diff --git a/codex-rs/Cargo.lock b/codex-rs/Cargo.lock
index 504b37be..4961486e 100644
--- a/codex-rs/Cargo.lock
+++ b/codex-rs/Cargo.lock
@@ -992,6 +992,7 @@ dependencies = [
  "supports-color",
  "tempfile",
  "tokio",
+ "toml",
 ]
 
 [[package]]
diff --git a/codex-rs/cli/Cargo.toml b/codex-rs/cli/Cargo.toml
index b5c5b33b..041644b3 100644
--- a/codex-rs/cli/Cargo.toml
+++ b/codex-rs/cli/Cargo.toml
@@ -39,6 +39,7 @@ ctor = { workspace = true }
 owo-colors = { workspace = true }
 serde_json = { workspace = true }
 supports-color = { workspace = true }
+toml = { workspace = true }
 tokio = { workspace = true, features = [
     "io-std",
     "macros",
diff --git a/codex-rs/cli/src/main.rs b/codex-rs/cli/src/main.rs
index 9b2d106c..929fd9e7 100644
--- a/codex-rs/cli/src/main.rs
+++ b/codex-rs/cli/src/main.rs
@@ -510,15 +510,21 @@ async fn cli_main(codex_linux_sandbox_exe: Option<PathBuf>) -> anyhow::Result<()
         Some(Subcommand::Features(FeaturesCli { sub })) => match sub {
             FeaturesSubcommand::List => {
                 // Respect root-level `-c` overrides plus top-level flags like `--profile`.
-                let cli_kv_overrides = root_config_overrides
+                let mut cli_kv_overrides = root_config_overrides
                     .parse_overrides()
                     .map_err(anyhow::Error::msg)?;
 
+                // Honor `--search` via the new feature toggle.
+                if interactive.web_search {
+                    cli_kv_overrides.push((
+                        "features.web_search_request".to_string(),
+                        toml::Value::Boolean(true),
+                    ));
+                }
+
                 // Thread through relevant top-level flags (at minimum, `--profile`).
-                // Also honor `--search` since it maps to a feature toggle.
                 let overrides = ConfigOverrides {
                     config_profile: interactive.config_profile.clone(),
-                    tools_web_search_request: interactive.web_search.then_some(true),
                     ..Default::default()
                 };
 
diff --git a/codex-rs/tui/src/lib.rs b/codex-rs/tui/src/lib.rs
index 67df8562..99312ec1 100644
--- a/codex-rs/tui/src/lib.rs
+++ b/codex-rs/tui/src/lib.rs
@@ -94,7 +94,7 @@ use std::io::Write as _;
 // (tests access modules directly within the crate)
 
 pub async fn run_main(
-    cli: Cli,
+    mut cli: Cli,
     codex_linux_sandbox_exe: Option<PathBuf>,
 ) -> std::io::Result<AppExitInfo> {
     let (sandbox_mode, approval_policy) = if cli.full_auto {
@@ -114,6 +114,13 @@ pub async fn run_main(
         )
     };
 
+    // Map the legacy --search flag to the new feature toggle.
+    if cli.web_search {
+        cli.config_overrides
+            .raw_overrides
+            .push("features.web_search_request=true".to_string());
+    }
+
     // When using `--oss`, let the bootstrapper pick the model (defaulting to
     // gpt-oss:20b) and ensure it is present locally. Also, force the built‑in
     // `oss` model provider.
@@ -149,7 +156,7 @@ pub async fn run_main(
         compact_prompt: None,
         include_apply_patch_tool: None,
         show_raw_agent_reasoning: cli.oss.then_some(true),
-        tools_web_search_request: cli.web_search.then_some(true),
+        tools_web_search_request: None,
         experimental_sandbox_command_assessment: None,
         additional_writable_roots: additional_dirs,
     };