Option<bool>, Box<dyn error::Error>> {
     let parse_args = match matches.subcommand() {
         ("config", Some(matches)) => match matches.subcommand() {
             ("get", Some(subcommand_matches)) => {
@@ -54,7 +54,7 @@ fn parse_settings(matches: &ArgMatches<'_>) -> Result<bool, Box<dyn error::Error
                         style("No config file found.").bold()
                     );
                 }
-                false
+                None
             }
             ("set", Some(subcommand_matches)) => {
                 if let Some(config_file) = matches.value_of("config_file") {
@@ -94,11 +94,19 @@ fn parse_settings(matches: &ArgMatches<'_>) -> Result<bool, Box<dyn error::Error
                         style("No config file found.").bold()
                     );
                 }
-                false
+                None
             }
             _ => unreachable!(),
         },
-        _ => true,
+        _ => {
+            let need_wallet_manager = if let Some(config_file) = matches.value_of("config_file") {
+                let config = Config::load(config_file).unwrap_or_default();
+                check_for_usb([config.keypair_path].iter())
+            } else {
+                false
+            };
+            Some(need_wallet_manager)
+        }
     };
     Ok(parse_args)
 }
@@ -262,8 +270,8 @@ fn do_main(
     matches: &ArgMatches<'_>,
     need_wallet_manager: bool,
 ) -> Result<(), Box<dyn error::Error>> {
-    if parse_settings(&matches)? {
-        let wallet_manager = if need_wallet_manager {
+    if let Some(config_need_wallet_manager) = parse_settings(&matches)? {
+        let wallet_manager = if need_wallet_manager || config_need_wallet_manager {
             maybe_wallet_manager()?
         } else {
             None
diff --git a/keygen/src/keygen.rs b/keygen/src/keygen.rs
index 0642fefb9b..484f0f7bd6 100644
--- a/keygen/src/keygen.rs
+++ b/keygen/src/keygen.rs
@@ -407,11 +407,12 @@ fn do_main(matches: &ArgMatches<'_>) -> Result<(), Box<dyn error::Error>> {
         Config::default()
     };
 
-    let wallet_manager = if check_for_usb(std::env::args()) {
-        maybe_wallet_manager()?
-    } else {
-        None
-    };
+    let wallet_manager =
+        if check_for_usb(std::env::args()) || check_for_usb([config.keypair_path.clone()].iter()) {
+            maybe_wallet_manager()?
+        } else {
+            None
+        };
 
     match matches.subcommand() {
         ("pubkey", Some(matches)) => {