diff --git a/codex-rs/core/src/tools/spec.rs b/codex-rs/core/src/tools/spec.rs
index 4d7011d193..15b53a3a0b 100644
--- a/codex-rs/core/src/tools/spec.rs
+++ b/codex-rs/core/src/tools/spec.rs
@@ -508,6 +508,14 @@ impl ToolsConfig {
     }
 
     fn is_tool_capability_enabled(&self, capability: ToolCapabilityKey) -> bool {
+        if matches!(capability, ToolCapabilityKey::WebSearch) {
+            // The resolved web_search_mode already reflects config, feature defaults,
+            // and any requirement-driven overrides.
+            return self
+                .web_search_mode
+                .is_some_and(|mode| mode != WebSearchMode::Disabled);
+        }
+
         if let Some(enabled_tool_capabilities) = self.enabled_tool_capabilities.as_ref() {
             return enabled_tool_capabilities.contains(capability.capability_name());
         }
@@ -524,9 +532,6 @@ impl ToolsConfig {
             ToolCapabilityKey::ApplyPatch => self.apply_patch_tool_type.is_some(),
             ToolCapabilityKey::UpdatePlan => true,
             ToolCapabilityKey::RequestUserInput => self.request_user_input,
-            ToolCapabilityKey::WebSearch => self
-                .web_search_mode
-                .is_some_and(|mode| mode != WebSearchMode::Disabled),
             ToolCapabilityKey::ImageGeneration => self.image_gen_tool,
             ToolCapabilityKey::ViewImage => self.legacy_view_image_override.unwrap_or(true),
             ToolCapabilityKey::Artifacts => self.artifact_tools,
diff --git a/codex-rs/core/src/tools/spec_tests.rs b/codex-rs/core/src/tools/spec_tests.rs
index 49265d2807..7b74a537f7 100644
--- a/codex-rs/core/src/tools/spec_tests.rs
+++ b/codex-rs/core/src/tools/spec_tests.rs
@@ -1174,6 +1174,36 @@ fn web_search_mode_live_sets_external_web_access_true() {
     );
 }
 
+#[test]
+fn web_search_mode_overrides_enabled_tool_capabilities() {
+    let features = Features::with_defaults();
+    let available_models = Vec::new();
+    let tools_config = ToolsConfig::new(&ToolsConfigParams {
+        model_info: &search_capable_model_info(),
+        available_models: &available_models,
+        features: &features,
+        web_search_mode: Some(WebSearchMode::Live),
+        session_source: SessionSource::Cli,
+        sandbox_policy: &SandboxPolicy::DangerFullAccess,
+        windows_sandbox_level: WindowsSandboxLevel::Disabled,
+    })
+    .with_enabled_tool_capabilities(Some(BTreeSet::from(["shell".to_string()])));
+
+    let (tools, _) = build_specs(&tools_config, None, None, &[]).build();
+
+    let tool = find_tool(&tools, "web_search");
+    assert_eq!(
+        tool.spec,
+        ToolSpec::WebSearch {
+            external_web_access: Some(true),
+            filters: None,
+            user_location: None,
+            search_context_size: None,
+            search_content_types: None,
+        }
+    );
+}
+
 #[test]
 fn web_search_config_is_forwarded_to_tool_spec() {
     let config = test_config();