diff --git a/crates/service/src/gateway/request/official_responses_http.rs b/crates/service/src/gateway/request/official_responses_http.rs
index 5d5587743..c1c3ea2ac 100644
--- a/crates/service/src/gateway/request/official_responses_http.rs
+++ b/crates/service/src/gateway/request/official_responses_http.rs
@@ -348,6 +348,45 @@ fn ensure_tools_list(path: &str, obj: &mut Map<String, Value>) -> bool {
     }
 }
 
+// Historical hosted search calls need a matching tool declaration even when
+// Codex sends no tools during context compaction. If there were no tools,
+// preserve that intent by disabling new tool calls.
+fn ensure_historical_web_search_tool(path: &str, obj: &mut Map<String, Value>) -> bool {
+    if !is_standard_responses_path(path) {
+        return false;
+    }
+    let has_search_history = obj
+        .get("input")
+        .and_then(Value::as_array)
+        .is_some_and(|input| {
+            input
+                .iter()
+                .any(|item| item.get("type").and_then(Value::as_str) == Some("web_search_call"))
+        });
+    if !has_search_history {
+        return false;
+    }
+    let Some(tools) = obj.get_mut("tools").and_then(Value::as_array_mut) else {
+        return false;
+    };
+    if tools.iter().any(|tool| {
+        tool.get("type")
+            .and_then(Value::as_str)
+            .is_some_and(|kind| kind.starts_with("web_search"))
+    }) {
+        return false;
+    }
+    let had_no_tools = tools.is_empty();
+    tools.push(serde_json::json!({
+        "type": "web_search",
+        "external_web_access": false
+    }));
+    if had_no_tools {
+        obj.insert("tool_choice".to_string(), Value::String("none".to_string()));
+    }
+    true
+}
+
 fn ensure_parallel_tool_calls_bool(path: &str, obj: &mut Map<String, Value>) -> bool {
     if !is_responses_path(path) {
         return false;
@@ -651,6 +690,11 @@ pub(crate) fn apply_codex_http_request_rules(
             result.changed = true;
         }
     }
+    // Native Codex skips compatibility defaults, but still needs a matching
+    // hosted-tool declaration when replaying search history during compaction.
+    if ensure_historical_web_search_tool(path, obj) {
+        result.changed = true;
+    }
     if !is_compact_path(path) {
         let had_stream_passthrough = obj.contains_key("stream_passthrough");
         if use_codex_compat_rewrite {
diff --git a/crates/service/src/gateway/request/tests/request_rewrite_tests.rs b/crates/service/src/gateway/request/tests/request_rewrite_tests.rs
index b77b0fb2b..4002c86b2 100644
--- a/crates/service/src/gateway/request/tests/request_rewrite_tests.rs
+++ b/crates/service/src/gateway/request/tests/request_rewrite_tests.rs
@@ -1747,6 +1747,138 @@ fn responses_defaults_tool_choice_and_reasoning_include_for_codex_backend() {
     }));
 }
 
+#[test]
+fn responses_historical_web_search_also_repairs_native_codex_requests() {
+    let _guard = crate::test_env_guard();
+    let body = json!({
+        "model": "gpt-6.1-sol",
+        "input": [{"type": "web_search_call", "id": "ws_old", "status": "completed"}],
+        "tools": [],
+        "tool_choice": "auto",
+        "stream": false,
+        "store": true
+    });
+    let out = apply_request_overrides_with_service_tier_and_prompt_cache_key_scope(
+        "/v1/responses",
+        serde_json::to_vec(&body).expect("serialize request"),
+        None,
+        None,
+        None,
+        Some("https://chatgpt.com/backend-api/codex"),
+        None,
+        false,
+    );
+    let value: serde_json::Value = serde_json::from_slice(&out).expect("parse request");
+    assert_eq!(value["input"], body["input"]);
+    assert_eq!(
+        value["tools"],
+        json!([{"type": "web_search", "external_web_access": false}])
+    );
+    assert_eq!(value["tool_choice"], "none");
+    assert_eq!(value["stream"], false);
+    assert_eq!(value["store"], true);
+}
+
+#[test]
+fn responses_declares_historical_web_search_without_enabling_new_searches() {
+    let _guard = crate::test_env_guard();
+    let body = json!({
+        "model": "gpt-6.1-sol",
+        "input": [
+            {"type": "web_search_call", "id": "ws_old", "status": "completed"},
+            {"type": "message", "role": "assistant", "content": [{"type": "output_text", "text": "result"}]}
+        ],
+        "tools": [],
+        "tool_choice": "auto"
+    });
+    let out = apply_codex_compat_request_overrides(
+        "/v1/responses",
+        serde_json::to_vec(&body).expect("serialize request"),
+        None,
+        None,
+        Some("https://chatgpt.com/backend-api/codex"),
+    );
+    let value: serde_json::Value = serde_json::from_slice(&out).expect("parse request");
+    assert_eq!(value["input"], body["input"]);
+    assert_eq!(
+        value["tools"],
+        json!([{"type": "web_search", "external_web_access": false}])
+    );
+    assert_eq!(value["tool_choice"], "none");
+}
+
+#[test]
+fn responses_historical_web_search_preserves_other_tools_and_existing_declaration() {
+    let _guard = crate::test_env_guard();
+    let history = json!([{"type": "web_search_call", "id": "ws_old"}]);
+    let function = json!({"type": "function", "name": "ping", "parameters": {"type": "object"}});
+    for tools in [
+        json!([function]),
+        json!([{"type": "web_search", "external_web_access": true}]),
+    ] {
+        let body = json!({
+            "model": "gpt-6.1-sol",
+            "input": history,
+            "tools": tools,
+            "tool_choice": "auto"
+        });
+        let out = apply_codex_compat_request_overrides(
+            "/v1/responses",
+            serde_json::to_vec(&body).expect("serialize request"),
+            None,
+            None,
+            Some("https://chatgpt.com/backend-api/codex"),
+        );
+        let value: serde_json::Value = serde_json::from_slice(&out).expect("parse request");
+        assert_eq!(value["tool_choice"], "auto");
+        let expected_len = if tools[0]["type"] == "function" { 2 } else { 1 };
+        assert_eq!(value["tools"].as_array().unwrap().len(), expected_len);
+        assert_eq!(value["tools"][0], tools[0]);
+    }
+}
+
+#[test]
+fn responses_historical_web_search_fix_is_codex_backend_only() {
+    let _guard = crate::test_env_guard();
+    let body = json!({
+        "model": "gpt-6.1-sol",
+        "input": [{"type": "web_search_call", "id": "ws_old"}],
+        "tools": []
+    });
+    for (path, upstream) in [
+        ("/v1/responses", "https://example.org/v1"),
+        (
+            "/v1/responses/compact",
+            "https://chatgpt.com/backend-api/codex",
+        ),
+    ] {
+        let out = apply_codex_compat_request_overrides(
+            path,
+            serde_json::to_vec(&body).expect("serialize request"),
+            None,
+            None,
+            Some(upstream),
+        );
+        let value: serde_json::Value = serde_json::from_slice(&out).expect("parse request");
+        assert_eq!(value["tools"], json!([]));
+    }
+    let no_history = json!({
+        "model": "gpt-6.1-sol",
+        "input": [{"role": "user", "content": "hello"}],
+        "tools": []
+    });
+    let out = apply_codex_compat_request_overrides(
+        "/v1/responses",
+        serde_json::to_vec(&no_history).expect("serialize request"),
+        None,
+        None,
+        Some("https://chatgpt.com/backend-api/codex"),
+    );
+    let value: serde_json::Value = serde_json::from_slice(&out).expect("parse request");
+    assert_eq!(value["tools"], json!([]));
+    assert_eq!(value["tool_choice"], "auto");
+}
+
 #[test]
 fn responses_preserve_specific_function_tool_choice_object() {
     let _guard = crate::test_env_guard();