diff --git a/crates/terraphim_sessions/src/connector/mod.rs b/crates/terraphim_sessions/src/connector/mod.rs
index 8b2bc6c43..91288df53 100644
--- a/crates/terraphim_sessions/src/connector/mod.rs
+++ b/crates/terraphim_sessions/src/connector/mod.rs
@@ -153,12 +153,27 @@ impl ConnectorRegistry {
 
     /// Import sessions from all available connectors
     pub async fn import_all(&self, options: &ImportOptions) -> Result<Vec<Session>> {
+        let connectors = self.available();
+        let total_connectors = connectors.len();
         let mut all_sessions = Vec::new();
 
-        for connector in self.available() {
+        for (idx, connector) in connectors.iter().enumerate() {
+            tracing::info!(
+                "Importing from {}/{}: {}",
+                idx + 1,
+                total_connectors,
+                connector.display_name()
+            );
+
             match connector.import(options).await {
                 Ok(mut sessions) => {
+                    let count = sessions.len();
                     all_sessions.append(&mut sessions);
+                    tracing::info!(
+                        "  Imported {} sessions from {}",
+                        count,
+                        connector.display_name()
+                    );
                 }
                 Err(e) => {
                     tracing::warn!("Failed to import from {}: {}", connector.display_name(), e);
@@ -168,12 +183,14 @@ impl ConnectorRegistry {
             // Apply global limit if specified
             if let Some(limit) = options.limit {
                 if all_sessions.len() >= limit {
+                    tracing::info!("Reached global limit of {} sessions", limit);
                     all_sessions.truncate(limit);
                     break;
                 }
             }
         }
 
+        tracing::info!("Total sessions imported: {}", all_sessions.len());
         Ok(all_sessions)
     }
 }
diff --git a/crates/terraphim_sessions/src/connector/native.rs b/crates/terraphim_sessions/src/connector/native.rs
index 5c4f723bb..1d0796670 100644
--- a/crates/terraphim_sessions/src/connector/native.rs
+++ b/crates/terraphim_sessions/src/connector/native.rs
@@ -71,7 +71,12 @@ impl SessionConnector for NativeClaudeConnector {
 
         tracing::info!("Found {} JSONL files", jsonl_files.len());
 
-        for file_path in jsonl_files {
+        let total = jsonl_files.len();
+        for (idx, file_path) in jsonl_files.into_iter().enumerate() {
+            // Log progress every 50 sessions or at the end
+            if idx > 0 && (idx % 50 == 0 || idx == total - 1) {
+                tracing::info!("Imported {}/{} sessions...", idx, total);
+            }
             match self.parse_session_file(&file_path).await {
                 Ok(session) => {
                     if let Some(session) = session {
@@ -98,12 +103,17 @@ impl SessionConnector for NativeClaudeConnector {
             // Apply limit
             if let Some(limit) = options.limit {
                 if sessions.len() >= limit {
+                    tracing::info!("Reached limit of {} sessions, stopping import", limit);
                     break;
                 }
             }
         }
 
-        tracing::info!("Imported {} Claude sessions", sessions.len());
+        tracing::info!(
+            "Imported {} Claude sessions (from {} files)",
+            sessions.len(),
+            total
+        );
         Ok(sessions)
     }
 }
diff --git a/crates/terraphim_sessions/src/service.rs b/crates/terraphim_sessions/src/service.rs
index cdde66a6a..3c4a4fef8 100644
--- a/crates/terraphim_sessions/src/service.rs
+++ b/crates/terraphim_sessions/src/service.rs
@@ -83,7 +83,7 @@ impl SessionService {
 
         if cache_empty {
             tracing::info!("Cache empty, auto-importing sessions...");
-            let options = ImportOptions::new().with_limit(100);
+            let options = ImportOptions::new();
             match self.import_all(&options).await {
                 Ok(sessions) => {
                     tracing::info!("Auto-imported {} sessions", sessions.len());