diff --git a/crates/goose-cli/src/scenario_tests/scenario_runner.rs b/crates/goose-cli/src/scenario_tests/scenario_runner.rs
index 085d28720a95..00a90778d3ae 100644
--- a/crates/goose-cli/src/scenario_tests/scenario_runner.rs
+++ b/crates/goose-cli/src/scenario_tests/scenario_runner.rs
@@ -218,7 +218,7 @@ where
         .update_provider(provider_arc as Arc<dyn goose::providers::base::Provider>)
         .await?;
 
-    let mut session = CliSession::new(agent, None, false, None, None, None, None);
+    let mut session = CliSession::new(agent, None, false, None, None, None, None).await;
 
     let mut error = None;
     for message in &messages {
diff --git a/crates/goose-cli/src/session/builder.rs b/crates/goose-cli/src/session/builder.rs
index 0c84f41bb983..ace3c24df65c 100644
--- a/crates/goose-cli/src/session/builder.rs
+++ b/crates/goose-cli/src/session/builder.rs
@@ -133,7 +133,7 @@ async fn offer_extension_debugging_help(
     }
 
     // Create the debugging session
-    let mut debug_session = CliSession::new(debug_agent, None, false, None, None, None, None);
+    let mut debug_session = CliSession::new(debug_agent, None, false, None, None, None, None).await;
 
     // Process the debugging request
     println!("{}", style("Analyzing the extension failure...").yellow());
@@ -465,7 +465,8 @@ pub async fn build_session(session_config: SessionBuilderConfig) -> CliSession {
         session_config.max_turns,
         edit_mode,
         session_config.retry_config.clone(),
-    );
+    )
+    .await;
 
     // Add stdio extensions if provided
     for extension_str in session_config.extensions {
diff --git a/crates/goose-cli/src/session/mod.rs b/crates/goose-cli/src/session/mod.rs
index 2bb7b035df72..ea32ef089c53 100644
--- a/crates/goose-cli/src/session/mod.rs
+++ b/crates/goose-cli/src/session/mod.rs
@@ -119,7 +119,7 @@ pub async fn classify_planner_response(
 }
 
 impl CliSession {
-    pub fn new(
+    pub async fn new(
         agent: Agent,
         session_id: Option<String>,
         debug: bool,
@@ -129,14 +129,10 @@ impl CliSession {
         retry_config: Option<RetryConfig>,
     ) -> Self {
         let messages = if let Some(session_id) = &session_id {
-            tokio::task::block_in_place(|| {
-                tokio::runtime::Handle::current().block_on(async {
-                    SessionManager::get_session(session_id, true)
-                        .await
-                        .map(|session| session.conversation.unwrap_or_default())
-                        .unwrap()
-                })
-            })
+            SessionManager::get_session(session_id, true)
+                .await
+                .map(|session| session.conversation.unwrap_or_default())
+                .unwrap()
         } else {
             Conversation::new_unvalidated(Vec::new())
         };
diff --git a/crates/goose/src/session/session_manager.rs b/crates/goose/src/session/session_manager.rs
index ddd4d3f513db..0002d4199a1c 100644
--- a/crates/goose/src/session/session_manager.rs
+++ b/crates/goose/src/session/session_manager.rs
@@ -630,7 +630,7 @@ impl SessionStorage {
 
     async fn create_session(&self, working_dir: PathBuf, description: String) -> Result<Session> {
         let today = chrono::Utc::now().format("%Y%m%d").to_string();
-        Ok(sqlx::query_as(
+        let session_id = sqlx::query_as(
             r#"
                 INSERT INTO sessions (id, description, working_dir, extension_data)
                 VALUES (
@@ -651,7 +651,13 @@ impl SessionStorage {
         .bind(&description)
         .bind(working_dir.to_string_lossy().as_ref())
         .fetch_one(&self.pool)
-        .await?)
+        .await?;
+
+        sqlx::query("PRAGMA wal_checkpoint")
+            .execute(&self.pool)
+            .await?;
+
+        Ok(session_id)
     }
 
     async fn get_session(&self, id: &str, include_messages: bool) -> Result<Session> {