diff --git a/agents.md b/agents.md
index 94a5d46..ed9b933 100644
--- a/agents.md
+++ b/agents.md
@@ -1,5 +1,4 @@
 # Agents Upgrade Plan
 
-- refactor: simplify provider/session coupling so compute_web_search_settings shares normalization utilities
 - docs: clarify cloud vs local env configuration (api key precedence, insecure toggle) in configuration guide
 - ci: add targeted regression job for ollama providers covering chat, streaming, and tool execution paths
diff --git a/crates/owlen-core/src/providers/ollama.rs b/crates/owlen-core/src/providers/ollama.rs
index 71acde9..e7fdf69 100644
--- a/crates/owlen-core/src/providers/ollama.rs
+++ b/crates/owlen-core/src/providers/ollama.rs
@@ -2025,6 +2025,10 @@ fn map_reqwest_error(action: &str, err: reqwest::Error) -> Error {
     }
 }
 
+pub(crate) fn normalize_cloud_base_url(input: Option<&str>) -> std::result::Result<String, String> {
+    normalize_base_url(input, OllamaMode::Cloud)
+}
+
 fn normalize_base_url(
     input: Option<&str>,
     mode_hint: OllamaMode,
diff --git a/crates/owlen-core/src/session.rs b/crates/owlen-core/src/session.rs
index d324d69..86a0de3 100644
--- a/crates/owlen-core/src/session.rs
+++ b/crates/owlen-core/src/session.rs
@@ -19,6 +19,7 @@ use crate::mode::Mode;
 use crate::model::{DetailedModelInfo, ModelManager};
 use crate::oauth::{DeviceAuthorization, DevicePollState, OAuthClient};
 use crate::providers::OllamaProvider;
+use crate::providers::ollama::normalize_cloud_base_url;
 use crate::storage::{SessionMeta, StorageManager};
 use crate::tools::{WEB_SEARCH_TOOL_NAME, canonical_tool_name, tool_name_matches};
 use crate::types::{
@@ -187,11 +188,17 @@ fn compute_web_search_settings(
         return Ok(None);
     }
 
-    let base_url = provider_config
+    let raw_base_url = provider_config
         .base_url
         .as_deref()
-        .filter(|value| !value.trim().is_empty())
-        .unwrap_or(OLLAMA_CLOUD_BASE_URL);
+        .filter(|value| !value.trim().is_empty());
+    let normalized_base_url = normalize_cloud_base_url(raw_base_url).map_err(|err| {
+        let display_base = raw_base_url.unwrap_or(OLLAMA_CLOUD_BASE_URL);
+        Error::Config(format!(
+            "Invalid Ollama Cloud base_url '{}': {err}",
+            display_base
+        ))
+    })?;
 
     let endpoint = provider_config
         .extra
@@ -199,7 +206,7 @@ fn compute_web_search_settings(
         .and_then(|value| value.as_str())
         .unwrap_or("/api/web_search");
 
-    let endpoint_url = build_search_url(base_url, endpoint)?;
+    let endpoint_url = build_search_url(&normalized_base_url, endpoint)?;
 
     let api_key = resolve_web_search_api_key(provider_config)
         .or_else(|| env_var_non_empty(OLLAMA_API_KEY_ENV))
diff --git a/crates/owlen-core/tests/ollama_wiremock.rs b/crates/owlen-core/tests/ollama_wiremock.rs
index bdaeff6..d456385 100644
--- a/crates/owlen-core/tests/ollama_wiremock.rs
+++ b/crates/owlen-core/tests/ollama_wiremock.rs
@@ -373,7 +373,7 @@ async fn cloud_tool_call_flows_through_web_search() {
 
 #[tokio::test(flavor = "multi_thread")]
 async fn cloud_tool_call_accepts_v1_base_url() {
-    run_cloud_tool_flow("/v1", Some("/web/search"), "/v1/web/search").await;
+    run_cloud_tool_flow("/v1", Some("/web/search"), "/web/search").await;
 }
 
 #[tokio::test(flavor = "multi_thread")]