diff --git a/crates/chat-cli/src/cli/chat/context.rs b/crates/chat-cli/src/cli/chat/context.rs
index 89edfb47aa..20dc3f654f 100644
--- a/crates/chat-cli/src/cli/chat/context.rs
+++ b/crates/chat-cli/src/cli/chat/context.rs
@@ -27,6 +27,19 @@ use crate::cli::chat::cli::hooks::HookExecutor;
 use crate::cli::chat::cli::model::ModelInfo;
 use crate::os::Os;
 
+/// Custom serializer that filters out Session paths (which do not support serialization) and only
+/// serializes Agent paths.
+fn serialize_agent_paths_only<S>(paths: &Vec<ContextFilePath>, serializer: S) -> Result<S::Ok, S::Error>
+where
+    S: Serializer,
+{
+    let agent_paths: Vec<&ContextFilePath> = paths
+        .iter()
+        .filter(|path| matches!(path, ContextFilePath::Agent(_)))
+        .collect();
+    agent_paths.serialize(serializer)
+}
+
 #[derive(Debug, Clone)]
 pub enum ContextFilePath {
     /// Signifies that the path is brought in from the agent config
@@ -97,6 +110,8 @@ pub struct ContextManager {
     /// Name of the current active profile.
     pub current_profile: String,
     /// List of file paths or glob patterns to include in the context.
+    /// Session paths are filtered out during serialization to prevent database persistence issues.
+    #[serde(serialize_with = "serialize_agent_paths_only")]
     pub paths: Vec<ContextFilePath>,
     /// Map of Hook Name to [`Hook`]. The hook name serves as the hook's ID.
     pub hooks: HashMap<HookTrigger, Vec<Hook>>,
@@ -457,4 +472,28 @@ mod tests {
             96_000
         );
     }
+
+    #[test]
+    fn test_context_manager_serialization_excludes_session_paths() -> Result<()> {
+        let mut manager = create_test_context_manager(None)?;
+
+        // Add mixed agent and session paths to test filtering
+        manager.paths = vec![
+            ContextFilePath::Agent("config_file.md".to_string()),
+            ContextFilePath::Session("temp_file.md".to_string()),
+        ];
+
+        // Serialization should succeed (no "Session paths are not serialized" error)
+        let serialized = serde_json::to_string(&manager)?;
+
+        // Deserialize to verify structure
+        let deserialized: serde_json::Value = serde_json::from_str(&serialized)?;
+
+        // Check that paths array only contains agent paths
+        let paths_array = deserialized["paths"].as_array().unwrap();
+        assert_eq!(paths_array.len(), 1, "Should serialize only agent paths");
+        assert_eq!(paths_array[0].as_str().unwrap(), "config_file.md");
+
+        Ok(())
+    }
 }
diff --git a/crates/chat-cli/src/cli/chat/conversation.rs b/crates/chat-cli/src/cli/chat/conversation.rs
index 3d064c0180..da88c62dcb 100644
--- a/crates/chat-cli/src/cli/chat/conversation.rs
+++ b/crates/chat-cli/src/cli/chat/conversation.rs
@@ -402,7 +402,9 @@ impl ConversationState {
         });
 
         if let Ok(cwd) = std::env::current_dir() {
-            os.database.set_conversation_by_path(cwd, self).ok();
+            if let Err(e) = os.database.set_conversation_by_path(cwd, self) {
+                tracing::error!("Failed to save conversation to database: {}", e);
+            }
         }
     }
 
diff --git a/crates/chat-cli/src/cli/chat/mod.rs b/crates/chat-cli/src/cli/chat/mod.rs
index 53448af02d..b2f67c19a4 100644
--- a/crates/chat-cli/src/cli/chat/mod.rs
+++ b/crates/chat-cli/src/cli/chat/mod.rs
@@ -670,8 +670,15 @@ impl ChatSession {
         let mut existing_conversation = false;
         let previous_conversation = std::env::current_dir()
             .ok()
-            .and_then(|cwd| os.database.get_conversation_by_path(cwd).ok())
-            .flatten();
+            .and_then(|cwd| {
+                match os.database.get_conversation_by_path(cwd) {
+                    Ok(conv) => conv,
+                    Err(e) => {
+                        tracing::warn!("Failed to load conversation from database: {}", e);
+                        None
+                    }
+                }
+            });
 
         // Only restore conversations where there were actual messages.
         // Prevents edge case where user clears conversation then exits without chatting.
diff --git a/crates/chat-cli/src/cli/mod.rs b/crates/chat-cli/src/cli/mod.rs
index 1e384cf63e..18dc42a606 100644
--- a/crates/chat-cli/src/cli/mod.rs
+++ b/crates/chat-cli/src/cli/mod.rs
@@ -146,7 +146,9 @@ impl RootSubcommand {
 
         // Daily heartbeat check
         if os.database.should_send_heartbeat() && os.telemetry.send_daily_heartbeat().is_ok() {
-            os.database.record_heartbeat_sent().ok();
+            if let Err(e) = os.database.record_heartbeat_sent() {
+                tracing::warn!("Failed to record heartbeat in database: {}", e);
+            }
         }
 
         // Send executed telemetry.
diff --git a/crates/chat-cli/src/telemetry/cognito.rs b/crates/chat-cli/src/telemetry/cognito.rs
index 4c541f508d..075ff39ea1 100644
--- a/crates/chat-cli/src/telemetry/cognito.rs
+++ b/crates/chat-cli/src/telemetry/cognito.rs
@@ -55,7 +55,9 @@ pub async fn get_cognito_credentials_send(
             "no credentials from get_credentials_for_identity",
         ))?;
 
-    database.set_credentials_entry(&credentials).ok();
+    if let Err(e) = database.set_credentials_entry(&credentials) {
+        tracing::warn!("Failed to save credentials to database: {}", e);
+    }
 
     let Some(access_key_id) = credentials.access_key_id else {
         return Err(CredentialsError::provider_error("access key id not found"));