diff --git a/pkg/cli/gateway_logs.go b/pkg/cli/gateway_logs.go
index 8b3362c54e..2026e7c5f6 100644
--- a/pkg/cli/gateway_logs.go
+++ b/pkg/cli/gateway_logs.go
@@ -140,6 +140,7 @@ func parseGatewayLogs(logDir string, verbose bool) (*GatewayMetrics, error) {
 
 // processGatewayLogEntry processes a single log entry and updates metrics
 func processGatewayLogEntry(entry *GatewayLogEntry, metrics *GatewayMetrics, verbose bool) {
+	gatewayLogsLog.Printf("Processing gateway log entry: event=%s, server=%s, tool=%s", entry.Event, entry.ServerName, entry.ToolName)
 	// Parse timestamp for time range
 	if entry.Timestamp != "" {
 		if t, err := time.Parse(time.RFC3339, entry.Timestamp); err == nil {
@@ -243,6 +244,7 @@ func getOrCreateTool(server *GatewayServerMetrics, toolName string) *GatewayTool
 
 // calculateGatewayAggregates calculates aggregate statistics
 func calculateGatewayAggregates(metrics *GatewayMetrics) {
+	gatewayLogsLog.Printf("Calculating aggregates for %d servers", len(metrics.Servers))
 	for _, server := range metrics.Servers {
 		for _, tool := range server.Tools {
 			if tool.CallCount > 0 {
@@ -378,6 +380,7 @@ func truncateString(s string, maxLen int) string {
 
 // extractMCPToolUsageData creates detailed MCP tool usage data from gateway metrics
 func extractMCPToolUsageData(logDir string, verbose bool) (*MCPToolUsageData, error) {
+	gatewayLogsLog.Printf("Extracting MCP tool usage data from: %s", logDir)
 	// Parse gateway logs
 	gatewayMetrics, err := parseGatewayLogs(logDir, verbose)
 	if err != nil {
@@ -531,6 +534,7 @@ func extractMCPToolUsageData(logDir string, verbose bool) (*MCPToolUsageData, er
 
 // displayAggregatedGatewayMetrics aggregates and displays gateway metrics across all processed runs
 func displayAggregatedGatewayMetrics(processedRuns []ProcessedRun, outputDir string, verbose bool) {
+	gatewayLogsLog.Printf("Aggregating gateway metrics from %d processed runs", len(processedRuns))
 	// Aggregate gateway metrics from all runs
 	aggregated := &GatewayMetrics{
 		Servers: make(map[string]*GatewayServerMetrics),
diff --git a/pkg/cli/interactive.go b/pkg/cli/interactive.go
index 77d4e98251..9eb1bb990f 100644
--- a/pkg/cli/interactive.go
+++ b/pkg/cli/interactive.go
@@ -86,6 +86,7 @@ func CreateWorkflowInteractively(workflowName string, verbose bool, force bool)
 
 // promptForWorkflowName asks the user for a workflow name
 func (b *InteractiveWorkflowBuilder) promptForWorkflowName() error {
+	interactiveLog.Print("Prompting user for workflow name")
 	form := huh.NewForm(
 		huh.NewGroup(
 			huh.NewInput().
@@ -102,6 +103,7 @@ func (b *InteractiveWorkflowBuilder) promptForWorkflowName() error {
 
 // promptForConfiguration organizes all prompts into logical groups with titles and descriptions
 func (b *InteractiveWorkflowBuilder) promptForConfiguration() error {
+	interactiveLog.Print("Prompting user for workflow configuration")
 	// Prepare trigger options
 	triggerOptions := []huh.Option[string]{
 		huh.NewOption("Manual trigger (workflow_dispatch)", "workflow_dispatch"),
@@ -287,6 +289,7 @@ func (b *InteractiveWorkflowBuilder) generateWorkflow(force bool) error {
 
 // generateWorkflowContent creates the workflow markdown content
 func (b *InteractiveWorkflowBuilder) generateWorkflowContent() string {
+	interactiveLog.Printf("Generating workflow content: engine=%s, tools=%v, outputs=%v", b.Engine, b.Tools, b.SafeOutputs)
 	var content strings.Builder
 
 	// Write frontmatter
diff --git a/pkg/cli/trial_repository.go b/pkg/cli/trial_repository.go
index 22112adef5..00e529a64a 100644
--- a/pkg/cli/trial_repository.go
+++ b/pkg/cli/trial_repository.go
@@ -120,6 +120,7 @@ func ensureTrialRepository(repoSlug string, cloneRepoSlug string, forceDeleteHos
 }
 
 func cleanupTrialRepository(repoSlug string, verbose bool) error {
+	trialRepoLog.Printf("Cleaning up trial repository: %s", repoSlug)
 	if verbose {
 		fmt.Fprintln(os.Stderr, console.FormatInfoMessage(fmt.Sprintf("Cleaning up host repository: %s", repoSlug)))
 	}
@@ -139,6 +140,7 @@ func cleanupTrialRepository(repoSlug string, verbose bool) error {
 }
 
 func cloneTrialHostRepository(repoSlug string, verbose bool) (string, error) {
+	trialRepoLog.Printf("Cloning trial host repository: %s", repoSlug)
 	// Create temporary directory
 	tempDir := filepath.Join(os.TempDir(), fmt.Sprintf("gh-aw-trial-%x", time.Now().UnixNano()))