diff --git a/codex-rs/cli/src/login.rs b/codex-rs/cli/src/login.rs
index 2b497c06..cd20e2ba 100644
--- a/codex-rs/cli/src/login.rs
+++ b/codex-rs/cli/src/login.rs
@@ -9,6 +9,8 @@ use codex_core::config::ConfigOverrides;
 use codex_login::ServerOptions;
 use codex_login::run_device_code_login;
 use codex_login::run_login_server;
+use std::io::IsTerminal;
+use std::io::Read;
 use std::path::PathBuf;
 
 pub async fn login_with_chatgpt(codex_home: PathBuf) -> std::io::Result<()> {
@@ -56,6 +58,33 @@ pub async fn run_login_with_api_key(
     }
 }
 
+pub fn read_api_key_from_stdin() -> String {
+    let mut stdin = std::io::stdin();
+
+    if stdin.is_terminal() {
+        eprintln!(
+            "--with-api-key expects the API key on stdin. Try piping it, e.g. `printenv OPENAI_API_KEY | codex login --with-api-key`."
+        );
+        std::process::exit(1);
+    }
+
+    eprintln!("Reading API key from stdin...");
+
+    let mut buffer = String::new();
+    if let Err(err) = stdin.read_to_string(&mut buffer) {
+        eprintln!("Failed to read API key from stdin: {err}");
+        std::process::exit(1);
+    }
+
+    let api_key = buffer.trim().to_string();
+    if api_key.is_empty() {
+        eprintln!("No API key provided via stdin.");
+        std::process::exit(1);
+    }
+
+    api_key
+}
+
 /// Login using the OAuth device code flow.
 pub async fn run_login_with_device_code(
     cli_config_overrides: CliConfigOverrides,
diff --git a/codex-rs/cli/src/main.rs b/codex-rs/cli/src/main.rs
index 10e26215..51c13742 100644
--- a/codex-rs/cli/src/main.rs
+++ b/codex-rs/cli/src/main.rs
@@ -7,6 +7,7 @@ use codex_chatgpt::apply_command::ApplyCommand;
 use codex_chatgpt::apply_command::run_apply_command;
 use codex_cli::LandlockCommand;
 use codex_cli::SeatbeltCommand;
+use codex_cli::login::read_api_key_from_stdin;
 use codex_cli::login::run_login_status;
 use codex_cli::login::run_login_with_api_key;
 use codex_cli::login::run_login_with_chatgpt;
@@ -139,7 +140,18 @@ struct LoginCommand {
     #[clap(skip)]
     config_overrides: CliConfigOverrides,
 
-    #[arg(long = "api-key", value_name = "API_KEY")]
+    #[arg(
+        long = "with-api-key",
+        help = "Read the API key from stdin (e.g. `printenv OPENAI_API_KEY | codex login --with-api-key`)"
+    )]
+    with_api_key: bool,
+
+    #[arg(
+        long = "api-key",
+        value_name = "API_KEY",
+        help = "(deprecated) Previously accepted the API key directly; now exits with guidance to use --with-api-key",
+        hide = true
+    )]
     api_key: Option<String>,
 
     /// EXPERIMENTAL: Use device code flow (not yet supported)
@@ -298,7 +310,13 @@ async fn cli_main(codex_linux_sandbox_exe: Option<PathBuf>) -> anyhow::Result<()
                             login_cli.client_id,
                         )
                         .await;
-                    } else if let Some(api_key) = login_cli.api_key {
+                    } else if login_cli.api_key.is_some() {
+                        eprintln!(
+                            "The --api-key flag is no longer supported. Pipe the key instead, e.g. `printenv OPENAI_API_KEY | codex login --with-api-key`."
+                        );
+                        std::process::exit(1);
+                    } else if login_cli.with_api_key {
+                        let api_key = read_api_key_from_stdin();
                         run_login_with_api_key(login_cli.config_overrides, api_key).await;
                     } else {
                         run_login_with_chatgpt(login_cli.config_overrides).await;
diff --git a/docs/authentication.md b/docs/authentication.md
index 0db35489..d2d129f8 100644
--- a/docs/authentication.md
+++ b/docs/authentication.md
@@ -5,9 +5,17 @@
 If you prefer to pay-as-you-go, you can still authenticate with your OpenAI API key:
 
 ```shell
-codex login --api-key "your-api-key-here"
+printenv OPENAI_API_KEY | codex login --with-api-key
 ```
 
+Alternatively, read from a file:
+
+```shell
+codex login --with-api-key < my_key.txt
+```
+
+The legacy `--api-key` flag now exits with an error instructing you to use `--with-api-key` so that the key never appears in shell history or process listings.
+
 This key must, at minimum, have write access to the Responses API.
 
 ## Migrating to ChatGPT login from API key