diff --git a/src-tauri/src/commands.rs b/src-tauri/src/commands.rs
index 790d5602..e6d9980b 100644
--- a/src-tauri/src/commands.rs
+++ b/src-tauri/src/commands.rs
@@ -194,6 +194,7 @@ pub async fn expand_ssh_connection_params<R: Runtime>(
             expanded_params.ssh_password = ssh_conn.password.clone();
             expanded_params.ssh_key_file = ssh_conn.key_file.clone();
             expanded_params.ssh_key_passphrase = ssh_conn.key_passphrase.clone();
+            expanded_params.ssh_allow_passphrase_prompt = ssh_conn.allow_passphrase_prompt;
         }
     }
 
@@ -258,6 +259,7 @@ pub fn resolve_connection_params(params: &ConnectionParams) -> Result<Connection
         params.ssh_password.as_deref(),
         params.ssh_key_file.as_deref(),
         params.ssh_key_passphrase.as_deref(),
+        params.ssh_allow_passphrase_prompt.unwrap_or(false),
         remote_host,
         remote_port,
     )
@@ -972,6 +974,7 @@ async fn migrate_ssh_connections<R: Runtime>(app: &AppHandle<R>) -> Result<(), S
                             Some(key_file.clone())
                         },
                         key_passphrase: None,
+                        allow_passphrase_prompt: None,
                         save_in_keychain: conn.params.save_in_keychain,
                     };
 
@@ -1139,6 +1142,7 @@ pub async fn save_ssh_connection<R: Runtime>(
         } else {
             ssh.key_passphrase.clone()
         },
+        allow_passphrase_prompt: ssh.allow_passphrase_prompt,
         save_in_keychain: ssh.save_in_keychain,
     };
 
@@ -1206,6 +1210,7 @@ pub async fn update_ssh_connection<R: Runtime>(
         } else {
             ssh.key_passphrase.clone()
         },
+        allow_passphrase_prompt: ssh.allow_passphrase_prompt,
         save_in_keychain: ssh.save_in_keychain,
     };
 
@@ -1302,6 +1307,7 @@ pub async fn test_ssh_connection<R: Runtime>(
         resolved_password.as_deref(),
         ssh.key_file.as_deref(),
         resolved_passphrase.as_deref(),
+        ssh.allow_passphrase_prompt.unwrap_or(false),
     )
 }
 
@@ -1695,6 +1701,7 @@ mod tests {
                 password: password.map(|p| p.to_string()),
                 key_file: None,
                 key_passphrase: None,
+                allow_passphrase_prompt: None,
                 save_in_keychain: Some(save_in_keychain),
             }
         }
diff --git a/src-tauri/src/export_import_tests.rs b/src-tauri/src/export_import_tests.rs
index 13bc7621..73f26ca2 100644
--- a/src-tauri/src/export_import_tests.rs
+++ b/src-tauri/src/export_import_tests.rs
@@ -52,6 +52,7 @@ mod tests {
                 password: Some("ssh_password".to_string()),
                 key_file: None,
                 key_passphrase: None,
+                allow_passphrase_prompt: None,
                 save_in_keychain: Some(true),
             }],
         };
diff --git a/src-tauri/src/models.rs b/src-tauri/src/models.rs
index 6261201a..abfdd15d 100644
--- a/src-tauri/src/models.rs
+++ b/src-tauri/src/models.rs
@@ -80,6 +80,8 @@ pub struct SshConnection {
     pub key_file: Option<String>,
     #[serde(skip_serializing_if = "Option::is_none")]
     pub key_passphrase: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub allow_passphrase_prompt: Option<bool>,
     pub save_in_keychain: Option<bool>,
 }
 
@@ -95,6 +97,8 @@ pub struct SshConnectionInput {
     pub key_file: Option<String>,
     #[serde(skip_serializing_if = "Option::is_none")]
     pub key_passphrase: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub allow_passphrase_prompt: Option<bool>,
     pub save_in_keychain: Option<bool>,
 }
 
@@ -110,6 +114,8 @@ pub struct SshTestParams {
     #[serde(skip_serializing_if = "Option::is_none")]
     pub key_passphrase: Option<String>,
     #[serde(skip_serializing_if = "Option::is_none")]
+    pub allow_passphrase_prompt: Option<bool>,
+    #[serde(skip_serializing_if = "Option::is_none")]
     pub connection_id: Option<String>,
 }
 
@@ -141,6 +147,8 @@ pub struct ConnectionParams {
     pub ssh_key_file: Option<String>,
     #[serde(skip_serializing_if = "Option::is_none")]
     pub ssh_key_passphrase: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub ssh_allow_passphrase_prompt: Option<bool>,
     pub save_in_keychain: Option<bool>,
     // Connection ID for stable pooling (not persisted, set at runtime)
     #[serde(skip_serializing_if = "Option::is_none")]
diff --git a/src-tauri/src/ssh_tunnel.rs b/src-tauri/src/ssh_tunnel.rs
index d9f9492a..af7c938e 100644
--- a/src-tauri/src/ssh_tunnel.rs
+++ b/src-tauri/src/ssh_tunnel.rs
@@ -95,13 +95,14 @@ impl SshTunnel {
         ssh_password: Option<&str>,
         ssh_key_file: Option<&str>,
         ssh_key_passphrase: Option<&str>,
+        ssh_allow_passphrase_prompt: bool,
         remote_host: &str,
         remote_port: u16,
     ) -> Result<Self, String> {
         let use_system_ssh = should_use_system_ssh(ssh_password);
         println!(
-            "[SSH Tunnel] New Request: Host={}, Port={}, User={}, UseSystemSSH={}",
-            ssh_host, ssh_port, ssh_user, use_system_ssh
+            "[SSH Tunnel] New Request: Host={}, Port={}, User={}, UseSystemSSH={}, AllowPrompt={}",
+            ssh_host, ssh_port, ssh_user, use_system_ssh, ssh_allow_passphrase_prompt
         );
 
         let local_port = {
@@ -120,6 +121,7 @@ impl SshTunnel {
                 ssh_port,
                 ssh_user,
                 ssh_key_file,
+                ssh_allow_passphrase_prompt,
                 remote_host,
                 remote_port,
                 local_port,
@@ -152,6 +154,7 @@ impl SshTunnel {
         ssh_port: u16,
         ssh_user: &str,
         ssh_key_file: Option<&str>,
+        ssh_allow_passphrase_prompt: bool,
         remote_host: &str,
         remote_port: u16,
         local_port: u16,
@@ -188,18 +191,27 @@ impl SshTunnel {
         args.push("-o".to_string());
         args.push("StrictHostKeyChecking=accept-new".to_string());
         args.push("-o".to_string());
-        args.push("BatchMode=yes".to_string());
+        if ssh_allow_passphrase_prompt {
+            args.push("BatchMode=no".to_string());
+        } else {
+            args.push("BatchMode=yes".to_string());
+        }
 
         args.push(destination);
 
         println!("[SSH Tunnel] Executing: ssh {:?}", args);
 
-        let mut child = Command::new("ssh")
+        let mut command = Command::new("ssh");
+        command
             .args(&args)
             .stdout(Stdio::piped())
-            .stderr(Stdio::piped())
-            .spawn()
-            .map_err(|e| {
+            .stderr(Stdio::piped());
+
+        if ssh_allow_passphrase_prompt {
+            command.env("SSH_ASKPASS_REQUIRE", "force");
+        }
+
+        let mut child = command.spawn().map_err(|e| {
                 let err = format!(
                     "Failed to launch system ssh: {}. Ensure 'ssh' is in PATH.",
                     e
@@ -526,15 +538,22 @@ pub fn test_ssh_connection(
     ssh_password: Option<&str>,
     ssh_key_file: Option<&str>,
     ssh_key_passphrase: Option<&str>,
+    ssh_allow_passphrase_prompt: bool,
 ) -> Result<String, String> {
     let use_system_ssh = should_use_system_ssh(ssh_password);
     println!(
-        "[SSH Test] Testing connection to {}:{} as {} (UseSystemSSH={})",
-        ssh_host, ssh_port, ssh_user, use_system_ssh
+        "[SSH Test] Testing connection to {}:{} as {} (UseSystemSSH={}, AllowPrompt={})",
+        ssh_host, ssh_port, ssh_user, use_system_ssh, ssh_allow_passphrase_prompt
     );
 
     if use_system_ssh {
-        test_ssh_connection_system(ssh_host, ssh_port, ssh_user, ssh_key_file)
+        test_ssh_connection_system(
+            ssh_host,
+            ssh_port,
+            ssh_user,
+            ssh_key_file,
+            ssh_allow_passphrase_prompt,
+        )
     } else {
         test_ssh_connection_russh(
             ssh_host,
@@ -553,6 +572,7 @@ fn test_ssh_connection_system(
     ssh_port: u16,
     ssh_user: &str,
     ssh_key_file: Option<&str>,
+    ssh_allow_passphrase_prompt: bool,
 ) -> Result<String, String> {
     println!("[SSH Test] Using system SSH (supports ~/.ssh/config)");
 
@@ -563,7 +583,11 @@ fn test_ssh_connection_system(
     let mut args = Vec::with_capacity(12);
     args.extend([
         "-o",
-        "BatchMode=yes",
+        if ssh_allow_passphrase_prompt {
+            "BatchMode=no"
+        } else {
+            "BatchMode=yes"
+        },
         "-o",
         "ConnectTimeout=10",
         "-o",
@@ -585,7 +609,14 @@ fn test_ssh_connection_system(
 
     println!("[SSH Test] Executing: ssh {:?}", args);
 
-    let output = Command::new("ssh").args(&args).output().map_err(|e| {
+    let mut command = Command::new("ssh");
+    command.args(&args);
+
+    if ssh_allow_passphrase_prompt {
+        command.env("SSH_ASKPASS_REQUIRE", "force");
+    }
+
+    let output = command.output().map_err(|e| {
         format!(
             "Failed to execute ssh command: {}. Ensure 'ssh' is in PATH.",
             e
diff --git a/src/components/modals/NewConnectionModal.tsx b/src/components/modals/NewConnectionModal.tsx
index 4790d098..d1de710a 100644
--- a/src/components/modals/NewConnectionModal.tsx
+++ b/src/components/modals/NewConnectionModal.tsx
@@ -59,6 +59,7 @@ interface ConnectionParams {
   ssh_password?: string;
   ssh_key_file?: string;
   ssh_key_passphrase?: string;
+  ssh_allow_passphrase_prompt?: boolean;
   save_in_keychain?: boolean;
 }
 
@@ -1432,6 +1433,23 @@ export const NewConnectionModal = ({
                 type="password"
                 placeholder={t("newConnection.sshKeyPassphrasePlaceholder")}
               />
+              <div className="flex items-center gap-2 mt-1">
+                <input
+                  type="checkbox"
+                  id="ssh-prompt-toggle"
+                  checked={!!formData.ssh_allow_passphrase_prompt}
+                  onChange={(e) =>
+                    updateField("ssh_allow_passphrase_prompt", e.target.checked)
+                  }
+                  className="accent-blue-500 w-3.5 h-3.5 rounded cursor-pointer"
+                />
+                <label
+                  htmlFor="ssh-prompt-toggle"
+                  className="text-xs font-medium text-secondary cursor-pointer select-none"
+                >
+                  {t("newConnection.allowSshPrompt")}
+                </label>
+              </div>
             </div>
           )}
         </div>
diff --git a/src/components/modals/SshConnectionsModal.tsx b/src/components/modals/SshConnectionsModal.tsx
index 3baabaf2..a6420812 100644
--- a/src/components/modals/SshConnectionsModal.tsx
+++ b/src/components/modals/SshConnectionsModal.tsx
@@ -217,6 +217,7 @@ export function SshConnectionsModal({
         password: formData.password,
         key_file: formData.key_file,
         key_passphrase: formData.key_passphrase,
+        allow_passphrase_prompt: formData.allow_passphrase_prompt,
         save_in_keychain: formData.save_in_keychain,
       };
 
@@ -559,6 +560,24 @@ export function SshConnectionsModal({
                 </label>
               </div>
 
+              <div className="flex items-center gap-2">
+                <input
+                  type="checkbox"
+                  id="ssh-prompt-toggle"
+                  checked={!!formData.allow_passphrase_prompt}
+                  onChange={(e) => {
+                    updateField("allow_passphrase_prompt", e.target.checked);
+                  }}
+                  className="accent-blue-500 w-4 h-4 rounded cursor-pointer"
+                />
+                <label
+                  htmlFor="ssh-prompt-toggle"
+                  className="text-sm font-medium text-secondary cursor-pointer select-none"
+                >
+                  {t("newConnection.allowSshPrompt")}
+                </label>
+              </div>
+
               {/* Test Button and Status */}
               <div className="pt-4 border-t border-strong">
                 <button
diff --git a/src/i18n/locales/de.json b/src/i18n/locales/de.json
index a06f07f1..5e633cdd 100644
--- a/src/i18n/locales/de.json
+++ b/src/i18n/locales/de.json
@@ -639,6 +639,7 @@
     "sshKeyFilePlaceholder": "/pfad/zu/id_rsa",
     "sshKeyPassphrase": "Passphrase für SSH-Schlüssel (optional)",
     "sshKeyPassphrasePlaceholder": "Passphrase eingeben, falls der Schlüssel verschlüsselt ist",
+    "allowSshPrompt": "SSH-Passwort/PIN-Eingabeaufforderung erlauben",
     "saveKeychain": "Passwörter im Keychain speichern",
     "testConnection": "Verbindung testen",
     "save": "Speichern",
diff --git a/src/i18n/locales/en.json b/src/i18n/locales/en.json
index 02a32a55..1bbffa44 100644
--- a/src/i18n/locales/en.json
+++ b/src/i18n/locales/en.json
@@ -660,6 +660,7 @@
     "sshKeyFilePlaceholder": "/path/to/id_rsa",
     "sshKeyPassphrase": "SSH Key Passphrase (Optional)",
     "sshKeyPassphrasePlaceholder": "Enter key passphrase if encrypted",
+    "allowSshPrompt": "Allow SSH password/PIN prompt",
     "saveKeychain": "Save passwords in Keychain",
     "testConnection": "Test Connection",
     "save": "Save",
diff --git a/src/i18n/locales/es.json b/src/i18n/locales/es.json
index 6b54ee1e..e4585c39 100644
--- a/src/i18n/locales/es.json
+++ b/src/i18n/locales/es.json
@@ -644,6 +644,7 @@
     "sshKeyFilePlaceholder": "/ruta/a/id_rsa",
     "sshKeyPassphrase": "Frase de Paso de Clave SSH (Opcional)",
     "sshKeyPassphrasePlaceholder": "Ingresa la frase de paso si la clave está cifrada",
+    "allowSshPrompt": "Permitir solicitud de contraseña/PIN de SSH",
     "saveKeychain": "Guardar contraseñas en el Llavero",
     "testConnection": "Probar Conexión",
     "save": "Guardar",
diff --git a/src/i18n/locales/fr.json b/src/i18n/locales/fr.json
index 35f25680..b9a9832d 100644
--- a/src/i18n/locales/fr.json
+++ b/src/i18n/locales/fr.json
@@ -639,6 +639,7 @@
     "sshKeyFilePlaceholder": "/chemin/vers/id_rsa",
     "sshKeyPassphrase": "Phrase secrète de clé SSH (optionnel)",
     "sshKeyPassphrasePlaceholder": "Saisissez la phrase secrète si la clé est chiffrée",
+    "allowSshPrompt": "Autoriser l'invite de mot de passe/PIN SSH",
     "saveKeychain": "Enregistrer les mots de passe dans le trousseau",
     "testConnection": "Tester la connexion",
     "save": "Enregistrer",
diff --git a/src/i18n/locales/it.json b/src/i18n/locales/it.json
index e4be8630..271ac4fc 100644
--- a/src/i18n/locales/it.json
+++ b/src/i18n/locales/it.json
@@ -644,6 +644,7 @@
     "sshKeyFilePlaceholder": "/percorso/id_rsa",
     "sshKeyPassphrase": "Passphrase Chiave SSH (Opzionale)",
     "sshKeyPassphrasePlaceholder": "Inserisci passphrase se la chiave è cifrata",
+    "allowSshPrompt": "Consenti prompt password/PIN SSH",
     "saveKeychain": "Salva password nel Portachiavi",
     "testConnection": "Testa Connessione",
     "save": "Salva",
diff --git a/src/i18n/locales/ja.json b/src/i18n/locales/ja.json
index 06d38178..8f4fbaa5 100644
--- a/src/i18n/locales/ja.json
+++ b/src/i18n/locales/ja.json
@@ -653,6 +653,7 @@
     "sshKeyFilePlaceholder": "/path/to/id_rsa",
     "sshKeyPassphrase": "SSH 鍵のパスフレーズ (任意)",
     "sshKeyPassphrasePlaceholder": "鍵が暗号化されている場合はパスフレーズを入力",
+    "allowSshPrompt": "SSHパスワード/PINプロンプトを許可する",
     "saveKeychain": "パスワードをキーチェーンに保存",
     "testConnection": "接続テスト",
     "save": "保存",
diff --git a/src/i18n/locales/ru.json b/src/i18n/locales/ru.json
index 724cd97f..f83cad04 100644
--- a/src/i18n/locales/ru.json
+++ b/src/i18n/locales/ru.json
@@ -633,6 +633,7 @@
     "sshKeyFilePlaceholder": "/path/to/id_rsa",
     "sshKeyPassphrase": "Пароль SSH-ключа (необязательно)",
     "sshKeyPassphrasePlaceholder": "Введите пароль, если ключ зашифрован",
+    "allowSshPrompt": "Разрешить запрос пароля/PIN-кода SSH",
     "saveKeychain": "Сохранять пароли в Keychain",
     "testConnection": "Проверить подключение",
     "save": "Сохранить",
diff --git a/src/i18n/locales/zh.json b/src/i18n/locales/zh.json
index 7aaf5248..db5d4412 100644
--- a/src/i18n/locales/zh.json
+++ b/src/i18n/locales/zh.json
@@ -607,6 +607,7 @@
     "sshKeyFilePlaceholder": "/path/to/id_rsa",
     "sshKeyPassphrase": "SSH 密钥密码（可选）",
     "sshKeyPassphrasePlaceholder": "如果加密请输入密钥密码",
+    "allowSshPrompt": "允许 SSH 密码/PIN 提示",
     "saveKeychain": "在密钥链中保存密码",
     "testConnection": "测试连接",
     "save": "保存",
diff --git a/src/utils/connections.ts b/src/utils/connections.ts
index ece0aca2..39129b77 100644
--- a/src/utils/connections.ts
+++ b/src/utils/connections.ts
@@ -28,6 +28,7 @@ export interface ConnectionParams {
   ssh_password?: string;
   ssh_key_file?: string;
   ssh_key_passphrase?: string;
+  ssh_allow_passphrase_prompt?: boolean;
 }
 
 /**
diff --git a/src/utils/credentials.ts b/src/utils/credentials.ts
index 96359984..41f057c2 100644
--- a/src/utils/credentials.ts
+++ b/src/utils/credentials.ts
@@ -16,6 +16,7 @@ interface ConnectionParams {
   ssh_password?: string;
   ssh_key_file?: string;
   ssh_key_passphrase?: string;
+  ssh_allow_passphrase_prompt?: boolean;
   save_in_keychain?: boolean;
 }
 
diff --git a/src/utils/ssh.ts b/src/utils/ssh.ts
index 6b144ae1..7aace7bf 100644
--- a/src/utils/ssh.ts
+++ b/src/utils/ssh.ts
@@ -15,6 +15,7 @@ export interface SshConnection {
   password?: string;
   key_file?: string;
   key_passphrase?: string;
+  allow_passphrase_prompt?: boolean;
   save_in_keychain?: boolean;
 }